Vinyl-λ3-iodanes act as efficient sulfur atom acceptors: vinylic SN2-based strategy for conversion of tertiary thioamides to amides
Literature Information
Masahito Ochiai, Shinji Yamamoto
Exposure of tertiary thioamides to (E)-1-hexenyl(phenyl)-λ3-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).
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