Issue 2, 2001

Scope and limitations of the [1,2]-alkylsulfanyl (SMe, SEt and SCH2Ph) and sulfanyl (SH) migration in the stereospecific synthesis of substituted tetrahydrofurans

Abstract

Acid catalysed rearrangement of a series of 4-RS-1,3-diols (R = Me, Et, Bn and H) with toluene-p-sulfonic acid in dichloromethane gives stereospecifically substituted tetrahydrofurans via a [1,2]-SR shift in near quantitative yield. We comment on the structural variation of the migrating (RS) substituent and that of the migration origin and terminus on the outcome of the title reaction. We also report on the surprising similarity between an alkylsulfanyl (RS) and sulfanyl (SH) migrating group.

Supplementary files

Article information

Article type
Paper
Submitted
08 Sep 2000
Accepted
10 Nov 2000
First published
18 Dec 2000

J. Chem. Soc., Perkin Trans. 1, 2001, 138-143

Scope and limitations of the [1,2]-alkylsulfanyl (SMe, SEt and SCH2Ph) and sulfanyl (SH) migration in the stereospecific synthesis of substituted tetrahydrofurans

J. Eames, N. Kuhnert and S. Warren, J. Chem. Soc., Perkin Trans. 1, 2001, 138 DOI: 10.1039/B007284M

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