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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Description

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


Preface

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

Details

No. of pages:
398
Language:
English
Copyright:
© Academic Press 1966
Published:
Imprint:
Academic Press
eBook ISBN:
9780323162791

About the Author

A.W. Johnson