BORON TRIFLUORIDE PROMOTED REACTION OF BENZENESULPHENANILIDES WITH ALKENES

Article abstract of DOI:10.1016/S0040-4020(01)87520-7

The boron trifluoride-promoted reaction of a series of 3'- and 4'-substituted benzenesulphenanilides (1) with various alkenes has been investigated as a potential synthetic route to arylaminosulphides.The benzenesulphenanilides (1) investigated generally afford arylaminosulphenylation adducts in fair to good yields except for the methoxy-substituted anilides (1e and f), which largely lead to decomposition products under comparable conditions.In all cases examined, the addition proceeds with trans-stereospecificity and, with terminal alkenes, leads regioselectively to the exclusive (or predominant) formation of the terminal sulphides.The findings are interpreted by assuming that boron trifluoride transforms the sluggish benzenesulphenanilides (1) into reactive electrophilic species, which can undergo nucleophilic attack at sulphur by an alkene, presumably affording episulphonium-borate ion-pair intermediates, in competition with attack by another sulphenanilide unit.