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 reaction at sulfur by the initial sulfanylvinyl radicals. The procedure can be usefully employed to achieve N-benzylcarbamoyl radical 5-exo and 4-exo cyclizations leading, respectively, to pyrrolidinones and azetidinones.
M. L. Benati, G. Bencivenni, R. Leardini, M. Minozzi, D. Nanni, R. Scialpi, et al. (2006). Generation and Cyclization of Unsaturated Carbamoyl Radicals Derived from S-4-Pentynyl Carbamothioates under Tin-Free Conditions. JOURNAL OF ORGANIC CHEMISTRY, 71, 3192-3197 [10.1021/jo0602064].
Generation and Cyclization of Unsaturated Carbamoyl Radicals Derived from S-4-Pentynyl Carbamothioates under Tin-Free Conditions
BENATI, MARIA LUISA;BENCIVENNI, GIORGIO;LEARDINI, RINO;MINOZZI, MATTEO;NANNI, DANIELE;SCIALPI, ROSANNA;SPAGNOLO, PIERO;ZANARDI, GIUSEPPE
2006
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 reaction at sulfur by the initial sulfanylvinyl radicals. The procedure can be usefully employed to achieve N-benzylcarbamoyl radical 5-exo and 4-exo cyclizations leading, respectively, to pyrrolidinones and azetidinones.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
