A novel reaction of N-phenylthiocaprolactam: The α-sulfenylation of ketones under mild conditions

Article abstract of DOI:10.1016/S0040-4039(97)00288-8

N-phenylthiocaprolactam (2) reacts with the enolate anions of aliphatic, aromatic or cyclic ketone 1a-e, to give the corresponding α-phenylthioketones 3a-e. This reaction proceeds with high yields of monosulphenylation (80-97%) in DMSO under mild conditions (potassium ter-butoxide, 25°C, 10 min).