Cleavage of sulfonamides with phenyldimethylsilyllithium

Abstract

The toluene-p-sulfonamides of secondary amines and indoles are cleaved by treatment with phenyldimethylsilyllithium to give the secondary amines. Aziridine toluene-p-sulfonamides, however, are opened by attack of the silyllithium reagent on carbon to give β-silylethyl sulfonamides. The aziridine toluene-p-sulfonamide 22 derived from norbornene is different in giving the 2-[dimethyl(phenyl)silyl]-4-methylbenzenesulfonamide 23 of exo-norbornylamine. The aziridine toluene-p-sulfonamides 26, 28 and 30, derived from methyl cinnamate, methyl acrylate and cinnamyl acetate, are also anomalous, giving 3-[ N-( p-tolylsulfonyl)amino]-3-phenylpropionic acid 27, {3-[ N-( p-tolylsulfonyl)amino]propionyl}dimethyl(phenyl)silane 29 and trans-cinnamyl alcohol 31, respectively, each derived by opening of the aziridine ring followed by loss of the silyl group.

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