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.
Generation and Cyclization of Unsaturated Carbamoyl Radicals Derived from S-4-Pentynyl Carbamothioates under Tin-Free Conditions / M. L. Benati; G. Bencivenni; R. Leardini; M. Minozzi; D. Nanni; R. Scialpi; P. Spagnolo; G. Zanardi. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 71:(2006), pp. 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.
