Stereoselective synthesis of (Z)-enethiols and their derivatives:: Vinylic SN2 reaction of (E)-alkenyl(phenyl)-λ3-iodanes with thioamides

[GRAPHICS] Exposure of (E)-beta -alkylvinyl(phenyl)-lambda (3)-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 SN2 reactions with thioureas are also discussed.