Chapter 9. Rearrangements Involving Triple Bonded Groups

  1. Professor Saul Patai
  1. D. Whittaker

Published Online: 29 JUL 2004

DOI: 10.1002/0470024771.ch9

Triple Bonded Functional Groups (1994)

Triple Bonded Functional Groups (1994)

How to Cite

Whittaker, D. (1994) Rearrangements Involving Triple Bonded Groups, in Triple Bonded Functional Groups (1994) (ed S. Patai), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470024771.ch9

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. Department of Chemistry, University of Liverpool, L69 3BX, UK

Publication History

  1. Published Online: 29 JUL 2004
  2. Published Print: 31 OCT 1994

Book Series:

  1. PATAI'S Chemistry of Functional Groups

Book Series Editors:

  1. Professor Saul Patai and
  2. Professor Zvi Rappoport

Series Editor Information

  1. The Hebrew University, Jerusalem, Israel

ISBN Information

Print ISBN: 9780471935599

Online ISBN: 9780470024775

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Summary

This chapter contains sections titled:

  • Introduction

  • Rearrangements Involving Acetylenes

    • Alkyne–Allene Interconversions

      • Rearrangements of Hydrocarbons

      • Rearrangements of Lithium Alkynes

      • Rearrangements of Tin Alkynes

      • Rearrangements of Alkynyltrimethylsilanes

      • Rearrangements of Mercury Alkynes

      • Rearrangements of Alkynyl Selenoxides

      • Rearrangements of Alkynyl Phosphines

    • Alkyne Dimerizations

    • Acetylene–Vinylidene Interconversion

    • Rearrangement of Alkyne–Metal Complexes

      • Triple-bond Cleavage

      • Alkyne Metathesis

      • Insertion into Metal–Carbon Bonds

      • Polymerization of Alkynes

    • Rearrangements Involving Reactions of Alkynes with Electrophiles

    • Triple-bond Participation

      • Homopropargylic Rearrangements

      • Remote Triple-bond Participation

        • Interaction with Ketones

        • Interaction with Cations

        • Interaction with Radicals

        • Interaction with Organometallic Catalysts

    • Cycloaddition Reactions of Alkynes

    • Sigmatropic Rearrangements of Alkynes

    • Thermal and Photochemical Rearrangements of Alkynes

      • Concerted Rearrangements

      • Formation of Radical Cations

  • Rearrangements Involving Cyanides

    • Rearrangements to Isocyanides and Ketenimines

    • Rearrangements Involving Metal Complexes

    • Rearrangements Involving Cations

      • Effect of the Cyano Group on Neighbouring Carbocations

      • Through-space Interactions of Carbocations with Cyanides

    • Rearrangements Involving Carbenes and Nitrenes

    • Rearrangements Involving Radicals

    • Photochemical Rearrangements

    • Cycloaddition Reactions of Cyanides

    • Sigmatropic Rearrangements of Cyanides

  • Rearrangements Involving Isocyanides

    • Insertion Reactions of Isocyanides

    • Rearrangements Involving Carbocations

    • Reactions with Radicals

    • Rearrangements Involving Metal Complexes

    • Cycloaddition Reactions of Isocyanides

  • Rearrangements Involving Arynes

  • Rearrangements Involving Diazo and Diazonium Groups

    • Isomerization of Diazo Compounds

    • Rearrangements Involving Metal Complexes

    • Addition Reactions of Diazo Compounds

      • Nucleophilic Addition

      • Cycloaddition

    • Rearrangements Involving Diazonium Ions

      • Formation of Aliphatic Diazonium Ions

      • Reactions of Diazonium Ions

      • Rearrangement of Aliphatic Diazonium Ions

      • Formation of Carbocations from Aliphatic Diazonium Ions

      • Rearrangements During Amine Nitrosation

      • Aryldiazonium Ions

      • Addition Reactions of Aryldiazonium Ions

      • Substitution Reactions of Aryldiazonium Ions

    • Rearrangements Involving Carbenes and Carbenoids

      • Formation of Carbenes

      • Rearrangements of Carbenes

        • Insertion into a C[BOND]H Bond

        • Insertion into a C[BOND]C1 Bond

        • Alkene-forming Insertions

        • Ylide Formation

        • Insertion into OH Bonds

        • Insertion into BH Bonds

        • Cyclopropane Formation

        • Fragmentation Reactions

        • Carbene-to-carbene Rearrangements

      • Vinyl Carbenes

      • Alkynyl Carbenes

      • Phosphinocarbenes

      • Germylenes

      • Silylenes

      • Carbenoid Rearrangements

    • Rearrangements of Diazoketones

      • The Wolff Rearrangement

      • The Vinylogous Wolff Rearrangement

    • Rearrangements of Ketocarbenes

    • Acid-catalysed Rearrangements of α-diazoketones

    • Rearrangements of α-keto Carbenoids

      • Insertion into a C[BOND]H Bond

      • Insertion into an O[BOND]H Bond

      • Addition to Multiple Bonds

      • Formation of Ylides

      • Diazophosphonate Reactions

    • Addition Reactions of α-diazoketones

  • References