Stereoselective synthesis of (Z)-enethiols and their derivatives: vinylic S(N)2 reaction of (E)-alkenyl(phenyl)-lambda3-iodanes with thioamides

[reaction: see text]. Exposure of (E)-beta-alkylvinyl(phenyl)-lambda3-iodanes to thioamides in dichloromethane at room temperature was found to result in a bimolecular nucleophilic substitution (S(N)2) at the vinylic carbon atom to give inverted (Z)-enethiols and/or (Z)-S-vinylthioimidonium salts. Vinylic S(N)2 reactions with thioureas are also discussed.