Toru Minami, Futoshi. Takimoto, Toshio Agawa
1975
Citations
0
Influential Citations
11
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
N-Sulfinylsulfonamides, 1a, b, reacted with ketenimines, 2, in ether to give the unstable [2+2] cycloadducts, 3-ylidene-1,2,4-thiadiazetidin-1-oxides, 3, which were then readily hydrolyzed to the N,N′’-disubstituted amidine derivative, 4, in good yields. The reaction of N-sulfinylmethanesulfonamide (1b) with diphenylketen-N-p-tolylimine (2d) at 130 °C gave the exchange product, N-sulfinyl-p-toluidine (5) in a 70% yield via the intermediate cycloadduct. In contrast to 2d, the reaction of N-sulfinyl-p-toluenesulfonamide (1a) and phenylethylketen-N-phenylimine (2f), under the same conditions, led to the formation of a mixture of N-phenyl-N′-p-toluenesulfonyl-2-phenyl-trans- (6a) and cis-2-butenoamidine (6b) in an 81% yield.