Rearrangement of Allylic and Propargylic Alcohols Catalyzed by the Combined Use of tetrabutylammonium perrhenate (VII) and p-toluenesulfonic acid

Koichi Narasaka, Hiroyuki Kusama, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

67 Citations (Scopus)

Abstract

Allylic rearrangement and/or dehydration reaction of allylic alcohols proceeds smoothly by the use of catalytic amounts of tetrabutylammonium perrhenate and p-toluenesulfonic acid hydrate. Treatment of propargylic alcohols with the catalysts at room temperature affords the rearranged products, α,β-unsaturated carbonyl compounds, while, β,γ-unsaturated ketones are obtained as main products by the reaction in refluxing, 1,2-dichloroethane. The application of this catalytic system is also described for the preparation of some synthetic intermediates.

Original languageEnglish
Pages (from-to)2059-2068
Number of pages10
JournalTetrahedron
Volume48
Issue number11
DOIs
Publication statusPublished - 1992
Externally publishedYes

Keywords

  • allylic rearrangement
  • dehydration
  • p-toluenesulfonic acid
  • propargylic rearrangement
  • tetrabutylammonium perrhenate

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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