The reaction of N-phenylsulfonimidoyl chloride with trimethylsilylethene. A new route to 2-alkenylanilines

Article abstract of DOI:10.1016/S0040-4020(98)00591-2

N-Phenylsulfonimidoyl chloride reacts with trimethylsilylethene in the presence of aluminum chloride to give two product benzothiazines, one of which has been desilylated. The silylated benzothiazine can be deprotonated and alkylated, sometimes with very high diastereocontrol. Upon treatment with fluoride, these silylated benzothiazines undergo desilylation with concomitant cleavage of the carbon-sulfur bond to give 2- alkenylsulfinanilides which can be hydrolyzed to the corresponding anilines.