18. Rearrangements of Hydrazo, Azoxy and Azo Compounds

  1. Saul Patai Professor
  1. Robin A. Cox and
  2. Erwin Buncel

Published Online: 22 JUL 2004

DOI: 10.1002/0470023414.ch18

Hydrazo, Azo and Azoxy Groups, Volume 1 and Volume 2 (1975)

Hydrazo, Azo and Azoxy Groups, Volume 1 and Volume 2 (1975)

How to Cite

Cox, R. A. and Buncel, E. (1975) Rearrangements of Hydrazo, Azoxy and Azo Compounds, in Hydrazo, Azo and Azoxy Groups, Volume 1 and Volume 2 (1975) (ed S. Patai), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470023414.ch18

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. Department of Chemistry, Queen's University, Kingston, Ontario, Canada, K7L 3N6

Publication History

  1. Published Online: 22 JUL 2004
  2. Published Print: 1 JAN 1975

Book Series:

  1. PATAI'S Chemistry of Functional Groups

Book Series Editors:

  1. Saul Patai

Series Editor Information

  1. The Hebrew University, Jerusalem, Israel

ISBN Information

Print ISBN: 9780471669241

Online ISBN: 9780470023419

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Summary

This chapter contains sections titled:

  • General Introduction

  • Rearrangements of Hydrazo Compounds

    • The Benzidine Rearrangements

      • The Acid-catalysed Benzidine Rearrangement

        • Reaction Products

        • Kinetic and Other Mechanistic Studies

        • General vs. Specific Acid Catalysis

        • Reaction Intermediates

        • Requirements for an Acceptable Mechanism

        • Theories of Mechanism

        • The Polar-transition-state Theory

        • The Π-complex Theory

        • The Caged-radical Theory

        • Lukashevich's Theory

        • The C-protonated Intermediate Theory

      • The Thermal Benzidine Rearrangement

        • Products

        • Mechanism

      • The Photochemical Benzidine Rearrangement

      • Heterocyclic Hydrazo Compounds

    • Related Rearrangements

  • Rearrangements of Azoxy Compounds

    • The Wallach Rearrangement

      • Introduction

      • Reaction Products

      • Products in Acids Other Than Sulphuric

      • Isotopic Substitution Studies

        • Para-hydroxy Product

        • Ortho-hydroxy Product

        • Oxygen Migration in the Reactant

      • Reaction Intermediates

      • Kinetic Studies

      • Theories of Mechanism

        • The N,N-oxide Intermediate Mechanism

        • The Dicationic Intermediate Mechanism

        • The Quinonoid Intermediate Mechanism

      • Rearrangements Giving Ortho-hydroxy Products

    • Other Aromatic Azoxy Rearrangements

    • Aliphatic Azoxy Rearrangements

  • Rearrangements of Azo Compounds

    • Scope of Presentation

    • Azo–Hydrazone Tautomerism of Aromatic Azo Compounds

    • Tautomerism of Protonated Aromatic Azo Compounds

    • Tautomerism of Aliphatic Azo Compounds

    • Some Further Azo Rearrangements

  • Acknowledgments

  • References