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 Citations (Scopus)

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

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Synthetic Chemistry Techniques
Ethers
Byproducts
ethers
Carbon
Salts
actuators
Oxygen
salts
preparation
carbon
shift
oxygen
synthesis
products
hydronium ion

All Science Journal Classification (ASJC) codes

  • Molecular Medicine

Cite this

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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.",
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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. / Feldman, Ken S.; Wrobleski, Michelle Laci.

In: Organic Letters, Vol. 2, No. 17, 24.08.2000, p. 2603-2605.

Research output: Contribution to journalArticle

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