Stereoselective Synthesis of (Z)-Enethiols and Their Derivatives: Vinylic SN2 Reaction of (E)-Alkenyl(phenyl)-λ3-iodanes with Thioamides
摘要:
[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.