Issue 23, 2002
From the journal:

Chemical Communications

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

Masahito Ochiai*a  and  Shinji Yamamotoa  

* Corresponding authors

a Faculty of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima, Japan
E-mail: mochiai@ph2.tokushima-u.ac.jp
Fax: +81 88 633 9504
Tel: +81 88 633 7281

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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Article information

DOI
https://doi.org/10.1039/B209097J
Article type
Communication
Submitted
18 Sep 2002
Accepted
08 Oct 2002
First published
24 Oct 2002

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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