89024-26-0Relevant articles and documents
Formation of β-lactams from 3-phenylthiopropionamide derivatives. A possible model for penicillin biosynthesis
Beckwith,Easton
, p. 3995 - 4001 (1983)
The Cu-catalysed reaction of the substituted 3-phenylthiopropianamide with di-t-butyl peroxide gives the β-lactam via oxidative cyclisation of the α-thioalkyl radical. Similar reactions of the propionamides with t-butyl perbenzoate give benzoates which can be readily converted into the β-lactams, but neither β-lactams nor benzoates can be obtained from the thiazepines. Dimethyl disulfide is benzoyloxylated on treatment with t-butyl perbenzoate. The relevance of these results to penicillin biosynthesis is discussed.
