Generation and Cyclization of Unsaturated Carbamoyl Radicals Derived from S-4-Pentynyl Carbamothioates under Tin-Free Conditions
The Journal of Organic Chemistry2006Vol. 71(8), pp. 3192–3197
Citations Over TimeTop 10% of 2006 papers
Luisa Benati, Giorgio Bencivenni, Rino Leardini, Matteo Minozzi, Daniele Nanni, Rosanna Scialpi, Piero Spagnolo, Giuseppe Zanardi
Abstract
The radical reaction of benzenethiol with S-4-pentynyl carbamothioates provides a valuable protocol for the tin-free generation of carbamoyl radicals, which arise from intramolecular substitution at sulfur by the initial sulfanylvinyl radicals. This procedure can be usefully employed to achieve N-benzylcarbamoyl radical 5-exo and 4-exo cyclizations leading, respectively, to pyrrolidinones and azetidinones, although, for the latter, it seems of lesser utility. Novel evidence is presented that N-tosyl-substituted carbamoyl radicals display a peculiar tendency to yield the corresponding isocyanate by beta-elimination of the tosyl radical.
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