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Issue 10, 2018
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Thermal conversion of primary alcohols to disulfides via xanthate intermediates: an extension to the Chugaev elimination

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Abstract

Primary alcohols are converted into dialkyl disulfides via heating in situ generated O-alkyl S-difluoro(ethoxycarbonyl)methyl xanthates from ethyl bromodifluoroacetate and potassium xanthates, prepared from primary alcohols and carbon disulfide in the presence of KOH. The reaction mechanism is suggested as an alkyl C[1,3] shift followed by a radical mechanism. This extends to the Chugaev elimination which yields olefins. The current research provides easy access to dialkyl disulfides from commercially available primary alkanols.

Graphical abstract: Thermal conversion of primary alcohols to disulfides via xanthate intermediates: an extension to the Chugaev elimination

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Publication details

The article was received on 04 Jan 2018, accepted on 08 Feb 2018 and first published on 08 Feb 2018


Article type: Paper
DOI: 10.1039/C8OB00024G
Citation: Org. Biomol. Chem., 2018,16, 1659-1666
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    Thermal conversion of primary alcohols to disulfides via xanthate intermediates: an extension to the Chugaev elimination

    W. He, Y. Ding, J. Tu, C. Que, Z. Yang and J. Xu, Org. Biomol. Chem., 2018, 16, 1659
    DOI: 10.1039/C8OB00024G

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