Thermal Electrocyclic Reactions - 1st Edition - ISBN: 9780124762503, 9780323150453

Thermal Electrocyclic Reactions

1st Edition

Authors: Elliot Marvell
eBook ISBN: 9780323150453
Imprint: Academic Press
Published Date: 28th January 1980
Page Count: 434
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Description

Thermal Electrocyclic Reactions explores the applications of thermal electrocyclic reactions to stereospecific synthesis. This book is divided into nine chapters, and begins with a presentation of the theory of electrocylic reactions using orbital conversions through symmetry operations and correlation diagrams. Considerable chapters are devoted to various conjugate systems entering an electrocyclic process, including two-electron, four electron-three-, four-, and five-atom, and six electron-five-, and six-atom systems. The remaining chapters examine the electrocyclic reaction of longer systems, including eight or more π electrons, as well as conjugated systems with an odd number of electrons, which constitute a special case in the conservation of orbital symmetry. This book will be of great value to organic chemists and researchers.

Table of Contents


Preface

1 Introduction

Text

References

2 Theory

I. Origin of the Theory

II. Orbital Symmetry and Correlation Diagrams

III. The Frontier Orbital Approach

IV. Transition State Aromaticity—Hückel or Möbius

V. Alternative Theoretical Treatments

VI. Allowed, Forbidden, and Non-Concerted Routes

VII. Substituent Effects

VIII. Transition Metal Complexes

References

3 Two Electron Systems

I. Cyclopropyl-Allyl Cations

II. Cyclopropanone-Oxyallyl and Related Systems

References

4 Four Electron-Three Atom Systems

I. The Allene-Cyclopropyl Carbene Electrocyclization

II. The Aziridinyl Cation

III. The Cyclopropene-Vinylcarbene Reaction

IV. Azirine-Vinylnitrene-Iminocarbene Conversions

V. The Cyclopropyl Anion-Allyl Anion Process

VI. Heterocycles Isoelectronic with the Cyclopropyl Anion

References

5 Four Electron-Four and Five Atom Systems

I. Cyclobutene-Butadiene

II. Cyclobutenes Containing Heteroatoms

III. Four Electron-Five Atom Systems

References

6 Six Electron-Five Atom Systems

I. Pentadienylidenes

II. Butadienylnitrenes

III. Pentadienyl Anions

IV. Heteroatom Analogs of Pentadienyl Anions

V. Dipolar Systems

VI. Heteroatom Bearing Trienes

References

7 Six Electron-Six Atom Systems

I. cis-Hexatrienes-Cyclohexadienes

II. Heteroatomic Six Atom Systems

III. Uses in Synthesis

References

8 Conjugated Systems with Eight or More π Electrons

I. Eight Electron Systems

II. Ten Electron Systems

III. Long Conjugate Systems

References

9 Odd Electron Systems

I. Quantitative Calculations

II. Experimental Results

References

Index

Details

No. of pages:
434
Language:
English
Copyright:
© Academic Press 1980
Published:
Imprint:
Academic Press
eBook ISBN:
9780323150453

About the Author

Elliot Marvell