Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 7, Pages 1328-1335Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101222
Keywords
N-Mesyloxylactams; Rearrangement; Photochemistry; Ring contraction; Regiochemistry
Categories
Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Fonds quebecois de la recherche sur la nature et les technologies (FQRNT)
- Universite de Sherbrooke
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N-Mesyloxylactams can undergo ring contraction either by C-3 (usually observed) or C-5 migration. C-5 migration can occur when the C-3 migration product possesses ring strain, but it does not usually compete with C-3 migration. The greater preference for C-3 migration is due to the carbonyl oxygen atom, which greatly stabilizes the intermediate.
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