Facile preparation and rearrangement of allylic dialkoxy disulfides

Samuel Braverman; Tatiana Pechenick

doi:10.1016/s0040-4039(01)02174-8

Facile preparation and rearrangement of allylic dialkoxy disulfides

Samuel Braverman, Tatiana Pechenick

Department of Chemistry

Bar-Ilan University

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

22 Scopus citations

Abstract

Allylic dialkoxy disulfides were obtained in good yields and their reactivity has been investigated. Similarly to allylic sulfoxylates, these esters undergo double [2,3]-sigmatropic rearrangement to the appropriate vic-disulfoxides. The latter, being unstable, undergoes spontaneous rearrangement to the corresponding thiosulfonates.

Original language	English
Pages (from-to)	499-502
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	3
DOIs	https://doi.org/10.1016/s0040-4039(01)02174-8
State	Published - 14 Jan 2002

Keywords

Allylic dialkoxy disulfides
Sigmatropic rearrangement
Thiosulfonates
Vic-disulfoxides

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10.1016/s0040-4039(01)02174-8

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abstract = "Allylic dialkoxy disulfides were obtained in good yields and their reactivity has been investigated. Similarly to allylic sulfoxylates, these esters undergo double [2,3]-sigmatropic rearrangement to the appropriate vic-disulfoxides. The latter, being unstable, undergoes spontaneous rearrangement to the corresponding thiosulfonates.",

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AB - Allylic dialkoxy disulfides were obtained in good yields and their reactivity has been investigated. Similarly to allylic sulfoxylates, these esters undergo double [2,3]-sigmatropic rearrangement to the appropriate vic-disulfoxides. The latter, being unstable, undergoes spontaneous rearrangement to the corresponding thiosulfonates.

KW - Allylic dialkoxy disulfides

KW - Sigmatropic rearrangement

KW - Thiosulfonates

KW - Vic-disulfoxides

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Facile preparation and rearrangement of allylic dialkoxy disulfides

Abstract

Keywords

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