ISSN:
0009-2940
Keywords:
Sulfene-amine adducts
;
Amine-sulfene adducts
;
2-Trimethylammonio-2-propanesulfinate
;
Episulfones
;
Sulfones, α-chloro-
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Secondary Reactions of Sulfenes from Sulfonyl Chlorides and Tertiary Amines, 1. - On the Competing Formation of Sulfene - Trialkylamine S,N- and C,N-AdductsPhenylmethanesulfonyl chloride (1a) reacts with an excess of triethylamine in acetonitrile solution at -40°C to give stilbene episulfone (9a, 95%) via the phenylsulfene-triethylamine S,N-adduct 1ah. With trimethylamine and quinuclidine the yield of stilbene is reduced by the additional formation of (benzylsulfonyl)phenylsulfene-amines S,N-adducts 11ag and 11ae and C,N-adducts 15ag and 15ae which was proven by reaction with dimethylamine to 16 and by hydrolysis to 17-19, respectively. 1d reacts with triethylamine yielding 94% of α-chloro sulfones 4s and 6d via pentamethylenesulfene-triethylamine S,N-adduct 5dh, with trimethylamine, however, C,N-adduct 12dg is obtained which is easily oxidized to 20dg (47%). The air-sensitive dimethylsulfene-trimethylamine C,N-adduct 12cg was isolated and characterized.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19901230717
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