Vinyl Cations - 1st Edition - ISBN: 9780126637809, 9780323147088

Vinyl Cations

1st Edition

Editors: Peter Stang
eBook ISBN: 9780323147088
Imprint: Academic Press
Published Date: 1st January 1979
Page Count: 528
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Description

Vinyl Cations provides a comprehensive and detailed treatment of the reactive intermediate in which the electron-deficient carbon is an integral part of a ? unsaturation.

This book emphasizes that the reaction through vinyl cations is a viable pathway among the multitude of mechanistic routes for vinylic substitution. The aryl, ethynyl, and allenyl cations from the viewpoint of direct solvolytic generation from appropriate allenyl precursors are briefly discussed.

Other topics include the preparative aspects of electrophilic additions to alkynes, participation of allenyl bonds in solvolyses, and vinyl cations generated through diazonium ions. The nature of the cationic intermediates, migrations across the double bond, thiirenium ions, and species related to vinyl cations are likewise elaborated.

This publication is beneficial to chemists and researchers concerned with vinyl cations.

Table of Contents


Preface

Acknowledgment

1. Introduction and Historical Background

Text

References

2. Thermodynamics and Theoretical Calculations

I. Thermodynamic Considerations

II. Theoretical Calculations

References

3. Electrophilic Additions to Alkynes and Participation of the Triple Bond in Solvolysis

I. Mechanisms of Electrophilic Additions to Alkynes

II. Preparative Aspects of Electrophilic Additions to Alkynes

III. Triple-Bond Participation in Solvolysis

References

4. Electrophilic Additions to Allenes and Participation of the Allenyl Bond in Solvolysis

I. Additions to Allenes

II. Participation of Allenyl Bonds in Solvolyses

References

5. Bond Heterolysis

I. General Considerations

II. Vinyl Cations Generated Via Diazonium Ions

III. Direct Solvolytic Generation

IV. Stabilized Vinyl Cations

V. Alkylvinyl Substrates

References

6. Arylvinyl Cations Via Solvolysis

I. Introduction

II. Competing Substitution and Elimination Routes

III. Structural and Medium Effects on the Solvolysis

IV. Stereochemistry of Vinylic Solvolysis and the Structure of α-Arylvinyl Cations

V. Nature of the Cationic Intermediates

VI. β-Aryl Rearrangement in Triarylvinyl Systems

VII. Nonsolvolytic Methods for Generating α-Arylvinyl Cations from Vinylic Precursors

References

7. Rearrangement of Vinyl Cations

I. General Considerations

II. Migrations to the Double Bond

III. Migrations Across the Double Bond

References

8. Spectroscopic Evidence for Vinyl Cations

I. Alkynyl Cations

II. Vinyl Cations

III. Thiirenium Ions

References

9. Miscellaneous and Conclusions

I. Synthetic Uses of Vinyl Cations

II. Metal-Stabilized Vinyl Cations

III. Species Related to Vinyl Cations

IV. Conclusions and Prognosis

References

Subject Index

Details

No. of pages:
528
Language:
English
Copyright:
© Academic Press 1979
Published:
Imprint:
Academic Press
eBook ISBN:
9780323147088

About the Editor

Peter Stang