115022-91-8Relevant articles and documents
Boron Trifluoride-Promoted Reaction of Benzenesulphenanilides with Alkenes in Acetonitrile and Benzonitrile: Amidino- and Amido-sulphenylation of Alkenes
Benati, Luisa,Montevecchi, P. Carlo,Spagnolo, Piero
, p. 2815 - 2818 (2007/10/02)
Benzenesulphenanilides (1) react at room temperature with alkenes in acetonitrile or benzonitrile in the presence of boron trifluoride-diethyl ether to give amidino sulphides (5; R=Me, Ph) in fair to good yields together with varying amounts of amido sulphides (7; R=Me, Ph) and arylamino sulphides (4), whereas at 100 deg C and in the presence of water 4'-nitrobenzenesulphenanilide affords amido sulphides (7; R=Me, Ph) as the main products.With cyclohexene a high selectivity for trans-addition is observed.With terminal alkenes the terminal sulphides are produced with high regioselectivity.The findings are consistent with a mechanism involving intermediacy of episulphonium ions (3) which result from alkene attack at the sulphur atom of an anilide-BF3 complex.