89024-29-3Relevant articles and documents
Benzoyloxymethyl p-toluenethiosulfonate: A crystalline, stable synthetic equivalent for+CH2S+
Kabir, S. M. Humayun,Langler, Richard F.
, p. 362 - 367 (2007/10/03)
Benzoyloxymethyl p-toluenethiosulfonate has been developed as a reagent for the one-pot preparation of α-sulfide disulfides and the corresponding symmetrical bissulfide disulfides. The reagent is effective for systems bearing terminal aryl groups. CSIRO 2005.
Formation of β-lactams from 3-phenylthiopropionamide derivatives. A possible model for penicillin biosynthesis
Beckwith,Easton
, p. 3995 - 4001 (2007/10/02)
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.