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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.
1. Introduction and Historical Background
2. Thermodynamics and Theoretical Calculations
I. Thermodynamic Considerations
II. Theoretical Calculations
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
4. Electrophilic Additions to Allenes and Participation of the Allenyl Bond in Solvolysis
I. Additions to Allenes
II. Participation of Allenyl Bonds in Solvolyses
5. Bond Heterolysis
I. General Considerations
II. Vinyl Cations Generated Via Diazonium Ions
III. Direct Solvolytic Generation
IV. Stabilized Vinyl Cations
V. Alkylvinyl Substrates
6. Arylvinyl Cations Via Solvolysis
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
7. Rearrangement of Vinyl Cations
I. General Considerations
II. Migrations to the Double Bond
III. Migrations Across the Double Bond
8. Spectroscopic Evidence for Vinyl Cations
I. Alkynyl Cations
II. Vinyl Cations
III. Thiirenium Ions
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
- No. of pages:
- © Academic Press 1979
- 1st January 1979
- Academic Press
- eBook ISBN:
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