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List of Organic Chemistry Books

By: Pharma Tips | Views: 27451 | Date: 19-Feb-2013

Advanced Organic Chemistry has maintained its place as the premier textbook in the field, since its first appearance in 1977. It offers broad coverage of the structure, reactivity and synthesis of organic compounds. As in the earlier editions, the text contains extensive references to both the primary and review literature and provides examples of data and reactions that illustrate and document the generalizations. While the text assumes completion of an introductory course in organic chemistry, it reviews

Textbook of Organic Chemistry



Title Textbook of Organic Chemistry
Subtitle
Author Rakesh K. Parashar, V.K. Ahluwalia
ISBN 9788130917740
List price Rs. 395.00
Original price
Binding Paperback
No of pages 504
Book size . mm
Publishing year 2012
Original publisher Viva Books Private Limited
Published in India by Viva Books Private Limited
Exclusive distributors Viva Books Private Limited
Sales territory Worldwide
Status New Arrival


Description: Textbook of Oragnic Chemistry provides easy access to the core information in the feild and makes a comprehensive approach to desseminate information in a clear and systematic manner. The book is presented and organized in a way to discourage students from rote learning. It covers all the topics in Organic Chemistry included in the sylabi of Indian universities for undergraduate courses. Special emphasis is given to the basic concepts viz. acids and bases, hybridization and resonance. Functional groups, which are extremely important for the understanding of Organic Chemisrty, have been dicussed along with the hydrocarbons and the organometallic compounds. Other important topics covered include sulfur compounds, oxidations and reductions. All the important topics are represented in a format which is ideal for learning and rapid revision.

Contents: Chapter 1 The Fundamental Concepts • Atomic Orbital • Electronic Configuration • Hybridization • Shape and Structure of Simple Molecules • Structural Formula • Dipole Moment and Electronegativity • Hydrogen Bonding • Steric Hindrance • Resonance • Chapter 2 Acids and Bases • Arrhenius Concept • Bronsted–Lowry Concept • Lewis Concept • Strength of Acids • Strength of Bases • Electronegativity • Inductive Effect • Resonance • Chapter 3 Reaction Mechanism and Reaction Intermediates • Reaction Mechanism • Reactivity of Substrate • Bond Fission • Reaction Intermediates • Reagents • Types of Reactions: Substitution Reaction, Addition Reaction, Elimination Reaction,Rearrangement Reaction • Chapter 4 Stereochemistry • Introduction • Isomerism: Structural Isomerism, Stereoisomerism • Chapter 5 Functional Groups • Introduction • Types of Functional Groups • Important Families of Organic Compounds • Chapter 6 Alkanes and Cycloalkanes • Introduction • Alkanes • Cycloalkanes • Chapter 7 Alkenes • Introduction • Nomenclature • Structure • Physical Properties • Preparation • Reactions • Test for Alkenes • Chapter 8 Alkynes • Introduction • Nomenclature • Structure • Physical Properties • Preparation • Reactions • Chapter 9 Aromatic Hydrocarbons • Introduction • Aromaticity • Preparation • Structure • Stability • Physical Properties • Chemical Properties • Nomenclature of Substituted Benzenes • Preparation of Monosubstituted Benzenes • Reactivity and Orientation of Monosubstituted Benzenes • Anomalous Behavior of Haloarenes • Chapter 10 Alkyl Halides and Aryl Halides • Introduction • Nomenclature • Physical Properties • Preparation • Reactions of Alkyl Halides • Reactions of Aryl Halides • Tests • Chapter 11 Organometallic Compounds • Introduction • Nomenclature • Structure and Bonding • Preparation of Grignard Reagent • Reactions of Grignard Reagent • Preparation of Alkyl lithium • Preparation of Lithium Dialkylcuprate • Preparation of Organozinc • Summary of Reactions of Grignard • Reagent • Chapter 12 Alcohols and Phenols • Introduction • Nomenclature • Physical Properties • Preparation of Alcohols • Preparation of Phenols • Reactions of Alcohols • Tests to Distinguish 1º, 2º and 3º Alcohols • Reactions of Phenols • Test for Phenols • Chapter 13 Ethers and Epoxides • Introduction • Ethers • Crown Ethers • Epoxides • Chapter 14 Amines and Diazonium SaltsAmines • Introduction • Nomenclature • Classification • Structure • Physical Properties • Preparation • Reactions • Tests for Amines and Separation of 1º, 2° and 3° Amines • Diazonium Salts • Nomenclature • Diazotization • Reactions • Use of Diazonium Salts in Organic Synthesis • Chapter 15 Nitriles and Isonitriles • Introduction • Nitriles • Nomenclature • Preparation • Structure • Reactions • Isonitriles • Structure • Reactions • Chapter 16 Aldehydes and Ketones • Introduction • Nomenclature • Structure • keto–enol Tautomers • Physical Properties • Preparation • Reactions • Test for Carbonyl Group • Tests for Aldehyde • Test for Ketones • Chapter 17 Carboxylic Acids and Their Derivatives • Introduction • Carboxylic Acids • Carboxyl Group • Nomenclature • Preparation • Physical Properties • Reactions • Derivatives of Carboxylic Acids • Acid Chlorides • Acid Anhydrides • Esters • Amides • Order of Reactivity of Carboxylic Acid Derivatives • Chapter 18 Sulfur CompoundsIntroduction • Oxidation States • Nomenclature • Applications • Thiols or Mercaptans • Physical Properties • Structure • Preparation • Reactions • Thioethers or Sulfides • Preparation • Reactions • Chapter 19 Oxidation • Introduction • Oxidizing Agents • Manganese(VII) Oxidants • Chromium(VI) Oxidants • Peracids • Miscellaneous Oxidants • Oxidation of Individual Functional Groups • Oxidation of Hydrocarbons • Oxidation of Alcohols • Oxidation of Phenols • Oxidation of Aldehydes • Oxidation of Ketones • Oxidation of Amines • Chapter 20 Reduction • Introduction • Reducing Agents • Reduction of Individual Functional Groups • Reduction of Unsaturated Hydrocarbons • Reduction of Aromatic Hydrocarbons • Reduction of Alcohols and Phenols • Reduction of Aldehydes and Ketones • Reduction of Carboxylic Acids • Reduction of Nitro Compounds and Nitriles • Index.

About the authors: Rakesh K. Parashar completed his Ph.D. form the University of Delhi in 1990in the area of Synthetic Organic Chemistry. Subsequently he pursued his post-doctorate from the University of Barcelona, Spain. He has published 25 papers in national and international journals of high repute. He has also delivered several lectures in India and abroad. He is the author of 6 books published by various Indian and international publishing houses.

Dr. Parashar holds the position of Associate Professor at the Department of Chemistry, Kirori Mal College, University of Delhi. He ahs been teaching undergraduate students and postgraduate students since 1990 and has research experience of more than 20 years.

V.K. Ahluwalia is a retired professor from the Chemistry Department, University of Delhi, Delhi. He ahs published 300 research papers and a large number of books.


Advanced Organic Chemistry

Francis A. Carey, Richard A. Sundberg

Part A:
Paperback, 1199 Pages
5th Edition, 2007
ISBN-13: 978-0-387-44897-8
Springer

Francis A. Carey, Richard A. Sundberg

Part B:
Paperback, 1322 Pages
5th Edition, 2007
ISBN-13: 978-0-387-68350-8
Springer

Description

  • Parts A and B may stand alone; together, they provide a comprehensive foundation for the study in organic chemistry
  • Updated material reflecting scientific advances since 2001’s Fourth Edition, especially in computational chemistry
  • Companion Websites provide digital models for students and exercise solutions for instructors

Advanced Organic Chemistry has maintained its place as the premier textbook in the field, since its first appearance in 1977. It offers broad coverage of the structure, reactivity and synthesis of organic compounds. As in the earlier editions, the text contains extensive references to both the primary and review literature and provides examples of data and reactions that illustrate and document the generalizations. While the text assumes completion of an introductory course in organic chemistry, it reviews the fundamental concepts for each topic.

This two-part, fifth edition has been substantially revised and reorganized for greater clarity. The control of reactivity to achieve specific syntheses is one of the overarching goals of organic chemistry. Part B describes the most general and useful synthetic reactions, organized on the basis of reaction type. It can stand-alone; together, with Part A: Structure and Mechanisms, the two volumes provide a comprehensive foundation for the study in organic chemistry.

Editorial Review

Advanced Organic Chemistry” by Francis A. Carey and Richard J. Sundberg – the well-known textbook for graduate students – has now appeared in a 5th edition. The book is divided into two parts: “Part A” with the fundamentals of the structure of organic compounds and mechanisms, and “Part B” with specific reactions. Thus, this review is likewise divided into two sections.

Part A: Structure and Mechanisms

Once again, Part A contains important information on the fundamentals of organic chemistry, and in contrast to the usual beginner textbooks, it always elaborates beyond the introductions with additional information that will likely confuse beginners. For example, the chapter on orbitals and molecular orbitals is relatively long, and also describes the basics of computer-generated representations with the help of DFT (Density Functional Theory).

In later chapters as well, for topics such as “Nucleophilic Substitution” that are also found in other textbooks, Carey & Sundberg present a detailed treatment that gleams with a multitude of examples.

Part A is recommended reading for all students who have already worked their way through an organic chemistry book. Carey & Sundberg can help to refresh and embellish their existing knowledge, which makes the book especially worthwhile when preparing to complete a degree.

Part B: Reactions and Synthesis

Part B describes the important reactions of organic chemistry. The chapters are organized according to reaction type, e.g. “Reactions of Carbon Nucleophiles with Carbonyl Compounds” or “Reduction of Carbon-Carbon Multiple Bonds”. Each chapter contains mechanistic details and basic principles, but also a plethora of additional examples with the corresponding literature citations. In principle, Part B could be considered a collection of reviews. The breadth of scope in the individual chapters is similar to that in articles that might be found in Chem. Rev., for example. The literature has been covered far beyond the year 2000. Although not all of the important publications have been covered, the ones selected will enable the student to identify the potential and applicability of a given transformation.

Parts A and B are quite comprehensive, and being so up to date makes them extremely useful throughout the reader’s academic career. However, Carey & Sundberg assumes a basic understanding of organic chemistry, without which some students might not be able to cope with the sheer volume of information, or will find it difficult to access the information that is the most relevant to their specific academic study.

Carey & Sundberg will be interesting to all students who seek a detailed understanding of organic chemistry, and who wish to refresh and embellish their existing knowledge. On the strength of the scope and quality of the explanations, this pair of texts is recommended for use as the resource of first resort for specific research questions in one’s later career.

Chirality in Drug Research

Eric Francotte, Wolfgang Lindner

Hardcover, 351 Pages
First Edition, 2006
ISBN: 3-527-31076-2
Wiley-VCH

Description

Divided into the three main sections of synthesis, analysis and drug development, this handbook covers all stages of the drug development process, including large-scale synthesis and purification of chirally pure pharmaceuticals.

The two editors from academia and a major pharmaceutical company have assembled an experienced, international team who provide first-hand practical advice and report previously unpublished data.

In the first section, the isolation of chiral drugs from natural sources, their production in enzymatic processes and the resolution of racemic mixtures in preparative chromatography are outlined in separate chapters. For the section on qualitative and quantitative analysis, enantioselective chromatographic methods are presented as well as optical methods and CE-MS, while the final section deals with the pharmacology, pharmacokinetics and metabolic aspects of chiral drugs, devoting whole chapters to stereoselective drug binding and modeling chiral drug-receptor interactions.

With its unique industry-relevant aspects, this is a must for medicinal and pharmaceutical chemists.

Editorial Review

One reason behind the trend for medications to contain an active drug in the most enantiomerically enriched form possible is the availability of better methods for enantioselective synthesis and characterization. However, a greater knowledge of the biology involved is far more significant, as exemplified in particular by the tragic thalidomide episode, and this has led to paradigm shifts both in the industry and on approval boards. The other enantiomer frequently amounts only to so much inactive dead weight, while a number of such enantiomers are responsible for side effects; only in a few cases have specific compositions of a racemate or an enantiomeric pair demonstrated a synergistic effect.

During the actual development process, the question invariably arises of which step and which method to choose for introducing enrichment. Thus racemates are produced by parallel synthesis for drug candidates - it makes sense to resolve the racemate for the initial animal studies, whereas an optimized, enantioselective synthesis is employed in the course of production. These steps go hand in hand, so that the initial experiences in optimization (method development for analysis, and for synthesis and purification) are transferred directly into the next stage of development.

The book “Chirality in Drug Research” explains in detail why enantiomers should be considered as completely different drugs as a matter of principle, and provides a good and easily understood survey of the most important methods used in industry for the manufacture and analysis of drugs. It is indeed difficult for a single book to cover all of the different stages of development, all the way from the milligram-scale up to tonnes, but the present work appears to have succeeded in this regard. This monograph is ideal in that it provides an overview of the methods and technologies currently in use, and refers the reader to cited literature for more in-depth study where necessary. It can facilitate collaborations between the individual work groups involved in development, since all of the important principles and options are introduced. This work’s interdisciplinary character is also a boon for advanced students, making it an interesting read for those who wish to gain a greater familiarity with this area. “Chirality in Drug Research” provides its readers with a comprehensive overview of the field, and offers a simultaneous, integrated exposure to the important methods for both synthesis and analysis.

Contents

1 Chiral Drugs from a Historical Point of View (Joseph Gal).
2 Stereoselective Synthesis of Drugs – An Industrial Perspective (Hans-Jürgen Federsel).
3 Aspects of Chirality in Natural Products Drug Discovery (Philipp Krastel, Frank Petersen, Silvio Roggo, Esther Schmitt, and Ansgar Schuffenhauer).
4 Biotransformation Methods for Preparing Chiral Drugs and Drug Intermediates (Michael Müller and Marcel Wubbolts).
5 Resolution of Chiral Drugs and Drug Intermediates by Crystallisation (Kazuhiko Saigo).
6 Isolation and Production of Optically Pure Drugs by Enantioselective Chromatography (Eric Francotte).
7 Stereoselective Chromatographic Methods for Drug Analysis (Norbert M. Maier and Wolfgang Lindner).
8 Capillary Electrophoresis Coupled to Mass Spectrometry for Chiral Drugs Analysis (Serge Rudaz and Jean-Luc Veuthey).
9 Powerful Chiral Molecular Tools for Preparation of Enantiopure Alcohols and Simultaneous Determination of Their Absolute Configurations by X-Ray Crystallography and/or 1H NMR Anisotropy Methods (Nobuyuki Harada).
10 Keywords in Chirality Modeling Molecular Modeling of Chirality – Software and Literature Research on Chirality in Modeling, Chirality in Docking, Chiral Ligand–Receptor Interaction and Symmetry (Gerd Folkers, Mine Yarim, and Pavel Pospisil).


 

Fundamentals of Heterocyclic Chemistry: Importance in Nature and in the Synthesis of Pharmaceuticals

Louis D. Quin, John Tyrell

Hardcover, 327 Pages
1st Edition, 2010
ISBN: 978-0-470-56669-5
Wiley-Interscience

Description

  • Heterocyclic chemistry is of prime importance as a sub-discipline of Organic Chemistry, as millions of heterocyclic compounds are known with more being synthesized regularly
  • Introduces students to heterocyclic chemistry and synthesis with practical examples of applied methodology
  • Emphasizes natural product and pharmaceutical applications
  • Provides graduate students and researchers in the pharmaceutical and related sciences with a background in the field
  • Includes problem sets with several chapters

Editorial Review

Hundreds of thousands of natural products and pharmaceutical active ingredients contain heterocycles as central building blocks. Despite their importance, the nomenclature, properties and synthesis is given little coverage in most textbooks. Louis D. Quin and John Tyrell attempt to close this gap with "Fundamentals of Heterocyclic Chemistry: Importance in Nature and in the Synthesis of Pharmaceuticals".

The text is easily understood even with a basic knowledge of organic chemistry, and achieves a good balance between background information and concise facts. The importance of heterocycles is demonstrated at the outset with innumerable natural products; this is followed with information on the nomenclature, properties and synthesis of the most important heterocycle classes. For example, the chapter on nomenclature is quite successful, and the rules are described a little at a time over several pages. The properties and syntheses of heterocycles are also explained gradually, which means that the complexity increases in successive chapters. Some of the reactions are explained mechanistically so that the students can easily understand.

The authors have made good selections among the important heterocycles and synthesis options, and thus have decided to limit the scope and complexity of the book. As a textbook, "Fundamentals of Heterocyclic Chemistry: Importance in Nature and in the Synthesis of Pharmaceuticals" is a highly successful work. Furthermore, for synthesis chemists coming into contact with heterocycles for the first time in their professional lives, this book offers the opportunity to acquire broad knowledge within a short period of time.

The single point of criticism is the structural formulas, which often seem to have been prepared too quickly. For example, the bond stereochemistry is left out in some compounds, which can be overlooked given that a focus on enantioselective syntheses has likewise been left out. Especially considering the buyer-friendly price and readily understandable text, this book comes highly recommended!

Contents

Chapter 1 THE SCOPE OF THE FIELD OF HETEROCYCLIC CHEMISTRY.
Chapter 2 COMMON RING SYSTEMS AND THE NAMING OF HETEROCYCLIC COMPOUNDS.
Chapter 3 NATURE AS A SOURCE OF HETEROCYCLIC COMPOUNDS.
Chapter 4 PRINCIPLES OF SYNTHESIS OF AROMATIC HETEROCYCLES BY INTRAMOLECULAR CYCLIZATION.
Chapter 5 SYNTHESIS OF HETEROCYCLIC SYSTEMS BY CYCLOADDITION REACTIONS.
Chapter 6 AROMATICITY AND OTHER SPECIAL PROPERTIES OF HETEROCYCLES: PI-DEFICIENT RING SYSTEMS.
Chapter 7 AROMATICITY AND OTHER SPECIAL PROPERTIES OF HETEROCYCLES: PI-EXCESSIVE RING SYSTEMS AND MESOIONIC RING SYSTEMS.
Chapter 8 THE IMPORTANCE OF HETEROCYCLES IN MEDICINE.
Chapter 9 SYNTHETIC METHODS FOR SOME PROMINENT HETEROCYCLIC FAMILIES: EXAMPLES OF PHARMACEUTICALS SYNTHESIS.
Chapter 10 GEOMETRIC AND STEREOCHEMICAL ASPECTS OF NONAROMATIC HETEROCYCLES.
Chapter 11 SYNTHETIC HETEROCYCLIC COMPOUNDS IN AGRICULTURAL AND OTHER APPLICATIONS.

March's Advanced Organic Chemistry. Reactions, Mechanisms, and Structure

Michael B. Smith, Jerry March

Hardcover, 2384 Pages
6th Edition, 2007
ISBN: 978-0-471-72091-1
Wiley

Description

New to this Fifth Edition:
Michael Smith from the University of Connecticut joins as coauthor for the Fifth Edition
Contains 20,000 valuable, selected references to the primary literature–5,000 new to this edition
40 entirely new sections covering the most important developments in organic chemistry since the previous edition
Updated illustrations of molecular structures

Editorial Review

The "March" is a useful and extensive book, in order to receive a fast overview of topics of the organic chemistry. Literature references help to find relevant, profound articles.

As a textbook, it does contain too much information, and current new up-to-date reactions are not included. But the March earned due to its topic varieties and balance, and the numerously existing key words quite the descriptor "Encyclopedia". And a good encyclopedia belongs into the bookshelf of every organic chemist!

Contents

Bibliographical Note.
Abbreviations.
PART 1.
Localized Chemical Bonding.
Delocalized Chemical Bonding.
Bonding Weaker than Covalent.
Stereochemistry.
Carbocations, Carbanions, Free Radicals, Carbenes, and Nitrenes.
Mechanisms and Methods of Determining Them.
Photochemistry.
Acids and Bases.
Effects of Structure on Reactivity.
PART 2.
Aliphatic Nucleophilic Substitution.
Aromatic Electrophilic Substitution.
Aliphatic Electrophilic Substitution.
Aromatic Nucleophilic Substitution.
Free-Radical Substitution.
Addition to Carbon-Carbon Multipe Bonds.
Addition to Carbon-Hetero Multipe Bonds.
Eliminations.
Rearrangements.
Oxidations and Reductions.
Appendix A: The Literature of Organic Chemistry.
Appendix B: Classification of Reactions by Type of Compound Synthesized.
Author Index.
Subject Index.

Modern Organic Synthesis - An Introduction

George S. Zweifel, Michael H. Nantz

Softcover, 504 Pages
1st Edition, 2007
ISBN: 978-0-716-77266-8
W. H. Freeman

Description

Written for the organic synthesis portion of the advanced organic chemistry course (taken by seniors and graduate students), Zweifel and Nantz’s concise new text covers the essentials with exceptional coherence and clarity without bogging students down with too much unnecessary material.

Editorial Review

"Modern Organic Synthesis - An Introduction" is aimed at advanced students who have already completed an introductory course in organic chemistry and who would now like to deepen their understanding. With this basic knowledge as a foundation, the authors attempt to define important tactics and reactions as well as reagents, a goal which they attain quite well. Chapters on synthetic design and stereochemical considerations in synthesis planning, as well as ideas for the protection of functional groups, provide well-focused illustrations of fundamental approaches. The language is readily understandable, and the topics are well supported by interesting concrete examples. What stands out is that the authors make a substantial effort to mention a variety of reaction conditions and reagents with which delicate transformations can be carried out selectively. The selective protection of polyfunctional molecules, or examples of the oxidation and reduction of functional groups in the presence of other groups, are described in detail.

In comparison to old-fashioned textbooks that are strictly organized into sections by substance class or reaction mechanism, the chapters in this book are more freely arranged and are self-contained. The diversity of topics is not as broad as in other organic textbooks for advanced students, some of which exceed one thousand pages. But the authors have clearly succeeded in selecting important themes and focusing on an assortment of synthesis variants.

In addition, the book does not require a linear reading; rather, one can delve deeply into specific topics of interest. In "Modern Organic Synthesis - An Introduction", one can find several examples and absorbing commentary that help to deepen one’s existing comprehension and to link it with detailed knowledge. Since the authors often achieve this by providing concrete advice on reagents and reaction conditions backed up by literature citations, the reader will also find it beneficial to consult this work in addressing specific synthesis problems. In this way, "Modern Organic Synthesis - An Introduction" is a worthwhile book for advanced students, who will still find it useful in their later professional careers.

Contents

1. Synthetic Design
1.1 Retrosynthetic Design
1.2 Reversal of the Carbonyl Group Polarity (Umpolung)
1.3 Steps in Planning a Synthesis
1.4 Choice of Sythetic Method
1.5 Domino Reactions
1.6 Computer-Assisted Retrosynthetic Analysis

2. Stereochemical Considerations in Planning Synthesis
2.1 Conformational Analysis
2.2 Evaluation of Nonbonded Interactions
2.3 Six-Member Hetercyclic Systems
2.4 Polycyclic Ring Systems
2.5 Cyclohexyl Systems with sp2-Hybridized Atoms
2.6 Significant Energy Difference
2.7 Computer-Assisted Molecular Modeling
2.8 Reactivity and Product Determination as a Function of Conformation

3. The Concept of Protecting Functional Groups
3.1 Protection of NH Groups
3.2 Protection of OH Groups of Alcohols
3.3 Protection of Diols as Acetals
3.4 Protection of Carbonyl Groups in Aldehydes and Ketones
3.5 Protection of the Carboxyl Group
3.6 Protection of Double Bonds
3.7 Protection of Triple Bonds

4. Functional Group Transformations: Oxidation and Reduction
4.1 Oxidation of Alcohols to Aldehydes and Ketones
4.2 Reagents and Procedures of Alcohol Oxidation
4.3 Chemoselective Agents for Oxidizing Alcohols
4.4 Oxidation of Acyloins
4.5 Oxidation of Tertiary Allylic Alcohols
4.6 Oxidative Procedures to Carboxylic Acids
4.7 Allylic Oxidation of Alkenes
4.8 Terminology for Reduction of Carbonyl Compounds
4.9 Nucleophilic Reducing Agents
4.10 Electrophilic Reducing Agents
4.11 Regio- and Chemoselective Agents
4.12 Diastereoselective Reductions of Cyclic Ketones
4.13 Inversion of Secondary Alcohol Stereochemistry
4.14 Diastereofacial Selectivity in Acyclic Systems
4.15 Enantioselective Reductions

5. Functional Group Transformations: The Chemistry of Carbon-Carbon pi-Bonds and Related Reactions
5.1 Reactions of Carbon-Carbon Double Bonds
5.2 Reactions of Carbon-Carbon Triple Bonds

6. Formation of Carbon-Carbon Single Bonds
6.1 1,3-Dicarbonyl and Related Compounds
6.2 Direct Alkylation of Simple Enolates
6.3 Cyclization Reactions--Baldwin's Rules for Ring Closure
6.4 Stereochemistry of Cyclic Ketone Alkelation
6.5 Imine and Hydrazone Anions
6.6 Enamines
6.7 The Aldol Reaction
6.8 Condensation Reactions of Enols and Enolates
6.9 Robinson Annulation

7. Formation of Carbon-Carbon Bonds Via Organometallic Reagents
7.1 Organolithium Reagents
7.2 Organomagnesium Reagents
7.3 Organotitanium Reagents
7.4 Organocerium Reagents
7.5 Organocopper Reagents
7.6 Organochromium Reagents
7.7 Organozinc Reagents
7.8 Organoboron Reagents
7.9 Organosilicon Reagents
7.10 Palladium-Catalyzed Coupling Reactions

8. Formation of Carbon-Carbon pi-Bonds
8.1 Formation of Carbon-Carbon Double Bonds
8.2 Formation of Carbon-Carbon Triple Bonds

9. Synthesis of Carbocyclic Systems
9.1 Intramolecular Free Radical Cyclizations
9.2 Cation-pi Cyclizations
9.3 Pericyclic Reactions
9.4 Ring-Closing Olefin Metathesis (RCM)

10. The Art of Synthesis

Abbreviations
Answers to Select End-of-Chapter Problems
Index

Molecules that changed the World

K. C. Nicolaou, Tamsyn Montagnon

Hardcover, 385 Pages
First Edition, 2008
ISBN: 978-3-527-30983-2
Wiley-VCH

Description

In this delightfully designed book, K. C. Nicolaou introduces the world's most important molecules and shows in a fascinating way the role certain compounds have to play in our everyday lives in the fields of drugs, aromatics or vitamins. For example, he tells the story of Aspirin, beginning 3,500 years ago in Egypt, through to its first synthesis and various applications with many entertaining facts and details. Printed in full color throughout and with its oversize format, this is a must for every chemist, natural scientist and anyone interested in the sciences.

Editorial Review

K. C. Nicolaou, the author of the "Classics in Total Synthesis" series, has collaborated with Tamsyn Montagnon as coauthor to produce a work that is unique in many respects. The graphic and color composition as well as the format are unusual, and are oriented toward readers who are interested in natural products and drugs as well as organic chemistry, but who are put off by the textbooks that are heavier on text with a more prosaic appearance. The pictures are artfully arranged, and occupy approximately half the page space. The color scheme is decent, although the orange-colored background of the cyclic compounds can certainly take some getting used to. In this way, the book is refreshingly different, and will pique the interest of a rather broad range of readers.

The actual content includes the following. The historical development of organic synthesis is acknowledged in many places. Additional focus is placed on chemists whose work is significant for the science of synthesis. The authors use numerous photographs to give these scientists a face, with which the reader learns how different walks of life or external factors were significant for a specific synthesis. This makes the scientists come to life, and makes the book exceptionally interesting to read. The critical reader will find the pictorial presentations to smack of hero worship. At the same time, the difficulties that underlie the development are given shorter shrift. For these reasons, "Molecules that changed the World" forms a counterpoint to the same publisher’s "The Way of Synthesis", by Hudlický und Reed. This latter work offers a different picture, with critical observations and a detailed analysis of the problems in the development of various synthetic pathways to a specific molecule. Where "The Way of Synthesis" presents the fierceness of the competition between research groups, even to the extent of detailed explanations of synthesis steps and how difficult was the optimization, the book by Nicolaou and Montagnon celebrates the important driving forces.

The fact that some of the drugs from pharmaceutical preparations are mentioned in connection with principles from molecular biology lends an additional dimension to the book. If this is a tribute to an industry that has co-financed the book, then this is a price that I am pleased to pay. The interested reader can make a better connection to a known blockbuster from the pharmaceutical industry than to a maritime natural product that is considered to be interesting from the synthetic tactics point of view by virtue of its structural complexity, but this tends to limit the target readership. The book coveys to readers the message that organic chemistry and synthetic tactics have developed over several hundred years, and that important natural products and drugs are associated with the individuals who were substantially responsible for the development of their synthesis. This lends a human and positive picture in society to an otherwise dry science. If the aim of the authors were to improve the perception of “chemistry” in society, then they have succeeded, and the attractive price will hopefully foster a wide dissemination of this book.

Enthusiasts and students with a serious interest in organic chemistry will find some interesting stories and explanations herein. The reader who is mainly interested in the historical development of the science will probably find the complexity of the molecules presented to be interesting, but nothing of further use. In any case, the book makes a wonderfully suitable gift for anyone who is interested in chemistry, and will serve to enhance that fascination and interest.

Contents

Chapter 1. Introduction: Atoms, Molecules & Synthesis.
Chapter 2. Urea & Acetic Acid.
Chapter 3. Glucose.
Chapter 4. Aspirin.
Chapter 5. Camphor.
Chapter 6. Terpineol.
Chapter 7. Tropinone.
Chapter 8. Haemin.
Chapter 9. Quinine.
Chapter 10. Morphine.
Chapter 11. Steroids & the Pill.
Chapter 12. Strychnine.
Chapter 13. Penicillin.
Chapter 14. Longifolene.
Chapter 15. Prostaglandins & Leukotrienes.
Chapter 16. Vitamin B12.
Chapter 17. Erythronolide B & Erythromycin A.
Chapter 18. Monensin.
Chapter 19. Avermectin.
Chapter 20. Amphotericin B.
Chapter 21. Ginkgolide B.
Chapter 22. Cyclosporin, FK506 & Rapamycin.
Chapter 23. Calicheamicin γ1I.
Chapter 24. Palytoxin.
Chapter 25. Taxol.
Chapter 26. Mevacor, Zaragozic Acids & CP Molecules.
Chapter 27. Brevetoxin B.
Chapter 28. Ecteinascidin 743.
Chapter 29. Epothilones.
Chapter 30. Resiniferatoxin.
Chapter 31. Vancomycin.
Chapter 32. Thiostrepton.
Chapter 33. Small Molecule Drugs.
Chapter 34. Biologics.

Name Reactions and Reagents in Organic Synthesis

Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro

Hardcover, 882 Pages
2nd Edition, April 2005
ISBN: 0-471-22854-0
Wiley-Interscience

Description

This Second Edition is the premier name resource in the field. It provides a handy resource for navigating the web of named reactions and reagents. Reactions and reagents are listed alphabetically, followed by relevant mechanisms, experimental data (including yields where available), and references to the primary literature. The text also includes three indices based on reagents and reactions, starting materials, and desired products. Organic chemistry professors, graduate students, and undergraduates, as well as chemists working in industrial, government, and other laboratories, will all find this book to be an invaluable reference.

Editorial Review

It has taken 17 years for the second edition of “Name Reactions and Reagents in Organic Synthesis” to appear. With the mounting curiosity over such a period, this book is certain to receive an exacting appraisal.

To come right to the point, the huge number of name reactions and reagents is really quite impressive. There is far more involved than minor revision, since a great many new transformations that have been developed over the intervening time now find their way into the book. The amount of detailed work by these authors is simply amazing! Each reaction is covered on two pages, typically presented with a reaction scheme, one mechanism, and four current examples from the literature (up to the year 2005), which is a powerful springboard for further inquiry.

Unfortunately, the explanations of some of the reactions come up a bit short. The authors themselves recommend that readers, "Feel free to write in the text... transform this into your book of Name Reactions! It is intended to serve as a starting point". This reviewer whole-heartedly agrees with such an approach - the monograph is an excellent “starting point”. Books that include more text tend to promote incorrect or outmoded conclusions that end up being refuted at length by later literature reports. A reader may feel more secure consulting a lengthier text, without really interacting with the material. A spare presentation is a big plus for some readers, though, who prefer to acquire the fundamentals with the help of such a compendium, and then consult the current literature for a more in-depth understanding.

As each of the reactions and reagents are treated within a relatively brief space, an unbelievable number of transformations are found within these 882 pages. What’s more, there are descriptions of a number of chemicals such as TBAF that wouldn’t necessarily be considered name reagents, and many other abbreviations and acronyms are included. Thus, the scope of the information available from “Name Reactions and Reagents in Organic Synthesis” is much larger than one might expect from a run of the mill monograph on name reactions. This work is too comprehensive to be purely a textbook, even though it is excellent value for the money, but it will play a significant role as a reference work in the academic and professional realm.

Name Reactions. A Collection of Detailed Reaction Mechanisms

Jie Jack Li

Hardcover, 621 Pages
4th Edition, 2009
ISBN: 978-3-642-01052-1
Springer, Berlin

Description

This book differs from others on name reactions in organic chemistry by focusing on their mechanisms. It covers over 300 classical as well as contemporary name reactions. Biographical sketches for the chemists who discovered or developed those name reactions have been included. Each reaction is delineated by its detailed step-by-step, electron-pushing mechanism, supplemented with the original and the latest references, especially review articles. This book contains major improvements over the previous edition and the subject index is significantly expanded.

Editorial Review

"Name Reactions - A collection of Detailed Reaction Mechanisms" has been expanded significantly as compared to the Second Edition. The book contains a multitude of new name reactions and, and as a new feature, reaction examples from the current literature..

Each name reaction is illustrated with a reaction scheme, an accurate and detailed mechanism, and two interesting examples from current work. In addition, numerous up-to-date citations are provided that can facilitate an initial literature search. The textual explanations are quite concise, and in most cases are confined to the reaction schemes. For a few of the name reactions, the references also include biographical information on the originator of the reaction, which makes quite interesting reading.

Space is used more effectively in the new version, in contrast to the Second Edition, and pages are filled with content. The author has taken great pains in this respect, as well as in ensuring that the literature citations are up to date. The level of detail varies a great deal in some places, though this might simply reflect the author’s own areas of interest. For example, coverage of the "Staudinger Ketene Cycloaddition" is limited to a consideration of the transition state.

"Name Reactions" is an especially useful book for obtaining a first introduction to a multitude of important and also current name reactions. Moreover, the mechanistic explanations in the form of excellent schemes provide a basis for advanced students to practice these mechanisms. A number of errors from the Second Edition have been corrected, and this fact together with the successful enhancements make a good case for purchasing this latest edition.

Organic Chemistry

Paula Y. Bruice

Hardcover, 1440 Pages
6th Edition, 2010
ISBN: 978-0-321-66313-9
Prentice Hall

Description

This innovative text is organized in a way that discourages rote memorization, by emphasizing what functional groups do rather than how they are made, highlighting mechanistic similarities and tying synthesis and reactivity together. Bruice's writing has been praised for anticipating students' questions, appealing to their visual and problem solving needs. The text balances coverage of traditional topics with bioorganic chemistry, recognizing the importance of bioorganic topics to today's students.

Editorial Review

Paula Bruice’s textbook is noteworthy among the organic chemistry textbooks described here in that its language is easily understandable, and its numerous illustrations and well-crafted design offer students an easier introduction to organic chemistry. The author herself remarks that the subject should by no means be viewed as a foreign language in which one must learn to use a vocabulary of thousands of reactions. Rather, what should be conveyed are fundamentals and relationships that can be applied in principle even to complicated reactions – a task in which the author succeeds admirably.

The reason is the somewhat loose arrangement of the chapters, sometimes by substrate, other times according to reaction type or specific topics such as “bioorganic compounds”. The book is thus significantly less structured than comparable textbooks, but at the same time avoids mentioning complicated reactions at the beginning, which would inevitably be the case with a stricter organization according to substance classes. On the other hand, the reactions omitted in the early portion of the book appear later in a few chapters that seem somewhat busy as a result.

The book covers all major topics for a basic course, from orbitals, nomenclature, spectroscopy, and reactions to natural products and an introduction to medicinal chemistry. However, despite its large scope, it is only suitable for basic study or when repeating the fundamentals. The cogent descriptions of reaction types and exceptionally good illustrations serve their purpose well and make this a comprehensive text. However, this reviewer is convinced that this treatment is easier to work through than textbooks in which hundreds of reactions are presented with only brief explanations.

This book has a good focus on natural products and drug chemistry, so that it offers the important principles needed in more advanced study of biochemistry or medicinal chemistry. For relevance to today's life sciences industry, it is generally desirable for students to be exposed to interdisciplinary knowledge in their foundation courses. In these chapters, the level of detail corresponds rather more to the needs of beginning students.

“Organic Chemistry” by Paula Bruice is an outstanding textbook for beginning students, which explains the important fundamentals of biochemistry and medicinal chemistry. This book can lay the foundation for a successful course of studies, and its purchase is highly recommended.

Contents

An introduction to the study of organic chemistry
1. Electronic structure and bonding · acids and bases
2. An introduction to organic compounds nomenclature, physical properties, and representation of structure

Electrophilic addition reactions, stereochemistry, and electron delocalization
3. Alkenes: structure, nomenclature and an introduction to reactivity · thermodynamics and kinetics
4. The reactions of alkenes
5. Stereochemistry: the arrangement of atoms in space; the stereochemistry of addition reactions
6. The reactions of alkynes · an introduction to multistep synthesis
7. Delocalized electrons and their effect on stability, reactivity, and pka · more about molecular orbital theory

Substitution and elimination reactions
8. Substitution reactions of of alkyl halides
9. Elimination reactions of alkyl halides · competition between substitution and elimination
10. Reactions of alcohols, amines, ethers, expoxides, and sulfur-containing compounds · organometallic compounds
11. Radicals · reactions of alkanes

Identification of organic compounds
12. Mass spectrometry, infrared spectroscopy, and ultraviolet/visible spectroscopy
13. NMR spectroscopy

Aromatic compounds
14. Aromaticity · reactions of benzene
15. Reactions of substituted benzenes

Carbonyl compounds
16. Carbonyl compounds I: nucleophilic acyl substitution
17. Carbonyl compounds II
18. Carbonyl compounds III: reactions at the α-carbon

Oxidation-reduction reactions and amines
19. More about oxidation-reduction reactions
20. More about amines. heterocyclic compounds

Bioorganic compounds
21. Carbohydrates
22. Amino acids, peptides, and proteins
23. Catalysis
24. The organic mechanisms of the coenzymes
25. The chemistry of metabolism
26. Lipids
27. Nucleosides, nucleotides, and nucleic acids

Special topics in organic chemistry
28. Synthetic polymers
29. Pericyclic reactions
30. The organic chemistry of drugs: discovery and design

Organic Chemistry

Jonathan Clayden, Nick Geeves, Stuart Warren

Paperback, 1234 Pages
2nd Edition, 2012
ISBN: 978-0199270293
Oxford University Press

Description

A first and second year undergraduate organic chemistry textbook, specifically geared to British and European courses and courses offered in better schools in North America. The emphasis is on clarity and understanding, with very careful explanations of difficult concepts, many examples related to everyday life, and a fresh and student-friendly writing style.

Editorial Review

If there is a text book for organic chemistry, which I can recommend without restriction, then it is "Organic Chemistry" from the authors Clayden/Greeves/Warren/Wolters. There are several reasons for this:

The book accompanies the beginner in organic chemistry from the structure of the molecules, over NMR up to the topics for advanced, like heterocycles and asymmetrical synthesis. A typical arrangement of functional groups as seen in older text books does not occur. Thus, rather mechanisms and concepts of organic chemistry with rising difficulties are explained. Therefore it can be seen , that a certain mechanism (e.g. the addition to a carbonyl group) can be applied to different functional groups.

A large deficiency of comparable books are the given schemes, which mostly contain "R groups". In this regard, "Clayden" is very practice-related. Thus, in the chapter "acidity, basicity and pKa", the base instability of the Fmoc protective group is explained . Examples like the synthesis of the antibiotic ofloxacin are skillfully inserted later.

As very successful I call the marginal notes. Thus a mechanism is explained again in another kind, or you receive hints, referring to earlier or later chapters, where you can find more information about the topic. Marginal notes contain remarks like "The Favorskii mechanism want help you understand the Ramberg-Baecklund reaction... ". The book doesn´t lead you in temptation of stubborn memorization, but does promote interlaced thinking.

Interesting additions are, e.g. chapters about main group chemistry (S, B, Si...), "Organometallic Chemistry" and "The Chemistry of Life". Therefore the book is not only recommendable for lectures in organic chemistry, but also as a companion in biochemistry lectures.

Who "Clayden" possesses, has in lectures where alcohols, amines, carbonic acids and amides are strictly treated separately from each other, probably more or less to keep leafing back and forth and back again. However, this book has, compared with usual text books, to offer some pluses.

Beyond that, I recommend lecturers the acquisition of an "inspection copy". You should use this offer,
to promote organic knowledge in another way and to encourage interlaced thinking.

Contents

1 What is organic chemistry?
Organic Chemistry and this book
2 Organic structures
3 Determining organic structures
4 Structure of molecules
5 Organic reactions
6 Nucleophilic addition to the carbonyl group
7 Delocalization and conjugation
8 Acidity, basicity, and pKa
9 Using organometallic reagents to make C-C bonds
10 Conjugate addition
11 Proton nuclear magnetic resonance
12 Nucleophilic substitution at the carbonyl (C=O) group
13 Equilibria, rates, and mechanisms: summary of mechanistic principles
14 Nucleophilic substitution at C=O with loss of carbonyl oxygen
15 Review of spectroscopic methods
16 Stereochemistry
17 Nucleophilic substitution at saturated carbon
18 Conformational analysis
19 Elimination reactions
20 Electrophilic addition to alkenes
21 Formation and reactions of enols and enolates
22 Electrophilic aromatic substitution
23 Electrophilic alkenes
24 Chemoselectivity: selective reactions and protection
25 Synthesis in action
26 Alkylation of enolates
27 Reactions of enolates with aldehydes and ketones: the aldol reaction
28 Acylation at carbon
29 Conjugate addition of enolates
30 Retrosynthetic analysis
31 Controlling the geometry of double bonds
32 Determination of stereochemistry by spectroscopic
33 Stereoselective reactions of cyclic compounds
34 Diastereoselectivity
35 Pericyclic reactions 1: cycloadditions
36 Pericyclic reactions 2: sigmatropic and electrocyclic reactions
37 Rearrangements
38 Fragmentation
39 Radical reactions
40 Synthesis and reactions of carbenes
41 Determining reaction mechanisms
42 Saturated heterocycles and stereoelectronics
43 Aromatic heterocycles 1: structures and reactions
44 Aromatic heterocycles 2: synthesis
45 Asymmetric synthesis
46 Organo-main-group chemistry I: sulfur
47 Organo-main-group chemistry II: boron, silicon, and tin
48 Organometallic chemistry
49 The chemistry of life
50 Mechanisms in biological chemistry
51 Natural products
52 Polymerization
53 Organic chemistry today

Organic Mechanisms - Reactions, Stereochemistry and Synthesis

Reinhard Brückner

Hardcover, 636 Pages
First Edition, 2002
ISBN: 978-3-642-03650-7
Springer

Description

Organic Reactions · Stereochemistry · Modern Synthetic Methods is aimed at those who desire to learn organic chemistry through an approach that is facile to understand and easily committed to memory. Throughout the book fundamental and advanced reaction mechanisms are presented with meticulous precision. The systematic use of red "electron-pushing arrows" allows students to follow each transformation elementary step by elementary step. Mechanisms are not only presented in the traditional contexts of rate laws and substituent effects but, whenever possible, are illustrated using practical, useful and state-of-the-art reactions. The abundance of stereoselective reactions included in the treatise makes the reader familiar with key concepts of stereochemistry.

The fundamental topics of the book address the needs of upper-level undergraduate students, while its advanced sections are intended for graduate-level audiences. Accordingly, this book is an essential learning tool for students and a unique addition to the reference desk of practicing organic chemists, who as life-long learners desire to keep abreast of both fundamental and applied aspects of our science. In addition, it will well serve ambitious students in chemistry-related fields such as biochemistry, medicinal chemistry and pharmaceutical chemistry.

Editorial Review

Organic chemistry textbooks are generally aimed either at beginners or more advanced students. However, Reinhard Brückner’s “Advanced Organic Chemistry” is a work that can accommodate either undergraduate or graduate students.

The chapters are organized thematically, and contain sections that are targeted at both novice as well as more experienced students. The student working toward a first degree in chemistry can postpone study of those sections that are identified as advanced work, while the student pursuing an advanced degree can work through the entire text.

With its focus on reaction mechanisms, the Brückner text serves as an illustrative supplement to conventional textbooks, while it cannot replace them. The strengths of "Advanced Organic Chemistry" clearly lie in its very good explanations of mechanisms, the cleverly chosen examples (Brückner employs significantly fewer R-groups than other authors), and the literature citations for further reading.

For some of the mechanisms, such as SN1 and SN2, the examples are tabulated so that it is easy to recognize which is the relevant mechanism. The style of "Advanced Organic Chemistry" is generally engaging, and leads to a ready understanding, even of problematic chemical relationships.

Brückner is recommended as the resource to turn to when a supplementary treatment is needed.

Contents

Radical Substitution Reactions at the Saturated C Atom
Nucleophilic Substitution Reactions at the Saturated C Atom
Electrophilic Additions to the Olefinic C=C Double Bond
β-Eliminations
Substitution Reactions on Aromatic Compounds
Nucleophilic Substitution Reactions at the Carboxyl Carbon
Carboxylic Compounds, Nitriles, and Their Interconversion
Carbonic Acid Derivatives and Heterocumulenes and Their Interconversion
Additions of Heteroatom Nucleophiles to Carbonyl Compounds and Subsequent Reactions-Condensations of Heteroatom Nucleophiles with Carbonyl Compounds
Addition of Hydride Donors and of Organometallic Compounds to Carbonyl Compounds
Conversion of Phosphorus- or Sulfur-Stabilized C Nucleophiles with Carbonyl Compounds: Addition-Induced Condensations.
The Chemistry of Enols and Enamines
Chemistry of the Alkaline Earth Metal Enolates
Rearrangements
Thermal Cycloadditions
Transition Metal-Mediated Alkenylations, Arylations and Alkynylations
Oxidations and Reductions

Organic Reaction Mechanisms

M. Gomez Gallego, M. A. Sierra

Hardcover, 290 Pages
First Edition, 2004
ISBN: 3-540-00352-5
Springer, Berlin

Description

Organic Reaction Mechanisms shows readers how to interpret the experimental data obtained from an organic reaction, and specifically how an organic reaction mechanism can be considered or rejected based on the analysis of the experimental evidence. Whilst examining a series of selected examples of mechanisms, the text focuses on real cases and discusses them in detail. The examples are arranged to elucidate key aspects of organic reaction mechanisms. The authors employ all the types of information that the authors of the original work considered useful and necessary, including spectroscopic data, kinetic and thermodynamic data, isotopic labelling and organic reactivity. The book makes an excellent primer for advanced undergraduates in chemistry who are preparing for exams and is also useful for graduate students and instructors.

Editorial Review

Every organic chemist is familiar with the basic mechanisms: SN2, SN1, eliminations, aromatic substitutions... But there are reactions, where the product spectrum lets assume that the reactions take place by another, perhaps unexpected mechanism. Assumptions were set up and experiments with labeled compounds were done to find out about the kinetics of the reaction and the reaction mechanism.

These methods are described very detailed and alive in "Organic Reaction Mechanisms". Based on interesting examples from the current literature, findings, considerations and control experiments were explained and the most probable mechanism is then selected. The examples reach from the influence of lewis acids in the nucleophilic addition to carbonyles up to the esterification of a carbonic acid with dimethyl carbonate and DBU. Thus, they cover a large range of reactions and are arranged according to the rising degree of difficulty.

The ones who love organic chemistry, will devour the book like a crime film. Only very painstakingly work and logical conclusions lead to the correct mechanism. 40 cases became in "Organic Reaction Mechanisms" excitingly delineated. Because the solution is presented at the end of the current case, the reader is obliged to puzzle

Organic Synthesis - State of the Art 2003
2005

Douglass F. Taber

Hardcover, 216 Pages
First Edition, 2006
ISBN: 0-470-05331-3
Wiley-Interscience

Description

The first in a new series, Organic Synthesis: State of the Art 2003–2005 pulls together two years' worth of Taber's popular and highly-regarded column, and comprises a concise, extremely useful overview of current accomplishments in the field of organic synthesis. The 103 articles in this volume review the leading synthetic procedures developed over the last two years, discussing their significance and their applications. The more than 100 reactions covered in this First Volume of the series include:

  • Heterocycle Construction by Grubbs Metathesis
  • Enantioselective C-C Bond Construction
  • Organic Reactions in Ionic Liquids

Enhanced by author and subject-transformation indices, Organic Synthesis: State of the Art 2003–2005 offers chemists an effective, much-needed way to stay abreast of what's new and exciting in their field.

Editorial Review

Four years ago, Professor Taber contacted me to see whether I had any interest in publishing a weekly column he would write. At the time, the inquiry caught me by surprise, since the web project was nowhere near as elaborate as it is today. I believe that it was the publication of Douglass F. Taber’s "Highlights" that provided the initial impetus to invest further in original content. In this way, the contributions from Douglass played an essential catalytic role in accelerating the development of this project.

From my perspective, the “Highlights” are a good opportunity to glean information on really interesting reactions each week, and once the curiosity has been piqued one can investigate further by consulting the cited literature. The number of page views for these Highlights continues to increase, which is another indication of high interest by visitors to the site in having such short reviews published here. The numerous responses by readers have inspired us to continue producing this column, as have reviews such as that by Kilian Muniz, who wrote, “These days, when such an overwhelming amount of material is published, it is convenient to be able to access summarized information and gain a quick overview of a current topic.” (Angew. Chem. Int. Ed. 2004, 43, 2468. DOI).

Recently, Douglass decided to publish a first collection of these Highlights in book form, and found in Wiley a publisher who was enthusiastic about the idea. The book "Organic Synthesis - State of the Art 2003
2005" is the end result. Now it comes down to penning an unbiased review of this work, which is a bit of a challenge considering that all of the content has been published in this same site over the past four years. However, readers can now simply check for themselves whether or not to purchase "Organic Synthesis - State of the Art" by referring to Douglass F. Taber’s previous publications in our "Highlights".

To the price-conscious reader, the question of why to acquire the book naturally arises. The author provides the following answer to this question: "So, why this book, if the columns are already available free on the Web? First, there are a lot of them, 103 in this book. It is convenient having them all in one place. Too, there is an index of senior authors, and a subject/transformation index. Most important, this collection of columns, taken together, is an effective overview of the most important developments in organic synthesis over the two-year period."

I believe that anyone who reads the web edition on a weekly basis, and enjoys the topical exposure to the interesting reactions published there, should seriously consider purchasing the book. My hope for the author is that sales of this work will be brisk. For one thing, it will confirm the high level of interest in Douglass's work and in these Highlights; at the same time, it will also compensate the effort made each week to produce these columns, the free availability of which has already benefited many. I will be very pleased if we can successfully produce such chemistry content not only when it is freely accessible on the web, but also when available in book form, and I hope that we are able to carry along the content in both media as long as possible. You the readers can do your part!

Contents

1. Transition metal-mediated reactions in organic synthesis.
2. Biotransformations in organic synthesis.
3. Catalytic Enantioselective Synthesis.
4. Enantioselective Synthesis of Borrelidin.
5. Enantioselective Ring Construction.
6. New Routes to Heterocycles.
7. Total Synthesis of the Galbulimima Alkaloid GB 13.
8. Total Synthesis of Ingenol.
9. Best Synthetic Methods: Functional Group Transformations.
10. New Methods for Carbon-Carbon Bond Formation.
11. Mini-Review: Organic Reactions in Ionic Liquids.
12. Adventures in Polycyclic Ring Construction.
13. Synthesis of the Mesotricyclic Diterpenoids Jatrophatrione and Citlalitrione.
14. Best Synthetic Methods: Functional Group Transformations.
15. The Grubbs Reaction in Organic Synthesis.
16. C-N Ring-Forming Reactions by Transition Metal-Catalyzed Intramolecular Alkene Hydroamination.
17. Synthesis of (+)-Phomactin A.
18. Enzymes in Organic Synthesis.
19. Adventures in Polycarbocyclic Construction.
20. Construction of Enantiomerically-Pure Heterocycles.
21. Best Synthetic Methods: Functional Group Transformations.
22. Synthesis of (+)-4,5-Deoxyneodolabelline.
23. New Methods for Carbon-Carbon Bond Formation.
24. Strategies for Enantioselective Synthesis.
25. Preparation of Cyclic Amines.
26. Enantioselective Total Synthesis of (+)-Amphidinolide T1.
27. Stereocontrolled Construction of Carbacycles.
28. “Organometallic” Coupling without the Metal!
29. Preparation of Enantiomerically-Pure Building Blocks.
30. Synthesis of (-)-Strychnine.
31. Pd-Mediated Coupling in Organic Synthesis: Recent Milestones.
32. Enantioselective C-C Bond Construction: Part One of Three.
33. Enantioselective C-C Bond Construction: Part Two of Three.
34. Enantioselective C-C Bond Construction: Part Three of Three.
35. Synthesis of (-)-Podophyllotoxin.
36. The Grubbs Reaction in Organic Synthesis: Part One of Three.
37. The Grubbs Reaction in Organic Synthesis: Part Two of Three.
38. The Grubbs Reaction in Organic Synthesis: Part Three of Three.
39. Synthesis of Deacetoxyalcyonin Acetate.
40. Enantioselective Ring Construction: Part One of Two.
41. Enantioselective Ring Construction: Part Two of Two.
42. Alkyne Metathesis in Synthesis: Syntheses of (+)-Ferrugine and Anatoxin-α.
43. Catalytic Asymmetric Synthesis of Quinine and Quinidine.
44. Best Synthetic Methods: Oxidation and Reduction.
45. Best Synthetic Methods: Enantioselective Oxidation and Reduction.
46. Asymmetric Nucleophilic Epoxidation.
47. Asymmetric Synthesis of Nitrogen Heterocycles.
48. Synthesis of Amphidinolide T1.
49. Enantioselective C-C Bond Construction: Part One of Two.
50. Enantioselective C-C Bond Construction: Part Two of Two.
51. Advances in Nitrogen Protection and Deprotection.
52. Enantioselective Synthesis of (+)-Tricycloclavulone.
53. Best Methods for C-C Bond Construction: Part One of Three.
54. Best Methods for C-C Bond Construction: Part Two of Three.
55. Best Methods for C-C Bond Construction: Part Three of Three.
56. Formation of Aromatic-Amino and Aromatic-Carbon Bonds.
57. Synthesis of the Dendrobatid Alkaloid 251F.
58. Enantioselective Construction of Aldol Products: Part One of Two.
59. Enantioselective Construction of Aldol Products: Part Two of Two.
60. Enantioselective α-Functionalization of Carbonyl Compounds.
61. Synthesis of (-)-Hamigeran B.
62. Catalytic C-C Bond-Forming Reactions.
63. Rare Sugars are now Readily Available Chiral Pool Starting Materials.
64. Alkyne Metathesis in Organic Synthesis.
65. Total Synthesis of (±)-Sordaricin.
66. Ru-Mediated Intramolecular Alkene Metathesis: Improved Substrate and Catalyst Design.
67. Heterocycle Construction by Grubbs Metathesis.
68. Natural Product Synthesis using Grubbs Metathesis: Lasubine II, Ingenol, and Ophirin B.
69. Synthesis of (-)-Tetrodotoxin.
70. Diastereoselective and Enantioselective Construction of Aza- Heterocycles.
71. Diastereoselective and Enantioselective Construction of Cyclic Ethers.
72. Synthesis of Heterocyclic Natural Products: (-)-Ephedradine A, (-)-α-Tocopherol, (-)-Lepadin D and (-)-Phenserine.
73. Protection of N- and O-Functional Groups.
74. Synthesis of (-)-Norzoanthamine.
75. Best Synthetic Methods: C-C Bond Formation.
76. Enantioselective Construction of Single Stereogenic Centers.
77. Enantioselective Construction of Arrays of Stereogenic Centers.
78. Synthesis of (-)-Brasilenyne.
79. Best Synthetic Methods: Functional Group Transformations.
80. Enantioselective Construction of Oxygenated and Halogenated Secondary Centers.
81. Enantioselective Construction of Aminated Secondary Centers.
82. Enantioselective Synthesis of the Polyene Antibiotic Aglycone Rimocidinolide Methyl Ester.
83. Enantioselective Transformations of Prochiral Rings.
84. Michael Reactions for Enantioselective Ring Construction.
85. Enantioselective Ring Construction by Intramolecular C-H Insertion and by Cycloaddition.
86. Best Synthetic Methods: Construction of Aromatic and Heteroaromatic Rings.
87. Enantioselective Synthesis of (+)-Epoxomycin.
88. Best Synthetic Methods: Functionalization of Aromatic and Heteroaromatic Rings.
89. Best Synthetic Methods: Oxidation.
90. Enantioselective Allylic Carbon-Carbon Bond Construction.
91. Synthesis of (+)-Cyanthawigin U.
92. Catalysts and Strategies for Alkene Metathesis.
93. N-Heterocycle Construction by Alkene Metathesis.
94. O-Heterocyclic Construction by Alkene Metathesis.
95. Alkene Metathesis in total synthesis: Valienamine, Agelastatin and Tonantzitlolone.
96. Total Synthesis of the Tetracyclines.
97. Enantioselective Construction of N-Heterocycles.
98. Stereocontrolled Construction of Cyclic Ethers.
99. Synthesis of the Proteosome Inhibitors Salinosporamide A, Omuralide and Lactacystin.
100. Synthesis of (-)-Sordaricin.
101. Recent Advances in Carbocyclic Ketone Construction.
102. Stereoselective Construction of Carbocyclic Rings.
103. Asymmetric Transformation of Prochiral Carbocyclic Rings.

Organic Synthesis with Enzymes in Non-Aqueous Media

Giacomo Carrea, Sergio Riva

Hardcover, 328 Pages
First Edition, 2008
ISBN: 3-527-31846-1
Wiley-VCH

Description

losing a gap in the literature, this comprehensive book examines and discusses different non-aqueous systems from organic solvents to ionic liquids for synthetic applications, thus opening the door to new successful methods for biocatalytic reactions. It gathers into one handy source the information otherwise widely spread throughout the literature, combining useful background information with a number of synthetic examples, including industrial scale processes for pharmaceutical and fine chemicals.

Extremely well structured, the text introduces the fundamentals of non-aqueous enzymology, before going on to new reaction media and synthetic applications using hydrolases and non-hydrolytic enzymes.

The one-stop reference for everyone working in this hot field.

Editorial Review

Enzymes frequently offer unique selectivity in reactions with appropriate substrates. In addition to examples of enantioselective reactions, surprising chemoselectivity and regioselectivity have been reported in the transformations of multifunctional molecules. However, a disadvantage is that there are limitations to enzymes functioning in organic solvents, since both enzymes and their natural biological substrates are more water soluble than the molecules that come up in the everyday life of a chemist.

Several interesting techniques are available that permit enzymes to function in organic media with comparable activity and selectivity to that found under physiological conditions, and these are described in the first portion of the present book. To provide a basic foundation, explanations are provided for a number of effects that influence enzyme function. Although there is some overlap between the chapters, these fundamental principles definitely make worthwhile reading, and are accessible to advanced students even as expressed in the mathematical symbolic expressions that are employed in a few of the chapters. In the later portions as well, where a large number of reaction examples are encountered, there are some chapters with a large proportion of specific formulas that should appeal primarily to engineers. Thus, for example, biphasic transformations are described in detail using numerous mathematical formulas, also to the extent that they relate to industrial scale processes, while at the same time other chapters are limited to reactions from the current literature.

This monograph combines a commendable introduction with a multitude of examples of the reactions of important functional groups, as well as technical chapters that are quite good albeit heavily laden with formulas. All of these make the book attractive to anyone with an interest in enzymes, or who is looking for alternatives or concrete information concerning the scale-up of a reaction, or who needs tips on the use of enzymes.

Contents

Part One Biocatalysis in Neat Organic Solvents – Fundamentals.

1 Fundamentals of Biocatalysis in Neat Organic Solvents (Patrick Adlercreutz).

1.1 Introduction.

1.2 Effects of Water on Biocatalytic Reactions.

1.3 Solvent Effects.

1.4 Effects on Equilibria.

1.5 Effects of pH in Organic Solvents.

1.6 Concluding Remarks.

2 Effects of Organic Solvents on Enzyme Selectivity (Jaap A. Jongejan).

2.1 Introduction.

2.2 Enzyme Enantioselectivity.

2.3 Effects of Organic Solvents on the E-value.

2.4 Possible Causes of the Complexity of Solvent Effects on E.

2.5 The Accuracy of E-value Determinations.

2.6 Kinetic and Thermodynamic Analysis of the Specifi city Constants.

2.7 Solvents Effects on Non-Hydrolytic Enzymes.

2.8 Major Achievements.

2.9 Concluding Remarks.

3 Activating Enzymes for Use in Organic Solvents (Anne L. Serdakowski, Jonathan S. Dordick).

3.1 Introduction.

3.2 Water – A Unique and Necessary Solvent for Enzymatic Catalysis.

3.3 Enzyme Activation in Nonaqueous Media.

3.4 Salt-Activated Enzymes.

3.5 Conclusions.

Part Two Biocatalysis in Neat Organic Solvents – Synthetic Applications 4 Exploiting Enantioselectivity of Hydrolases in Organic Solvents (Hans-Erik Högberg).

4.1 Introduction.

4.2 Enantioselective Reactions in Organic Solvents.

4.3 Summary and Outlook.

5 Chemoenzymatic Deracemization Processes (Belén Martín-Matute and Jan-E. Bäckvall).

5.1 Introduction.

5.2 Dynamic Kinetic Resolution.

5.3 Cyclic Deracemizations.

5.4 Concluding Remarks.

6 Exploiting Enzyme Chemoselectivity and Regioselectivity (Sergio Riva).

6.1 Introduction.

6.2 Chemoselectivity of Hydrolases.

6.3 Regioselectivity of Hydrolases.

6.4 Closing remarks.

7 Industrial-Scale Applications of Enzymes in Non-Aqueous Solvents (David Pollard and Birgit Kosjek).

7.1 Introduction.

7.2 Ester Synthesis by Esterifi cation.

7.3 Resolution of Racemic Alcohols.

7.4 Kinetic Resolution of Racemic Amines.

7.5 Resolution of Amino Alcohols and Methyl Ethers.

7.6 Resolution of an Ester.

7.7 Desymmetrization by Transesterifi cation.

7.8 Regioselective Acylation.

7.9 Asymmetric Ring Opening of Racemic Azlactone.

7.10 Cyanohydrin Formation.

7.11 Outlook.

Part Three Biocatalysis in Biphasic and New Reaction Media.

8 Biocatalysis in Biphasic Systems: General (Pedro Fernandes and Joaquim M. S. Cabral).

8.1 Introduction.

8.2 Organic-Aqueous Biphasic Systems: General Considerations.

8.3 Classifi cation of the Systems: Macro- and Microheterogeneous Systems.

8.4 Mechanisms of Enzyme Inactivation.

8.5 Approaches to Protection of the Enzyme.

8.6 Solvent Selection.

8.7 Operational Parameters.

8.8 Reactor Types.

8.9 Downstream Processing.

8.10 Recent Applications.

8.11 Conclusions.

Acknowledgments.

9 Biocatalysis in Biphasic Systems: Oxynitrilases (Manuela Avi and Herfried Griengl).

9.1 Introduction.

9.2 Biphasic Systems.

9.3 Conclusion.

10 Ionic Liquids as Media for Enzymatic Transformations (Roger A. Sheldon and Fred van Rantwijk).

10.1 Introduction.

10.2 Solvent Properties of Ionic Liquids.

10.3 Enzymes in Ionic Liquids.

10.4 Enzymes in Nearly Anhydrous Ionic Liquids.

10.5 Stability of Enzymes in Nearly Anhydrous Ionic Liquids.

10.6 Whole-Cell Biotransformations in Ionic Liquids.

10.7 Biotransformations in Ionic Liquid Media.

10.8 Downstream Processing.

10.9 Conclusions.

11 Solid/Gas Biocatalysis (Isabelle Goubet, Marianne Graber, Sylvain Lamare, Thierry Maugard and Marie-Dominique Legoy).

11.1 Introduction.

11.2 Operating Solid/Gas Systems.

11.3 Infl uence of Operational Parameters on the Dehalogenase Activity of Whole Dehydrated Cells.

11.4 Conclusion.

12 Biocatalysis with Undissolved Solid Substrates and Products (Alessandra Basso, Sara Cantone, Cynthia Ebert, Peter J. Halling and Lucia Gardossi).

12.1 Introduction.

12.2 The Reaction System: Classifi cation.

12.3 Theory.

12.4 Factors Affecting the Reactions in the Presence of Undissolved Substrates/Products.

12.5 Precipitation-Driven Synthesis of Peptides.

12.6 Precipitation-Driven Synthesis of Esters and Surfactants.

12.7 The Synthesis of β-Lactam Antibiotics in the Presence of Undissolved Substrates.

12.8 Conclusion.

Pericyclic Reactions - A Textbook

Sethuraman Sankararaman

Softcover, 418 Pages
First Edition, 2005
ISBN: 3-527-31439-3
Wiley-VCH, Weinheim

Description

This long awaited textbook presents Diels-Alder reactions, electrocyclic reactions, sigmatropic rearrangements plus many more topics in a highly didactic way, with both classical and new examples explained in detail.

With a foreword by Nobel Laureate Roald Hoffmann.

Editorial Review

Reactions in which rings are formed or that involve passage through a cyclic transition state, where a concerted shift of electrons plays a role, can be explained with just a few rules. Is the reaction thermally allowed or forbidden, and most of all, what configuration will the final product have? Answers can be had easily, with just some knowledge. However, these questions are extremely important in view of the impact of such reactions on the construction of interesting intermediates. As evidenced by some recent transformations in natural product synthesis alone, the potential of these reactions is so broad that the topic can only be covered in a superficial and unsatisfactory manner in textbooks that are devoted to a general treatment of organic chemistry. Thus, students who have difficulties with molecular orbital diagrams or in understanding the associated terminology and rules, or who wish to delve further into the subject for a special topics course, will want to consult a more in-depth treatment.

The book “Pericyclic Reactions - A Textbook” meets the expectations for just such a work. Only a little basic knowledge is necessary for the reader to follow the material. The author has made an effort to accompany all explanations with relatively simple schemes that clarify and support the text with minimal digression. A further bonus is the presentation of numerous specific transformations, which exemplify for the reader the enormous range of application for pericyclic reactions. The chapters are well-structured, with an introduction that is followed by a few sample reactions and cogent explanations.

The fundamentals of this subject are clarified in detail in this monograph, while it also offers many additional pointers and reactions that would disrupt the flow in a conventional textbook. Though its somewhat modest appearance belies the work’s compelling value, this is a substantial contribution to the field that is well worth the price. “Pericyclic Reactions - A Textbook” is recommended for everyone with an abiding interest in this topic.

Contents

Molecular Orbitals and Their Symmetry
Electrocyclic Reactions
Cycloaddition Reactions
Sigmatropic Rearrangements
Chelotropic, Group Transfer and Ene Reactions
Special Topics
Index

Reactions and Syntheses
in the Organic Chemistry Laboratory

Lutz F. Tietze, Theophil Eicher, Ulf Diederichsen, Andreas Speicher

Softcover, 598 Pages
1st Edition, 2007
ISBN: 978-3-527-31223-8
Wiley - VCH

Description

Presenting a broad spectrum of modern total synthesis of natural products, pharmaceuticals, heterocycles, C-C bonding and biochemical reactions, this practical textbook readily guides readers to the necessary information. A list of keywords in each chapter and numerous tables summarize the contents, resulting in an excellent overview.

Written with graduates in organic chemistry in mind, this is equally valuable for students and lecturers in chemistry, organic chemists, as well as lab technicians and chemists in industry.

Editorial Review

"Reactions and Syntheses" is an advanced textbook with concrete procedures that links theory together with practical syntheses. The individual chapters and concrete procedures are introduced with outstandingly crafted theoretical explanations. The book describes advanced organic chemistry using interesting examples, specifically natural products and drugs, the preparations of which are illustrated together with a retrosynthetic analysis and alternative synthesis routes. The important steps in the synthesis are thus also described from the mechanistic perspective, so that reading the book helps to enhance the knowledge imparted.

The syntheses themselves are described in a practicable and accurate manner; for example, a number of passages contain warnings and tips for the use of specific chemicals. Since a broad range of specialized subjects are covered, while modern synthesis chemistry has also been given its due, we have here an advanced textbook that will cover several interesting synthetic options with concrete procedures. Since the focus is on both the target molecules and multi-step syntheses, there is relatively less attention given to individual functional groups and their transformations. This isn’t really a disadvantage; instead of “esterification” followed by a list of 10 examples, the theory is treated in depth with respect to a specific molecule, the synthesis of which is described over from one to five or six steps. Thus, the book is more a remarkable textbook for advanced students than a standard reference work for synthesis chemistry to be consulted on a daily basis by professionals in a synthesis laboratory.

On the one hand, "Reactions and Syntheses" contains all of the information necessary to carry out experiments, so that students don't have the opportunity to do the preliminary work such as independent literature search and stoichiometric calculations on their own before running the actual reactions. On the other hand, the theory and concrete examples are presented in such a way that students benefit many times over in that they can both draw connections with the conceptual knowledge and readily gain experience with specific syntheses. Instructors should consider all of these features as they evaluate the book for use in a laboratory course. In any case, acquiring this book is worthwhile for students, who will not only obtain a practical guide, but also an organic chemistry textbook that will help them to solidify their knowledge of the subject.

Contents

C-C BOND FORMATION
Nucleophilic Addition to Aldehydes, Ketones, Carboxylic Acid Derivatives (Esters, Anhydrides) and Alpha,Beta-unsaturated Carbonyl Compounds;
Carbonyl Olefination
Alkylation of Aldehydes/
Ketones, Carboxylic Acids and Beta-dicarbonyl Compounds
Reactions of the Aldol and Mannich Type
Electrophilic and Nucleophilic Acylation
Reactions of Alkenes via Carbenium Ions
Transition-metal Mediated Reactions
Pericyclic Reactions
Radical Reactions
OXIDATION AND REDUCTION
Epoxidation of C=C Bonds
Dihydroxylation of C=C Bonds
Oxidation of Alcohols to Carbonyl Compounds
Enantioselective Reduction of Ketones
HETEROCYCLIC COMPOUNDS
Three- and Four-membered Heterocycle
Five-membered Heterocycles
Six-membered Heterocycles
Condensed Heterocycles
Other Heterocyclic Systems, Heterocyclic Dyes
SELECTED NATURAL PRODUCTS
Amino Acids and Peptides
Alkaloids
Terpenoids, Steroids
Carbohydrates

Stereochemie - Grundbegriffe

Karl-Heinz Hellwich

Paperback, 102 Seiten
1. Auflage, 2002
ISBN: 3-540-42347-8
Springer, Berlin

>> Übungen zur Stereochemie

Beschreibung

Stereochemie - Grundbegriffe richtet sich an Studenten, Lehrende und praktizierende Wissenschaftler der Chemie, Biochemie, Pharmazie, Medizin und Biologie, die sich mit dem Phänomen der Chiralität befassen. Neben einer genauen Formeldarstellung ist eine klare und eindeutige Terminologie zur Beschreibung der dreidimensionalen Strukturen und der daraus resultierenden Konsequenzen für Reaktionen oder Wirkstoff-Rezeptor-Wechselwirkungen unerläßlich. Das gilt umsomehr im zunehmenden interdisziplinären Austausch. Das vorliegende Buch eklärt alle wichtigen Begriffe der Stereochemie in lexikalischer Form, greift dabei widersprüchliche Terminologie auf und weist auf deren richtige Verwendung hin.

Meinung der Redaktion

Stereochemie ist eines der Gebiete, das einem Teil der Studienanfänger nicht liegt. Hier gilt es, zu üben und zu verstehen. Karl-Heinz Hellwich - ein offizielles Mitglied der IUPAC-Kommission für Nomenklatur der Organischen Chemie - hat zwei Bücher geschrieben, welche wahrlich eine Hilfe sind: "Stereochemie - Grundbegriffe" und "Übungen zur Stereochemie".

"Stereochemie - Grundbegriffe" ist dank seines lexikalischen Aufbaus vor allem bei unklaren Begriffen nützlich; aber auch das Lesen macht Freude. Das Buch hilft, Stereochemie schneller zu vermitteln als dies nur in einer Vorlesung oder mit Hilfe eines Organik-Lehrbuches möglich wäre. Die Erklärungen sind leicht verständlich, die wichtigsten Begriffe sind enthalten und man kann sich sicher sein, dass der Autor den Empfehlungen der IUPAC folgt. Spezial-Fälle, welche nicht mehr trivial beschrieben werden können, werden zudem durch sehr gute Beispiele erläutert. Auf dieses Wissen wird man im Berufsleben gerne wieder zurückgreifen.

Structure and Reactivity in Organic Chemistry

Mark G. Moloney

Softcover, 306 Pages
First Edition, 2008
ISBN: 978-1-4051-1451-6
Wiley-Blackwell

Description

The jump from an understanding of organic chemistry at lower undergraduate level to that required at postgraduate level or in industry can be difficult. Many advanced textbooks contain a level of detail which can obscure the essential mechanistic framework that unites the huge range of facts of organic chemistry. Understanding this underlying order is essential in any advanced study or application of organic chemistry. Structure and Reactivity in Organic Chemistry aims to bridge that gap.

The text opens with a short overview of the way chemists understand chemical structure, and how that understanding is essential in developing a good knowledge of chemical reactivity and mechanism. The remainder of the text presents a mechanistic classification of modern organic chemistry, developed in the context of synthetic organic chemistry and exemplified by reference to stereoselective synthesis and protecting group chemistry. This approach is intended to illustrate the importance and value of a good grasp of organic reaction mechanisms, which is a prerequisite for a broader understanding of organic chemistry.

Written by an expert educator with a sound understanding of the needs of different audiences, the subject is presented with clarity and precision, and in a highly practical manner. It is relevant to undergraduates, postgraduates and industrial organic chemists.

Editorial Review

At first glance, Mark G. Moloney's book appears quite compact. Nevertheless, the author succeeds in conveying important fundamentals within this limited space, for example concerning molecular structure (AO, MO), the structure of organic compounds (isomers) and reactivity (thermodynamics and kinetics). Each individual chapter also contains extended commentaries that appeal to advanced students, which makes the chapter on specific mechanisms (e.g., nucleophilic substitution) especially valuable. The introduction, mechanistic details and good, concrete examples found here provide students with a greater depth of knowledge.

What will scare off beginners works quite well for the advanced students, and that is a comprehensive analysis from the simple fundamentals to complex examples within a single chapter, which facilitates rapid learning and memorization. The consistently good illustrations (e.g., the MOs in cycloadditions) and a writing style that is easy to understand make "Structure and Reactivity in Organic Chemistry" a modern textbook that one is eager to pick up for reviewing the fundamentals. The book is ideal in this respect, for when one wants to revisit the most important material once more before an exam; because of its coverage, it can’t replace an actual set of lecture notes or the primary textbook, but supplements them nicely!

Contents

1. Bonding
2. Structure
3. Reactivity
4. Intermediates
5. Acidity and Basicity
6. Nucleophilic Substitution
7. Addition Reactions
8. Elimination Reactions
9. Aromatic Substitution
10. Sequential Addition and Elimination Reactions
11. Radical Reactions
12. Ligand Coupling Reactions
13. Pericyclic Reactions

Superelectrophiles and Their Chemistry

George A. Olah, Douglas A. Klumpp

Hardcover, 301 Pages
First Edition, 2007
ISBN: 978-0-470-04961-7
Wiley

Description

Superelectrophiles and Their Chemistry contains, for the first-time, a discussion of the basics of this emerging field of organic chemistry, alongside tools to help the reader apply the chemistry. Specific tools include an evaluation of the ways to increase the strength of electrophiles, the classification of superelectrophiles, the solvation issues, a review of methods for studying superelectrophilicity, with details of the superelectrophiles that have been identified and studied. Additional information includes substituent effects in activation of superelectrophiles, and solvation in chemical reactions, as well as an insightful look into future applications.

Editorial Review

Olah and Klumpp have produced a book on the subject of Superelectrophiles and Their Chemistry, which deals in detail with polycationic electrophiles, their generation, properties and reactions. This area is extremely fascinating, since superelectrophiles undergo reaction with extremely weak nucleophiles, and thus the scope of chemical possibilities is greatly expanded.

The theory is explained at a level that can be readily understood by advanced students. The book will have some surprising moments, in this reviewer’s opinion, since some of the models and reactions lie far outside the chemical and physical possibilities that are explained in normal textbooks. Thus, Olah and Klumpp offer up a storehouse of new knowledge. Through a new understanding of some of these reactions, which are carried out in the normal course of laboratory operation, readers can see them through new eyes. These readers will benefit greatly, since the book contains a multitude of practical tips that can be applied in their own reactions.

Contents

1. General Aspects.
2. Study of Superelectrophiles.
3. Generating Superelectrophiles.
4. Gitonic Geminal Superelectrophiles.
5. Gitonic Vicinal Superelectrophiles.
6. Gitonic 1,3-Superelectrophiles.
7. Distonic Superelectrophiles.
8. Significance and Outlook.

The Art of Writing Reasonable Organic Reaction Mechanisms

Robert B. Grossman

Hardcover, 355 Pages
2nd Edition - 2003
ISBN: 0-387-95468-6
Springer, Berlin

Description

Intended for students of intermediate organic chemistry, this text shows how to write a reasonable mechanism for an organic chemical transformation. The discussion is organized by types of mechanisms and the conditions under which the reaction is executed, rather than by the overall reaction as is the case in most textbooks. The treatment emphasizes unifying principles, showing how common mechanisms link seemingly disparate reactions. Each chapter discusses common mechanistic pathways and suggests practical tips for drawing them. Worked problems are included in the discussion of each mechanism.

Editorial Review

One's approach to reaction mechanisms is a matter of preference. Students can either employ the underlying mechanistic principles in their analysis, or get around the problem of solving the Gordian knot by painstakingly committing the mechanism for every single (name) reaction in the repertoire to memory.

In principle, most mechanisms are derived from a basis set of fundamental steps. These fundamentals must be learned, applied, and practiced. Only then will one be in a position to rationalize complex transformations in mechanistic terms. Once these skills are mastered, it is a simple matter to sketch out a mechanistic pathway for a given set of reactants and products within a short while.

Grossman has succeeded in explaining these fundamentals in detail in an easily accessible monograph. He also comments on several common pitfalls and mistakes. Readers can reinforce their incipient skills with practical illustrations, and are challenged throughout with complicated examples. The solutions to these problems are available on the internet.

With the basic knowledge from an introductory course and a textbook at the ready, the present text offers additional lucid explanations and ideal opportunities for practice. This work will thus be indispensable for students who are interested in mechanisms, or who wish to gain additional perspective. This reviewer is certain that reading Grossman's book will help avoid making errors on exams! This is despite, and perhaps because of, the fact that its focus is on the underlying fundamental steps of mechanisms.

Contents

1 The Basics. 2 Polar Reactions under Basic Conditions. 3 Polar Reactions under Acidic Conditions. 4 Pericyclic Reactions. 5 Free-Radical Reactions. 6 Transition-Metal-Mediated and -Catalyzed Reactions. 7 Mixed-Mechanism Problems.

Wörterbuch der Chemie - Dictionary of Chemistry

Wörterbuch der Chemie - Dictionary of Chemistry
Antonin Kucera

Hardcover, 735 Pages
First Edition, 1 February 1997
ISBN: 3-87097-172-X
Brandstetter

Beschreibung

Kompakt, handlich und auf dem aktuellen Stand der Forschung und Terminologie: die Chemie-Wörterbücher von Antonín Kucera sind professionelle Nachschlagewerke für Chemiker, Laboranten, Studenten und Übersetzer.
Der Autor, der auf eine jahrzehntelange Erfahrung als Fachlexikograf und Fachübersetzer zurückgreifen kann, ist Garant für die bekannt hohe Qualität der Kucera-Bände.
Die Einträge wurden aus einschlägigen Monografien, Fachenzyklopädien und -zeitschriften zusammengetragen. Die Darstellung folgt dem bewährten Aufbau der anderen Wörterbücher desselben Autors:
- zahlreiche Kurzerläuterungen und Hinweise zur besseren sachlichen Einordnung der Fachbegriffe
- oft zusätzliche Angabe, welchem Teil- oder Anwendungsgebiet der Chemie ein Terminus angehört
- konsequente und konsistente Ausarbeitung der Synonymik und der Verweise
- klare Bedeutungsunterscheidung bei mehrdeutigen Begriffen.

Editorial Review

The present dictionary convinces through its handiness and clarity, and very importantly: by the selection of the words (56'000). Therefore, we could translate some English language citations easy into German. The book offers, however, more than the exclusive translation of a term: short explanations are given, so that complicated terms are understood fast. The explanations were only present in German (in the English and in the German-language part), which probably diminishes the value of the book a little for people from the English speaking world. Even though, the dictionary is worth a recommendation!

People who are not so powerful in the German language, have probably to fall back on the combination of a conventional dictionary and "Kucera". And those who have to translate complicated explanations of reaction mechanisms, will probably discover one or two words which are missing in the dictionary. However the dictionary creates clarity, with the multiplicity of the unclear terms from chemistry, and helps particularly with fast finding of appropriate German expressions.

Wörterbuch Labor - Laboratory Dictionary
Deutsch-Englisch - English-German

Theodor C.H. Cole

Hardcover, 453 Pages
2nd Edition, 2009
ISBN: 978-3-540-88579-5
Springer

Beschreibung

Das Labor ist Ausgangspunkt für die medizinische, pharmazeutische, chemische und biowissenschaftliche Forschung. Fachwissenschaftliches Englisch ist heute im Labor Voraussetzung für effiziente Kommunikation und erfolgreiches Arbeiten. Die entsprechenden Bezeichnungen von Laborausstattung, Geräten, Methoden und Technologie sollten genauso beherrscht werden wie die von Chemikalien und der sicherheitsrelevanten Terminologie. Das Wörterbuch enthält einen Grundwortschatz mit 12.000 Begriffen in jeder Sprachrichtung (Deutsch – Englisch), der dem Benutzer das Leben, Überleben und Arbeiten im Labor erleichtert. Nützlich ist das Wörterbuch für das Verständnis von Handbüchern, Katalogen, Gebrauchs- und Bedienungsanweisungen die bei Laborgeräten mitgeliefert werden, ebenso wie für das Lesen und Verfassen von Publikationen.

Description

Laboratories are the source of all medical, pharmaceutical, chemical, and bioscientific research. Scientific English in the laboratory is a prerequisite for efficient communication and successful work. The corresponding terminology for lab facilities, equipment, tools, methods and technology is of equal importance as that of chemicals and safety-relevant issues. The Laboratory Dictionary contains some 12,000 terms in both languages (German – English) that are essential for living, surviving, and working in the lab. The Laboratory Dictionary will prove itself useful in working with manuals, catalogs, and operation instructions delivered with laboratory equipment as much as for reading and writing of scientific publications.

Review by Matthew Schlecht (Word Alchemy)

For at least two centuries prior to the emergence of modern global and multinational business interests, the fields of science and medicine already spanned the globe regardless of national or continental borders. Practitioners would commonly gain additional training in the laboratories and clinics of a different country, and often in a different language. This robust tradition continues to the present day, although the development of new, cross-disciplinary specializations and the explosion in terminology and jargon have elevated the language barrier to be overcome in such positions.

No one in these fields will question the need for up-to-date technical glossaries such as the “Wörterbuch Labor/Laboratory Dictionary”, which aims to ease the German-English linguistic confusion in the fields of biochemistry, biotechnology, medicine, chemistry and chemical engineering. To get a picky point out of the way at the outset, this is a glossary and not a dictionary, as no real definitions are provided. This work is written primarily for the German-speaking professional who is working in an American facility, and may find terms such as ‘flea stirrer’, ‘cotton pledget’ or ‘falling film’ somewhat opaque. However, this terminology resource works well in both directions, and will also help the Anglophone professional struggling with ‘Schiebefenster’, or puzzling over the difference between ‘Hydratation’ and ‘Hydrierung’.

To be sure, much of the world’s technical and medical vocabulary has undergone homogenization, and cognate English is pervading usage in Europe (and Asia), even where the mother tongue has perfectly good equivalents. While ‘Flash-Chromatographie’ and ‘Western-Blot’ may have dubious parentage in German, they are now registered imports and unlikely to change. However, the differences still far outweigh the similarities, and tools such as this glossary still play an important role in the technical workplace.

One such feature is to redirect the unwary away from “false friends”, by distinguishing ‘Sonde/probe’ from ‘Probe/test or assay’. Another is to document different meanings in different contexts, which this glossary does well - for example, ‘ätzen’ is glossed here as ‘to cauterize’ in a medical context, ‘to etch’ in a metallurgical/technical context, and ‘to eat into, to corrode’ in a chemical context. More of these contextual nuances would be welcome, but the current coverage is quite good. Often, both the English loanword into German as well as the traditional German version are referenced, e.g. ‘herbicide’ is glossed as both ‘Herbizid’ and as ‘Unkrautvernichtungsmittel’.

A strength of this author’s format is the collection of thematically related terms under a main keyword or root word, in addition to their alphabetic listings. Thus, the types of chromatography, the types of condensers, the types of reactors, the types of glass, etc., are all gathered together for comparison. This greatly facilitates the inevitable guesswork where an exact term cannot be pinned down at first.

Any work of this type will have limitations, in order to balance the enormous lexical content of these technical fields against a workable size (and cost) of the book; the limitations present in this resource should be acceptable to most readers. The emphasis is on American English, and the corresponding British alternates are glossed only occasionally. The coverage of polymers, even as they relate to the stated technical scope (e.g. Merrifield resin), is sparse. Likewise, the treatment of molecular structure and computational modeling terms (e.g., ‘solvent accessible surface’) is also limited. One improvement that would not be too cumbersome would be to include an index of the common abbreviations used for the contained terms. Although there will always be some favorites missing, it would be gratifying if a future edition were to include such terms as ‘brine’, ‘fish’ (the insoluble bits inadvertently entering a reaction mixture and adding significant weight to a microscale reaction or crystallization after filtration of the solid product), or ‘heat kick’.

However, some of the limitations are really strengths. Of those covered, the medical field is given shorter shrift, which is realistic given the existence of numerous other glossaries that focus exclusively on this area, and with which it makes no sense to compete. Thankfully, this work does not try to be a chemical name index, although many generic and nonsystematic names are covered (e.g., ‘Gelbbrensäure’, ‘Epsom salts’). Many terms that are virtually or exactly identical in the two languages are not included, such as ‘Tetrahydrofuran/tetrahydrofuran’. These exclusions are well-advised as a way to conserve space.

In summary, the author has prepared an valuable resource that fills an important need for researchers, technicians, and even for technical translators. The excellent content and coverage, together with the reasonable price, make it strongly recommended to anyone whose work and research collaborations must bridge the German-English language barrier, and for every research group where cross-lingual communication is an everyday event.

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