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Science of Synthesis: Water in Organic Synthesis

, Thieme

Shu Kobayashi

Softcover, 960 Pages
First Edition, 2012
ISBN: 978-3131693518
Thieme

Description

"Water in Organic Synthesis" is essential for the organic chemist in helping gain a thorough appreciation of the latest and most reliable available methods for using water in organic synthesis. It illustrates how water can often be a viable and green solvent in the laboratory and provides a detailed introduction to the subject: background information, evaluated methods, practical applications, industrial applications, special techniques, and an overview of the latest trends. The reference work also helps in inspiring chemists worldwide to find new approaches and techniques for the application of water in organic synthesis.

Editorial Review

All chemists agree that some of their synthetic methods must be made greener. Reagents that are harmful to the environment, toxic, or hazardous should - whenever possible - be replaced with non-hazardous alternatives. Given the quantities involved, switching from organic solvents to water would seem to be a high priority, but this is often impossible due to the specific properties of water. There is clearly a great deal of skepticism that some reactions, well known for centuries to run only under water-free conditions, could be completely re-invented.

Certainly, the search for Lewis acids that are also catalytically active in aqueous solution has met with substantial success. Meanwhile, it is known that some cycloadditions are actually accelerated due to hydrophobic effects. While the use of water in this way might have seemed absurd in the past, more attention is now being focused on employing it as an alternative solvent since along with it being a green reaction procedure input, it also enables some faster and more selective transformations. Thus, for such a topic, it is not only necessary to list the current possibilities but also to convey the basic principles and identify perspectives for speeding up research and development. By these measures, the present work is a success from beginning to end, with some truly excellent chapters.

The middle section covers some frequently used bond formations, including thousands of interesting reactions from the recent literature. Not only are many additional fundamentals presented, one encounters several reactions are that find frequent application in the lab. A significant plus is that numerous concrete synthetic procedures are available, so the initial experiments could be begun using only this installment of the "Science of Synthesis". The chapters by different authors are impressive not only in their careful and uniform design, but also in details such as the elegant mechanisms or the precautions, which bespeaks either very clear style guidelines or extensive revision by the publisher.

With its well-designed and consistent reference works, the "Science of Synthesis" series offers greater value than other multi-author works in which the quality of chapters varies widely. Worth mentioning is the unique index, which pairs the keyword with a context excerpt in which the keyword appears. "Water in Organic Synthesis" is comparable to the best other books in this series, and offers a detailed portrait of a fascinating, multi-faceted research area that is richly endowed with well-developed and interesting reactions..

Contents

1 Introduction - S. Kobayashi
2 Structure and Properties of Water - S. Otto and J. B. F. N. Engberts
3 Aqueous Media: Reactions of C-C Multiple Bonds

3.1 Asymmetric Oxidation Reactions: Sulfoxidation, Epoxidation, Dihydroxylation, and Aminohydroxylation - T. Katsuki
3.2 Hydrogenation of Alkenes, Alkynes, Arenes, and Hetarenes - F. Joó
3.3 Hydroformylation and Related Reactions - L. T. Mika and I. T. Horváth
3.4 Conjugate Addition Reactions - N. Mase
3.5 Cyclopropanation Reactions - G. Simonneaux, P. Le Maux, and S. Chevance
3.6 Metathesis Reactions - C. Torborg, C. Samojłowicz, and K. Grela
4 Aqueous Media: Reactions of Carbonyl and Imino Groups
4.1 Reduction of Carbonyl and Imino Groups - X. Wu and J. Xiao
4.2 Alkylation, Allylation, and Benzylation of Carbonyl and Imino Groups - L. Zhao and C.-J. Li
4.3 Arylation, Vinylation, and Alkynylation of Carbonyl and Imino Groups - L. Zhao and C.-J. Li
4.4 Aldol Reaction - M. Woyciechowska, O. El-Sepelgy, and J. Mlynarski
4.5 Mannich Reaction and Baylis–Hillman Reaction - M. Benohoud and Y. Hayashi
5 Aqueous Media: Cyclization, Rearrangement, Substitution, Cross Coupling, Oxidation, and Other Reactions
5.1 Cycloaddition and Cyclization Reactions - G. Molteni
5.2 Pericyclic Rearrangements: Sigmatropic, Electrocyclic, and Ene Reactions - F. Fringuelli and O. Piermatti
5.3 Allylic and Aromatic Substitution Reactions - Y. Uozumi
5.4 Cross-Coupling and Heck Reactions - D. A. Alonso and C. Nájera
5.5 Ring Opening of Epoxides and Aziridines - C. Ogawa and S. Kobayashi
5.6 Asymmetric α-Functionalization of Carbonyl Compounds and - Alkylation of Enolates - S. Shirakawa and K. Maruoka
5.7 Oxidation of Alcohols, Allylic and Benzylic Oxidation, Oxidation of Sulfides - R. A. Sheldon
5.8 Free-Radical Reactions - H. Yorimitsu and K. Oshima
5.9 Polymerization - M. Ouchi and M. Sawamoto
6 Special Techniques with Water
6.1 Organic Synthesis “On Water” - A. Chanda and V. V. Fokin
6.2 Sub- and Supercritical Water - A. Kruse and E. Dinjus
6.3 β-Cyclodextrin Chemistry in Water - F. Hapiot and E. Monflier
7 Industrial Application
7.1 Hydroformylation - E. Wiebus, K. Schmid, and B. Cornils
7.2 Industrial Applications Other than Hydroformylation - Y. Mori and S. Kobayashi
8 Perspective: The New World of Organic Chemistry Using Water as Solvent - S. Kobayashi