title: Vinyl-lambda 3-iodanes act as efficient sulfur atom acceptors: vinylic SN2-based strategy for conversion of tertiary thioamides to amides.
abstract: Exposure of tertiary thioamides to (E)-1-hexenyl(phenyl)-lambda 3-iodane results in vinylic SN2 reaction to give the inverted (Z)-S-vinylthioimidonium salts, which under alkaline hydrolysis (Na2CO3 or K2CO3) selectively afford amides, while (Z)-S-vinyl thioesters are obtained in high yields via the hydrolysis under acidic conditions (HCl).
authors.affiliation: Faculty of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan. mochiai@ph2.tokushima-u.ac.jp
authors.forename: Masahito
authors.initials: M
authors.lastname: Ochiai
authors.forename: Shinji
authors.initials: S
authors.lastname: Yamamoto