S-allyl thiocarbamates from allylic alcohols by in situ [3,3]-sigmatropic rearrangement of a thiocarbonyldiimidazole adduct

Gaëlle Mingat, Jonathan Clayden

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Treatment of allylic alcohols with thiocarbonyldiimidazole generates an unstable O-allyl imidazolyl thione ester, which rearranges spontaneously and in high yield to the corresponding S-allyl imidazolyl thiol ester. Displacement of the imidazole by N-alkylanilines in the presence of a nucleophilic catalyst (HOBt or ECHIA) gives S-allyl N-aryl thiocarbamates in excellent yields (up to 97%) over two steps. © Georg Thieme Verlag Stuttgart New York.
    Original languageEnglish
    Pages (from-to)2723-2734
    Number of pages11
    JournalSynthesis: journal of synthetic organic chemistry
    Volume44
    Issue number17
    DOIs
    Publication statusPublished - 2012

    Keywords

    • alcohols
    • sigmatropic rearrangement
    • stereospecificity
    • sulfur
    • thiocarbamates

    Fingerprint

    Dive into the research topics of 'S-allyl thiocarbamates from allylic alcohols by in situ [3,3]-sigmatropic rearrangement of a thiocarbonyldiimidazole adduct'. Together they form a unique fingerprint.

    Cite this