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  • Title: Thermal conversion of primary alcohols to disulfides via xanthate intermediates: an extension to the Chugaev elimination.
    Author: He W, Ding Y, Tu J, Que C, Yang Z, Xu J.
    Journal: Org Biomol Chem; 2018 Mar 07; 16(10):1659-1666. PubMed ID: 29446434.
    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.
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