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Issue 2, 2001
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Scope and limitations of the [1,2]-alkylsulfanyl (SMe, SEt and SCH2Ph) and sulfanyl (SH) migration in the stereospecific synthesis of substituted tetrahydrofurans<img border='0' src='http://www.rsc.org/images/entities/h2_char_200a.gif' alt=' '/>

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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.

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Publication details

The article was received on 08 Sep 2000, accepted on 10 Nov 2000 and first published on 18 Dec 2000


Article type: Paper
DOI: 10.1039/B007284M
Citation: J. Chem. Soc., Perkin Trans. 1, 2001, 138-143
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    Scope and limitations of the [1,2]-alkylsulfanyl (SMe, SEt and SCH2Ph) and sulfanyl (SH) migration in the stereospecific synthesis of substituted tetrahydrofurans<img border='0' src='http://www.rsc.org/images/entities/h2_char_200a.gif' alt=' '/>

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

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