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

Gaëlle Mingat, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

5 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2723-2734
Number of pages12
JournalSynthesis (Germany)
Volume44
Issue number17
DOIs
Publication statusPublished - 2012

Keywords

  • alcohols
  • sigmatropic rearrangement
  • stereospecificity
  • sulfur
  • thiocarbamates

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