A. Balsamo, M. Benvenuti, A. Lapucci
Mar 1, 1991
Citations
0
Influential Citations
3
Citations
Journal
Journal of Organic Chemistry
Abstract
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 1 H and 13 C NMR studies and chemical transformations. The mechanism and the stereochemical outcome of the reaction are discussed