Pericyclic Reactions - 1st Edition - ISBN: 9780124705029, 9781483218656

Pericyclic Reactions

1st Edition

Organic Chemistry: A Series of Monographs, Vol. 35.2

Editors: Alan P. Marchand Roland E. Lehr
eBook ISBN: 9781483218656
Imprint: Academic Press
Published Date: 28th January 1976
Page Count: 342
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Pericyclic Reactions,Volume 35-II covers the theoretical approaches to pericyclic reactions and reviews of pericyclic reactions of reactive intermediates and of particular reaction types. The book discusses some of the experimental approaches used to establish the authenticity of an apparent pericyclic reaction; the transient and observable carbocation rearrangements; and orbital symmetry interactions which are “extra” stabilizing or destabilizing. The text then describes the pericyclic reactions of cumulenes; the cheletropic reactions; the applications of frontier molecular orbital theory to pericyclic reactions. A general theoretical model accommodating concerted reaction profiles for forbidden thermal reactions is also encompassed. Chemists and people involved in the study of pericyclic reactions will find the book invaluable.

Table of Contents


List of Contributors


Contents of Volume I

1 Carbocations

I. General Introduction

II. Electrocyclic Reactions

III. Cycloaddition and Cycloreversion Reactions

IV. Sigmatropic Reactions

V. Pericyclic, Longicyclic, and Laticyclic Stabilization


2 Pericyclic Reactions of Cumulenes

I. Introduction

II. Electronic Structure of Cumulenes

III. [2 + 2] Cycloadditions of Ketenes to Alkenes

IV. Ketene Dimerization

V. Ketene-Allene Cycloadditions

VI. [2 + 2] Cycloadditions of Allenes

VII. [2 + 2] Cycloadditions of Ketenimines

VIII. [2 + 2] Cycloadditions of Keteniminium Salts

IX. [2 + 4] Cycloadditions of Cumulenes

X. Cycloadditions of Vinylcumulenes


3 Cheletropic Reactions

I. Introduction

II. Sulfolene Reactions

III. Cheletropy in Other Systems

IV. Conclusion


4 Applications of Frontier Molecular Orbital Theory to Pericyclic Reactions

I. Introduction

II. The Development of the Frontier Molecular Orbital Method

III. The Frontier Orbital Approximation

IV. Practical Applications of Frontier Molecular Orbital Theory

V. Applications to Thermal Intermolecular Cycloadditions

VI. Applications to Thermal Intramolecular Reactions

VII. Photochemical Pericyclic Reactions

VIII. Conclusion


5 Thermally Forbidden Reactions

I. Introduction

II. Theory

III. Examples

IV. Conclusions


Author Index

Subject Index


No. of pages:
© Academic Press 1977
Academic Press
eBook ISBN:

About the Editor

Alan P. Marchand

Roland E. Lehr

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