1259430-50-6Relevant articles and documents
Regioselective photochemical rearrangement of N-mesyloxylactams
Pichette, Simon,Aubert-Nicol, Samuel,Lessard, Jean,Spino, Claude
, p. 1328 - 1335 (2012/04/05)
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. Studies of the photochemical rearrangement of N-mesyloxylactams showed that the lone pair of the carbonyl oxygen atom, and not the degree of the substitution atthe migrating carbon atoms, is the governing factor in the regioselectivity of the reaction. Copyright