51392-39-3Relevant articles and documents
Secondary Reactions of Sulfenes from Sulfonyl Chlorides and Tertiary Amines, 1. - On the Competing Formation of Sulfene-Trialkylamine S,N- and C,N-Adducts
Opitz, Guenter,Rieth, Karlheinz,Ehlis, Thomas
, p. 1563 - 1569 (2007/10/02)
Phenylmethanesulfonyl chloride (1 a) reacts with an excess oif triethylamine in acetonitrile solution at -40 deg C to give stilbene episulfone (9 a, 95percent) via the phenylsulfene-triethylamine S,N-adduct 5 ah.With trimethylamine and quinuclidine the yield of stilbene is reduced by the additional formation of (benzylsulfonyl)phenylsulfene-amine S,N-adducts 11 ag and 11 ae and C,N-adducts 15 ag and 15 ae which was proven by reaction with dimethylamine to 16 and by hydrolysis to 17-19, respectively. 1 d reacts with triethylamine yielding 94percent of α-chloro sulfones 4 d and 6 d via pentamethylenesulfene-triethylamine S,N-adduct 5 dh, with trimethylamine, however, C,N-adduct 12 dg is obtained which is easily oxidized to 20 dg (47percent).The air-sensitive dimethylsulfene-trimethylamine C,N-adduct 12 cg was isolated and characterized.