CLEAVAGE OF SULFONAMIDES WITH PHENYLDIMETHYLSILYLLITHIUM

The toluene-p-sulfonamides of secondary amines and indoles are cleaved by treatment with phenyldimethylsilyllithium to give the secondary am ines. Aziridine toluene-p-sulfonamides, however, are opened by attack of the silyllithium reagent on carbon to give beta-silylethyl sulfonam ides, The aziridine toluene-p-sulfonamide 22 derived from norbornene i s different in giving the [dimethyl(phenyl)silyl]-4-methylbenzenesulfo namide 23 of exo-norbornylamine. The aziridine toluene-p-sulfonamides 26, 28 and 30, derived from methyl cinnamate, methyl acrylate and cinn amyl acetate, are also anomalous, giving 3-[N-(p-tolylsulfonyl)amino]- 3-phenylpropionic acid 27, lylsulfonyl)amino]propionyl)dimethyl(phenyl )silane 29 and trans-cinnamyl alcohol 31, respectively, each derived b y opening of the aziridine ring followed by loss of the silyl group.