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Synthesis 2012; 44(17): 2723-2734
DOI: 10.1055/s-0032-1316746
DOI: 10.1055/s-0032-1316746
paper
S-Allyl Thiocarbamates from Allylic Alcohols by in situ [3,3]-Sigmatropic Rearrangement of a Thiocarbonyldiimidazole Adduct
Further Information
Publication History
Received: 18 April 2012
Accepted after revision: 22 June 2012
Publication Date:
30 July 2012 (online)
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.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
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