Application of Copper(I)-Induced Thiophenoxide Removal to Ring Expansions or Chain Extensions of Aldehydes and Ketones. Detection, Isolation, and Independent Preparation of the α-Epoxy Thioether Intermediate

Theodore Cohen, David Kuhn, J R Falck

Research output: Contribution to journalArticle

79 Scopus citations

Abstract

Recent work from this laboratory1 has demonstrated that sulfur-stabilized carbonium ions can be readily generated in organic solvents under mild conditions by removal of a thiophenoxide ion from a thioacetal or thioketal using soluble cuprous trifluoromethanesulfonate (triflate).2 The procedure was applied to the syntheses of a variety of vinyl sulfides and of a furan. We now report applications which result in new synthetic procedures and which illustrate the high selectivity of the process.

Original languageEnglish (US)
Pages (from-to)4749-4751
Number of pages3
JournalJournal of the American Chemical Society
Volume97
Issue number16
DOIs
StatePublished - Aug 1 1975

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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