Regioselective Photochemical Rearrangement of N??Mesyloxylactams

S Pichette, S Aubert??Nicol, J Lessard…

Index: Pichette, Simon; Aubert-Nicol, Samuel; Lessard, Jean; Spino, Claude European Journal of Organic Chemistry, 2012 , # 7 p. 1328 - 1335

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Citation Number: 8

Abstract

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.