Simple and condensed β-lactams. Part 27. Reaction of 1-(4-methoxyphenyl)-4-(tetrazol-5-yl)azetidin-2-one and 1-(4-methoxyphenyl)-5-(tetrazol-5-yl-methyl)pyrrolidin-2-one with Cerium(IV) ammonium nitrate (CAN)

Article abstract of DOI:10.1016/0040-4020(96)00539-X

Treatment of pyrrolidinone 3a with CAN under the usual conditions leads to formation of spiro compound 12, rather than to N-demethoxyphenylation. A study of the reactions of compound 12 with sodium chloride and sodium iodide furnished the proof for our assumption that the related non-isolable compounds 6 and 11 are the intermediates of the anomalous reactions of compounds 1a and 2a, respectively, with CAN.