Alkynyliodonium salts in organic synthesis. Preparation of 2-substituted-3-p-toluenesulfonyldihydrofurans from 1-hydroxybut-3-ynyliodonium ethers via a formal stevens shift of a carbon group

Ken S. Feldman, Michelle Laci Wrobleski

Research output: Contribution to journalArticle

21 Scopus citations

Abstract

(equation presented) p-Toluenesulfinate addition to 1-hydroxybut-3-ynyliodonium ethers triggers a sequence of reactions which ultimately delivers 2-substituted-3-p-toluenesulfonyldihydrofuran products along with 3-p-toluenesulfonyldihydrofuran as a major byproduct. A putative 1,2-alkyl shift within an unsaturated oxonium ylide (Stevens rearrangement) accounts for the oxygen-to-carbon transfer of the alkyl group.

Original languageEnglish (US)
Pages (from-to)2603-2605
Number of pages3
JournalOrganic Letters
Volume2
Issue number17
StatePublished - Aug 24 2000

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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