摘要:
The reaction of 4-[((p-nitrobenzoyl)oxy)methyl]-3-cephem derivative 4 with bromine in methanol afforded a mixture of the 3-bromo-4-methoxy adducts 5 and 6 and of the unexpected 4-spiro orthoesters 7 and 8. The structure and configuration of 7 and 8 were demonstrated through the determination of the solid-state structure of 7 and by H-1 and C-13 NMR studies and chemical transformations. The mechanism and the stereochemical outcome of the reaction are discussed.