Trifuoroperacetic acid in consecutive Criegee rearrangement and carboxonium ions generation

Pavel A. Krasutsky, Igor V Kolomitsyn

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2 Scopus citations

Abstract

Recent achievements in the use of trifluoroperacetic acid (TFPAA) in consecutive Criegee rearrangement are covered in this review. Consecutive Criegee rearrangement promoted by TFPAA represents a new approach to this classic method in organic chemistry. The concept of selective double and triple O-insertion is described through the analysis of kinetic data, the overview of synthetic examples and studies of the reaction mechanisms. TFPAA in trifluoroacetic acid (TFAA) media is introduced as a specific reagent for consecutive Criegee rearrangement and for stable carboxonium ion generation. Heterolytic decarboxylation and bisperfluoroacyl peroxide synthesis are discussed as miscellaneous and useful reactions.

Original languageEnglish (US)
Pages (from-to)151-171
Number of pages21
JournalArkivoc
Volume2005
Issue number4
StatePublished - May 18 2005

Keywords

  • Baeyer-villiger reaction
  • Carboxonium ion
  • Criegee rearrangement
  • Decarboxylation
  • Oxygen insertion
  • Peroxide
  • Trifluoroperacetic acid

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