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Issue 23, 2002
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Vinyl-λ3-iodanes act as efficient sulfur atom acceptors: vinylic SN2-based strategy for conversion of tertiary thioamides to amides

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Abstract

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).

Graphical abstract: Vinyl-λ3-iodanes act as efficient sulfur atom acceptors: vinylic SN2-based strategy for conversion of tertiary thioamides to amides

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Publication details

The article was received on 18 Sep 2002, accepted on 08 Oct 2002 and first published on 24 Oct 2002


Article type: Communication
DOI: 10.1039/B209097J
Chem. Commun., 2002, 2802-2803

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    Vinyl-λ3-iodanes act as efficient sulfur atom acceptors: vinylic SN2-based strategy for conversion of tertiary thioamides to amides

    M. Ochiai and S. Yamamoto, Chem. Commun., 2002, 2802
    DOI: 10.1039/B209097J

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