INTERCONVERSION OF THE THIAZINE AND THIAZOLIDINE SYSTEM OF β-LACTAM ANTIBIOTICS. ELECTROCHEMICAL CLEAVAGE OF KAMIYA'S DISULPHIDE PROMOTED BY BROMIDE ION

Article abstract of DOI:10.1016/S0040-4039(00)87514-0

A new transformation of Kamiya's disulphide (1) into the bromopenam derivative (4) has been carried out by eletrolyzing the disulphide (1) in protic solvents in the presence of Me4NBr.The transformation occurs through an intermediate episulphonium-bromide ion pair in which the bromide appears to be tightly linked to the sulphur.