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Sulphones in Organic Synthesis - 1st Edition - ISBN: 9780080402840, 9781483292793

Sulphones in Organic Synthesis, Volume 10

1st Edition

Author: N S. Simpkins
Editor: Patrick Perlmutter
eBook ISBN: 9781483292793
Imprint: Pergamon
Published Date: 28th January 1993
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Table of Contents

Chapter and selected section headings: Introduction to Sulphone Chemistry. The Preparation of Sulphones. Simple Alkyl Aryl and Dialkyl Sulphones. Oxidation of sulphides. Vinyl Sulphones. Ionic and radical additions to alkenes, alkynes and allenes. Allylic, Allenic, Alkynyl and Aryl Sulphones. Palladium-catalysed synthesis of allylic sulphones. Functionalised Sulphones. Hydroxy and alkoxy sulphones. Sulphonyl Carbanions. Introduction to Sulphonyl Carbanions. The structure of sulphonyl carbanions. Reactions of Simple Sulphonyl Carbanions. Alkylations. Reaction with epoxides. Reactions of Additionally Stabilised Sulphonyl Carbanions. Ketosulphones and related systems. Sulphonyl Polyanions. Polyanions from simple sulphones. Additions to Unsaturated Sulphones. Heteroatom Nucleophiles. Nitrogen nucleophiles. Non-Stabilised Organometallics. Enolates, Related Anions and Miscellaneous Carbon Nucleophiles. Cyclopropanations. Radical Additions. Rearrangements of Sulphones. Ring Expansions and Fragmentations. Sulphinate to Sulphone Rearrangements. 1,3-Rearrangements of Allylic Sulphones. The Truce-Smiles Rearrangement. Miscellaneous Rearrangements. Cycloaddition Chemistry of Unsaturated Sulphones. [2+2] Cycloadditions. [3+2] Cycloadditions. [4+2] Cycloadditions. Carbon-Carbon Double-Bond Formation by Sulphone Elimination. The Julia Olefination Reaction. Alternative beta-Eliminations of Sulphones. The Ramberg-Bäcklund Reaction. Chemistry of Cyclic Sulphones. Three-Membered Ring Sulphones. Four-Membered Ring Sulphones. Five-Membered Ring Sulphones. Functionalised Normal-Sized Rings. Larger Ring Sulphones. Desulphonylation. Simple Alkyl Aryl and Dialkyl Sulphones. Allylic Sulphones. Vinyl Sulphones. Functionalised Sulphones. Sulphone Reduction. Index.


Over the last twenty years the use of sulphones in organic synthesis has increased dramatically, the synthetic repertoire of sulphones having been developed to such an extent as to rival the carbonyl functionality for versatility. Not only have sulphones been employed in a great many synthetic methodologies, enabling the preparation of a vast array of functionalised products, but the sulphone group has also proved to be of enormous value in many of the most demanding and sophisticated total syntheses carried out in recent years. This book describes in detail all of the important sulphone chemistry employed in organic synthesis, ranging from the well-established sulphone-mediated methods to less familiar sulphone reactions and very recent discoveries of synthetic potential.


For undergraduate and postgraduate courses in organic chemistry.


© Pergamon 1993
28th January 1993
eBook ISBN:


@qu:The presentation is lucid, full documentation is provided... The book will be valuable as a reference source. @source:Aslib Book Guide @from:Richard Taylor @qu:This is a readable, well illustrated and well designed book with extensive references up to 1991... I have aleady found this to be an invaluable research source book and it would also form an excellent course book for a series of postgraduate lectures... As with previous titles Sulphones in Organic Synthesis is a must for the library and highly recommended for personal purchase. @source:Chemistry and Industry @from:M. Wills @qu:Chapter three describes the reactions of sulphonyl carbanions, which represent the cornerstone of sulphone chemistry. It is in the introduction to this chapter that the author's obviously extensive knowledge of sulphone chemistry is most critical. In this section all of the relevant reported work is elegantly disseminated in a concise account which amounts to a riveting piece of scientific analysis... In summary this is an excellent book, very well researched and comprehensive in scope, yet concise and easy to read. It also provides a good source of examples of mechanistic problems for post-graduate students, especially in the chapter on rearrangements! @source:Chemistry in Britain

Ratings and Reviews

About the Author

N S. Simpkins

Affiliations and Expertise

Department of Chemistry, University of Nottingham, UK

About the Editor

Patrick Perlmutter

Patrick Perlmutter is Adjunct Professor of Chemistry at La Trobe University in Australia. He has been a university academic for 35 years with a highly active research group specialising in synthesis and new synthetic methods including conjugate additions, catalysis, total synthesis, medicinal chemistry and chemical biology. His research group has generated approximately 200 peer-reviewed publications in that time.

Affiliations and Expertise

Adjunct Professor of Chemistry La Trobe University, Australia