Cyclobutadiene and Related Compounds

Cyclobutadiene and Related Compounds

1st Edition - January 1, 1967

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  • Author: M.P. Cava
  • eBook ISBN: 9780323163125

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Cyclobutadiene and Related Compounds describes the four-membered carbocyclic compounds that have only trigonally hybridized carbon atoms in the ring. The book discusses the chemistry of cyclobutadiene and the substituted cyclobutadienes, including the preparation of cyclobutadiene-metal complexes that can be done in four ways. These are (1) by reaction of acetylenes with transition metal compounds, (2) from cyclobutenyl metal complexes, (3) by transformation of other cyclobutadiene-metal complexes, and (4) by trapping cyclobutadienes with transitional metal compounds. The text also describes cyclobutadiene dianion, the chemistry of the cyclobutadienequinones, the condensed methylenecyclobutene aromatic systems, and the higher aromatic analogs of benzocyclobutadiene. The book cites proofs of the structure of biphenylene using chemical and physical methods. The text also presents theoretical aspects of the cyclobutadiene problem including studies regarding the ?-electronic state of cyclobutadiene; the comparisons of some of these studies; the framework energies and Janh-Teller considerations; and the substituted cyclobutadienes, cyclobutadiene divalent ions, and metal complexes. This book is suitable for scientists and researchers working in the field of organic chemistry, analytical chemistry, and molecular physics.

Table of Contents

  • Preface

    Chapter 1. Cyclobutadiene

    A. History

    B. Generation of Cyclobutadiene and Substituted Cyclobutadienes

    C. Unsuccessful Approaches to the Cyclobutadienes

    D. Evidence of the Triplet Diradical Character of the Cyclobutadienes

    E. Chemistry of Cyclobutadiene and the Substituted Cyclobutadienes


    Chapter 2. The Cyclobutadiene—Metal Complexes

    A. History

    B. Preparation of Cyclobutadiene—Metal Complexes

    C. Cyclobutadiene—Metal Complexes as Transient Intermediates

    D. Unsuccessful Approaches to the Cyclobutadiene—Metal Complexes

    E. Chemistry of the Cyclobutadiene—Metal Complexes

    F. Physical Properties of the Cyclobutadiene—Metal Complexes


    Chapter 3. Cyclobutadiene Divalent Ions

    A. History

    B. Cyclobutadiene Dication

    C. Cyclobutadiene Dianion


    Chapter 4. Cyclobutadienequinone

    A. History

    B. Synthesis of Cyclobutadienequinones

    C. Unsuccessful Attempts to Prepare Cyclobutadienequinones

    D. Chemistry of the Cyclobutadienequinones

    E. Physical Properties of the Cyclobutadienequinones


    Chapter 5. Methylene Analogs of Cyclobutadienequinone

    A. History

    B. Dimethylenecyclobutenes

    C. Tetramethylenecyclobutanes

    D. Trimethylenecyclobutanone and the Dimethylenecyclobutanediones

    E. Condensed Methylenecyclobutene Aromatic Systems


    Chapter 6. Benzocyclobutadiene

    A. History

    B. Generation of Benzocyclobutadiene and Substituted Benzocyclobutadienes

    C. Unsuccessful Approaches to the Benzocyclobutadienes

    D. Chemistry of Benzocyclobutadiene


    Chapter 7. Benzocyclobutadienequinone

    A. History

    B. Synthesis of Benzocyclobutadienequinone

    C. Unsuccessful Attempts to Prepare Benzocyclobutadienequinone

    D. Physical Properties of Benzocyclobutadienequinone

    E. Chemistry of Benzocyclobutadienequinone


    Chapter 8. Methylene Analogs of 1,2-Benzocyclobutadienequinone

    A. History

    B. 2-Methylenebenzocyclobutenones

    C. 1, 2-Dimethylenebenzocyclobutenes


    Chapter 9. Higher Aromatic Analogs of Benzocyclobutadiene

    A. History

    B. Naphtho[b]cyclobutadiene

    C. Phenanthro[l]cyclobutadiene


    Chapter 10. Biphenylene

    A. History

    B. Synthesis of Biphenylenes

    C. Unsuccessful Approaches to the Biphenylenes

    D. Proof of Structure of Biphenylene

    E. Chemistry of Biphenylene

    F. Physical Properties of Biphenylene

    G. Chemical and Physical Properties of Substituted Biphenylenes


    Chapter 11. The Benzobiphenylenes

    A. History

    B. Synthesis of Benzo- and Dibenzobiphenylenes

    C. Unsuccessful Approaches to the Benzobiphenylenes

    D. Chemical and Physical Properties of the Benzo- and Dibenzobiphenylenes

    E. Higher Aromatic Analogs of the Benzobiphenylenes

    F. Heterocyclic Benzobiphenylenes


    Chapter 12. Theoretical Aspects of the Cyclobutadiene Problem

    A. The π-Electronic States of Cyclobutadiene

    B. Some Conclusions and Comparisons

    C. Jahn-Teller Considerations

    D. Substituted Cyclobutadienes, Condensed Aromatic Cyclobutadienes, and Cyclobutadiene—Metal Complexes



    Appendix. Abstracts of Papers Appearing in the Literature in 1964—1965

    Author Index

    Subject Index

Product details

  • No. of pages: 518
  • Language: English
  • Copyright: © Academic Press 1967
  • Published: January 1, 1967
  • Imprint: Academic Press
  • eBook ISBN: 9780323163125

About the Author

M.P. Cava

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