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

Organic & Biomolecular Chemistry Pub Date: 2018-02-08 DOI: 10.1039/C8OB00024G

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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