On the anomalous behaviour of certain 1-(4-methoxyphenyl)azetidin-2-ones towards cerium(IV) ammonium nitrate (CAN). Structure-reactivity studies

Article abstract of DOI:10.1016/0040-4020(95)01036-X

On treatment with CAN, acetylthiazolidinylazetidin-2-one 12 undergoes ring transformation to afford compound 22, similarly to azetidin-2-ones 2a and 2b studied earlier (all with like configurations at C-4 and C-2'). In contrast, acetylthiazolidinylazetidin-2-one 11 is N-demethoxy-phenylated under the same conditions, similarly to azetidin-2-ones 1a and 1b studied earlier (all with unlike configurations at C-4 and C-2'). Both epimers, with like as well as unlike configurations at C-4 and C-2'. of acetyloxazolidinyl derivative 7 are N-demethoxyphenylated by CAN. These observations support the mechanism, suggested earlier for the CAN induced novel ring transformation reaction.