Ylid Chemistry - 1st Edition - ISBN: 9780123957788, 9780323162791

Ylid Chemistry

1st Edition

Authors: A.W. Johnson
eBook ISBN: 9780323162791
Imprint: Academic Press
Published Date: 1st January 1966
Page Count: 398
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Organic Chemistry, Volume 7: Ylid Chemistry focuses on the physical and chemical properties of ylids. This book discusses the Wittig synthesis of olefins, which involves the reaction between carbonyl compounds and phosphonium ylids. Organized into two parts encompassing nine chapters, this book starts with an overview of the definition of ylids as a substance in which a carbanion is attached directly to a heteroatom transporting a high degree of positive charge. This text then examines the unique stabilization that afforded the carbanions by the presence of the adjacent 'onium atom group, which is the special characteristic of ylids. Other chapters consider the general structure of phosphonium ylids, which virtually has no limitation on the nature of the X groups on phosphorus. This book discusses as well the Wittig reaction involving a condensation-elimination between a phosphonium ylid and ketone. The final chapter deals with the various aspects of the chemistry of sulfur ylids. This book is a valuable resource for chemists.

Table of Contents


1. Introduction References

Part 1 Ylids of Phosphorus

2. Introduction to Phosphorus Ylids References 3. Phosphonium Ylids I. Preparation of Phosphonium Ylids II. Structure and Physical Properties of Phosphonium Ylids III. Reactions of Phosphonium Ylids Appendix References 4. The Wittig Reaction I. Experimental Conditions of the Wittig Reaction II. Scope and Limitations of the Wittig Reaction III. Applications of the Wittig Reaction IV. Mechanism of the Wittig Reaction V. Stereochemistry of the Wittig Reaction Appendix References 5. Other Phosphorus Ylids I. Phosphinoxy Carbanions II. Phosphonate Carbanions III. Miscellaneous Phosphorus Carbanions References 6. Iminophosphoranes I. Preparation of Iminophosphoranes II. Reactions of Iminophosphoranes III. Iminotrihalophosphoranes IV. Oxygenated Iminophosphoranes V. The Structure of Iminophosphoranes VI. Phosphinazines References

Part 2 Ylids of other Heteroatoms

7. Nitrogen Ylids I. Ammonium Ylids II. Pyridinium Ylids III. Nitrogen Imines IV. Diazo Compounds V. Rearrangements via Nitrogen Ylids VI. The Role of Nitrogen Ylids in the Hofmann Degradation References 8. Arsenic and Antimony Ylids I. Introduction II. Arsonium Ylids III. Iminoarsenanes IV. Stibonium Ylids and Imines References 9. Sulfur Ylids I. Introduction II. Sulfonium Ylid III. Other Sulfur Ylids IV. Iminosulfuranes Appendix References

Author Index Subject Index


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© Academic Press 1966
Academic Press
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About the Author

A.W. Johnson

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