Jump to main content
Jump to site search

Issue 2, 2001
Previous Article Next Article

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

Author affiliations

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.

Back to tab navigation

Supplementary files

Article information


Submitted
08 Sep 2000
Accepted
10 Nov 2000
First published
18 Dec 2000

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

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

Search articles by author

Spotlight

Advertisements