학술논문
Generation and Cyclization of Unsaturated Carbamoyl Radicals Derived from S-4-Pentynyl Carbamothioates under Tin-Free Conditions.
Document Type
Article
Author
Source
Subject
*RADICALS (Chemistry)
*RING formation (Chemistry)
*CHEMICAL reactions
*PYRROLIDINE
*LACTAMS
*CHEMISTRY
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Language
ISSN
0022-3263
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 β-elimination of the tosyl radical. [ABSTRACT FROM AUTHOR]