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 1H and 13C NMR studies and chemical transformations. The mechanism and the stereochemical outcome of the reaction are discussed.

Uncommon formation of spiro orthoesters in the bromomethoxylation reaction of a 4-[(aroyloxy)methyl]-3-cephem derivative

LAPUCCI, ANNALINA;NENCETTI, SUSANNA;ROSSELLO, ARMANDO;
1991-01-01

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 1H and 13C NMR studies and chemical transformations. The mechanism and the stereochemical outcome of the reaction are discussed.
1991
Balsamo, A; Benvenuti, M; Lapucci, Annalina; Macchia, B; Nencetti, Susanna; Rossello, Armando; Macchia, F; Domiano, P; Dradi, E.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/173730
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