T. Lemek, G. Groszek, P. Cmoch
Aug 1, 2008
Citations
0
Influential Citations
6
Citations
Journal
European Journal of Organic Chemistry
Abstract
1,1,1-Trifluoro-N-[oxido(phenyl)(trifluoromethyl)-λ4-sulfanylidene]methanesulfonamide reacts with carbanions bearing a leaving group to give vicarious nucleophilic substitution (VNS) of hydrogen products with moderate yields. This is the first example of the VNS process at a benzene ring activated by an electron-withdrawing group other than a nitro group. The orientation of the substitution is exclusively para. Findings open a large possibility for exploration of the scope of the VNS reaction on to compounds activated with sulfur-based electron-withdrawing groups. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)