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Vicarious Nucleophilic Substitutions of Hydrogen in 1,1,1‐Trifluoro‐ N ‐[oxido(phenyl)(trifluoromethyl)‐λ 4 ‐sulfanylidene]methanesulfonamide
Author(s) -
Lemek Tadeusz,
Groszek Grażyna,
Cmoch Piotr
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800390
Subject(s) - chemistry , trifluoromethyl , carbanion , nitro , nucleophile , medicinal chemistry , polar effect , benzene , nucleophilic substitution , ring (chemistry) , hydrogen , nucleophilic aromatic substitution , leaving group , stereochemistry , organic chemistry , catalysis , alkyl
1,1,1‐Trifluoro‐ N ‐[oxido(phenyl)(trifluoromethyl)‐λ 4 ‐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)