21. Cyclopropenes

  1. Zvi Rappoport
  1. Brian Halton1 and
  2. Martin G. Banwell2,†

Published Online: 28 JAN 2005

DOI: 10.1002/0470023449.ch21

Cyclopropyl Group: Volume 1 and Volume 2 (1987)

Cyclopropyl Group: Volume 1 and Volume 2 (1987)

How to Cite

Halton, B. and Banwell, M. G. (1987) Cyclopropenes, in Cyclopropyl Group: Volume 1 and Volume 2 (1987) (ed Z. Rappoport), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470023449.ch21

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. 1

    Department of Chemistry, Victoria University of Wellington, New Zealand

  2. 2

    Department of Chemistry, University of Auckland, New Zealand

  1. Department of Organic Chemistry, University of Melbourne, Parkville, Victoria 3052, Australia

Publication History

  1. Published Online: 28 JAN 2005
  2. Published Print: 28 OCT 1987

Book Series:

  1. PATAI'S Chemistry of Functional Groups

Book Series Editors:

  1. Saul Patai

ISBN Information

Print ISBN: 9780471917380

Online ISBN: 9780470023440

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Summary

This chapter contains sections titled:

  • Introduction

  • Synthesis of Cyclopropenes

    • Addition of Carbenes and Carbenoids to Alkynes

    • The Cyclization of α,β-unsaturated (Vinyl) Carbenes

    • 1,2-elimination Reactions

    • Alder–Rickert (Retrodiene) Cleavage

    • Miscellaneous Cyclopropene Syntheses

    • Synthesis of Cyclopropenones and Derivatives

    • Synthesis of Methylenecyclopropenes (Triafulvenes)

  • Physical and Theoretical Aspects of Cyclopropenes

  • Reactions of Cyclopropenes

    • Reactions Proceeding with Ring Retention

      • Substitution at C(1)/C(2)

      • Substitution at C(3)

      • Functionalization Remote from the Ring

      • Cyclopropene-methylenecyclopropane Rearrangements

      • Simple Additions to the Double Bond

      • Cycloaddition Reactions

        • [2+1] Cycloadditions

        • [2+2] Cycloadditions

        • [2+4] Cycloadditions

        • Dipolar [2+3] Cycloadditions

    • Reactions Proceeding with Ring Cleavage

      • Thermal Reactions

      • Photochemical Reactions

      • Reactions with Electrophiles

      • Reactions with Nucleophiles

      • By Metal Catalysis

      • By Oxidation

      • Cyclopropenylcarbinyl Cation Intervention

  • Organometallic Derivatives

    • Complexation with Ring Retention

    • Complexation with Ring Cleavage

    • Theoretical Aspects

  • Aspects of Cyclopropenone Chemistry

    • Physical and Theoretical Aspects of Cyclopropenones

    • Reactions of Cyclopropenones

      • Decarbonylation

      • Reduction

      • Oxidation

      • Reaction with Electrophiles

      • Reaction with Nucleophiles

      • Cycloaddition Reactions of Cyclopropenones

      • Organometallic Derivatives of Cyclopropenones

    • Hydroxycyclopropenones

    • Heteroatom Derivatives of Cyclopropenones

      • Cyclopropenethiones

      • Cyclopropenimines

  • Methylenecyclopropenes

    • Physical and Theoretical Aspects

    • Chemical Reactivity 1314

      • Oxidation and Reduction Processes

      • Reactions with Electrophiles and Nucleophiles

      • Cycloaddition Reactions

        • [2+2] Cycloadditions

        • [2+4] Cycloadditions

        • Dipolar [2+3] Cycloadditions

      • Organometallic Derivatives

  • The Cyclopropenyl Cation, Anion, Radical and Carbene

    • The Cyclopropenyl Cation

    • The Cyclopropenyl Radical

    • The Cyclopropenyl Anion

    • Cyclopropenylidene

  • References