title: Stereoselective synthesis of (Z)-enethiols and their derivatives: vinylic S(N)2 reaction of (E)-alkenyl(phenyl)-lambda3-iodanes with thioamides.
abstract: [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.
authors.affiliation: Faculty of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan. mochiai@ph2.tokushima-u.ac.jp
authors.forename: M
authors.initials: M
authors.lastname: Ochiai
authors.forename: S
authors.initials: S
authors.lastname: Yamamoto
authors.forename: T
authors.initials: T
authors.lastname: Suefuji
authors.forename: D W
authors.initials: DW
authors.lastname: Chen