Thermal Electrocyclic Reactions

Thermal Electrocyclic Reactions

1st Edition - January 28, 1980

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  • Author: Elliot Marvell
  • eBook ISBN: 9780323150453

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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



    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


    3 Two Electron Systems

    I. Cyclopropyl-Allyl Cations

    II. Cyclopropanone-Oxyallyl and Related Systems


    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


    5 Four Electron-Four and Five Atom Systems

    I. Cyclobutene-Butadiene

    II. Cyclobutenes Containing Heteroatoms

    III. Four Electron-Five Atom Systems


    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


    7 Six Electron-Six Atom Systems

    I. cis-Hexatrienes-Cyclohexadienes

    II. Heteroatomic Six Atom Systems

    III. Uses in Synthesis


    8 Conjugated Systems with Eight or More π Electrons

    I. Eight Electron Systems

    II. Ten Electron Systems

    III. Long Conjugate Systems


    9 Odd Electron Systems

    I. Quantitative Calculations

    II. Experimental Results



Product details

  • No. of pages: 434
  • Language: English
  • Copyright: © Academic Press 1980
  • Published: January 28, 1980
  • Imprint: Academic Press
  • eBook ISBN: 9780323150453

About the Author

Elliot Marvell

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