RATE ENHANCEMENT IN THE REDUCTION OF (2,3)-ALPHA-METHYLENEPENAM AND (2,3)-BETA-METHYLENEPENAM BETA-SULFOXIDES

The ease of reduction of (2,3)-alpha-methylenepenam beta-sulfoxides, ( 2,3)-beta-methylenepenam beta-sulfoxides and bicyclic penam beta-sulfo xides to the corresponding sulfides, using potassium iodide and triflu oroacetic anhydride in acetone or N,N-dimethylformamide, was measured. The results indicate that in general the rate of reduction of both (2 ,3)-alpha- and (2,3)-beta-methylenepenam beta-sulfoxides is several or ders of magnitude greater than the rate of reduction of bicyclic penam beta-sulfoxides. A mechanistic explanation to account for this observ ation is advanced. (C) 1998 Elsevier Science Ltd. All rights reserved.