R. Bossio et al., STUDIES ON ISOCYANIDES AND RELATED-COMPOUNDS - AN UNUSUAL SYNTHESIS OF FUNCTIONALIZED SUCCINIMIDES, Synthesis, (12), 1997, pp. 1389-1390
The treatment of acetyl-N-(4-nitrophenyl)amino]-4-phenylbut-3-enoic ac
id N-cyclohexylamide (6a) with KOH does not afford the expected beta-l
actam la but the succinimide 7a, probably through a ring enlargement o
f compound Ia itself. A hypothesis on the reaction mechanism, which is
corroborated by experimental results, is formulated.