Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 8, Pages 2610-2618Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo100181h
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Funding
- Natural Sciences and Engineering Council of Canada
- Merck-Frosst Canada
- Universite de Sherbrooke
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We report a novel ring contraction allowing the direct conversion of N-chlorolactams to their corresponding ring-contraction N-heterocycles upon photolysis. Results show that the rearrangement occurs with a variety of N-chlorolactams and that the greater the substitution at the migrating carbon, the greater the yield of product. Importantly, stereochemistry at the migrating carbon is conserved in the product. Rearranged products were isolated as their methyl carbamates in yields varying from 17% to 58%, with the major side product being the recyclable parent lactam.
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