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Cation Radicals in the Synthesis and Reactions of Cyclobutanes

Cyclobutanes (2005)

  1. Nathan L. Bauld

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0327

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Bauld, N. L. 2009. Cation Radicals in the Synthesis and Reactions of Cyclobutanes. Patai's Chemistry of Functional Groups. .

Author Information

  1. The University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, TX, USA

Publication History

  1. Published Online: 15 DEC 2009

Abstract

  • 1
    Introduction
  • 2
    Historical
  • 3
    Energetic Considerations for Cation Radical/Neutral Cycloaddition Reactions
  • 4
    Novel Cation Radical Structures Encountered in Cation Radical/Neutral Cycloadditions
  • 5
    Mechanistic Considerations
  • 6
    Stereochemistry of Cation Radical Cyclobutanation
  • 7
    Other Early Cation Radical Cyclobutanation Precedents
  • 8
    Mechanistic Diversity
  • 9
    The Concerted (or Quasi-Concerted) Cycloaddition Mechanism
  • 10
    Mechanistic Considerations in Aminium Salt Initiated Cyclobutadimerizations
  • 11
    Cross Cyclobutanation
  • 12
    Cyclobutane Periselectivity in Cross Additions to Conjugated Dienes
  • 13
    The Competition between Cation Radical Cyclobutanation and Diels–Alder Cycloaddition
  • 14
    Steric Effects in Cation Radical Cyclobutanation
  • 15
    Diels–Alder Periselectivity in Reactions with Acyclic Dienes
  • 16
    Diels–Alder/Cyclobutanation Competition in Cation Radical Cycloadditions to Styrenes
  • 17
    Conformational Effects upon Periselectivity in Cation Radical/Neutral Cycloaddition Reactions
  • 18
    The Cation Radical Vinylcyclobutane (VCB) Rearrangement
  • 19
    Stereochemistry of the Cation Radical Vinylcyclobutane Rearrangement
  • 20
    The Cation Radical Arylcyclobutane Rearrangement
  • 21
    Intramolecular Cation Radical Cyclobutanation
  • 22
    Natural Product Synthesis via Cation Radical Cyclobutanation
  • 23
    Cation Radical Chain Cycloaddition Polymerization
  • 24
    Retrocyclobutanation
  • 25
    Cation Radical Cycloadditions Involving Alkynes
  • 26
    Cation Radical Chain Reactions of Alkene Cation Radicals with Dioxygen
  • 27
    Retroelectrocyclic Reactions of Cyclobutene Cation Radicals

Keywords:

  • cyclodimerization of N-vinylcarbazole and photosensitized electron transfer (PET);
  • hole transfer (HT) and electron transfer (ET);
  • cation radical/neutral cycloaddition reactions;
  • nonbonding 2p atomic orbital on carbon (NBAO);
  • cation radical cyclobutanation steric effects;
  • distonic cation radical in Ledwith mechanism;
  • cation radical cyclobutanation stereochemistry;
  • cross cyclobutanation