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Start Over Descriptor "NITROGEN-HETEROCYCLES" Publisher elsevier b.v.
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2. Ring contraction of N-chlorolactams, a novel rearrangement

Author

Drouin, Alexandre and Lessard, Jean

Subjects
*CARBAMATES, *DICHLOROMETHANE, *CHLORIDES, *CHLORINE compounds
Abstract

Abstract: Upon photolysis in methylene chloride at −78°C, different N-chlorolactams underwent a novel ring contraction to the corresponding carbamoyl chlorides, which were converted to the methyl carbamates. The rearrangement is 100% stereoselective, occurring with retention of configuration at the migrating carbon center. The yields of isolated carbamates ranged from 40% to 57%, the other product being the parent lactam, 18% to 38%. [Copyright &y& Elsevier]

Published
2006
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