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 language | English |
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Pages (from-to) | 2723-2734 |
Number of pages | 12 |
Journal | Synthesis (Germany) |
Volume | 44 |
Issue number | 17 |
DOIs | |
Publication status | Published - 2012 |
Keywords
- alcohols
- sigmatropic rearrangement
- stereospecificity
- sulfur
- thiocarbamates