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Regioselective Photochemical Rearrangement of N ‐Mesyloxylactams
Author(s) -
Pichette Simon,
AubertNicol Samuel,
Lessard Jean,
Spino Claude
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101222
Subject(s) - chemistry , regioselectivity , ring strain , oxygen atom , ring (chemistry) , photochemistry , stereochemistry , oxygen , cope rearrangement , organic chemistry , catalysis , molecule
Abstract 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.