A practical synthesis of mixed allyl and allenesulfinates

Samuel Braverman; Tatiana Pechenick

doi:10.1055/s-2003-41038

A practical synthesis of mixed allyl and allenesulfinates

Samuel Braverman
, Tatiana Pechenick

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

A new, general, and efficient method for the preparation of mixed sulfoxylates (ROSOR′) by treatment of symmetrical dialkoxy disulfides (ROSSOR) with alcohols at room temperature has been found. Subsequent spontaneous [2,3]-sigmatropic rearrangements of mixed sulfoxylates such as alkyl allyl and alkyl propargyl sulfoxylates afford mixed alkyl allyl and alkyl allenesulfinates in good yield. The latter are not readily available by other routes.

Original language	English
Pages (from-to)	2079-2083
Number of pages	5
Journal	Synthesis
Issue number	13
DOIs	https://doi.org/10.1055/s-2003-41038
State	Published - 2003

Keywords

Alkenes
Alkynes
Dialkoxy disulfides
Sulfinates
[2,3]-sigmatropic rearrangements

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10.1055/s-2003-41038

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AB - A new, general, and efficient method for the preparation of mixed sulfoxylates (ROSOR′) by treatment of symmetrical dialkoxy disulfides (ROSSOR) with alcohols at room temperature has been found. Subsequent spontaneous [2,3]-sigmatropic rearrangements of mixed sulfoxylates such as alkyl allyl and alkyl propargyl sulfoxylates afford mixed alkyl allyl and alkyl allenesulfinates in good yield. The latter are not readily available by other routes.

KW - Alkenes

KW - Alkynes

KW - Dialkoxy disulfides

KW - Sulfinates

KW - [2,3]-sigmatropic rearrangements

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A practical synthesis of mixed allyl and allenesulfinates

Abstract

Keywords

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