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  • Title: Generation and cyclization of unsaturated carbamoyl radicals derived from S-4-pentynyl carbamothioates under tin-free conditions.
    Author: Benati L, Bencivenni G, Leardini R, Minozzi M, Nanni D, Scialpi R, Spagnolo P, Zanardi G.
    Journal: J Org Chem; 2006 Apr 14; 71(8):3192-7. PubMed ID: 16599618.
    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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