cine-Substitution of the nitro group in 2,4-disubstituted nitroarenes with carbanions of aryl alkyl sulfones

• Published in: Tetrahedron letters Vol. 45; no. 16; pp. 3193 - 3195
• Main Authors: Błażej, Sylwia, Kwast, Andrzej, Mąkosza, Mieczysław
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 12.04.2004; Elsevier
• Subjects: Carbanions; Chemistry; Chemistry, Organic; cine-Substitution; Nitroarenes; Physical Sciences; Science & Technology; Sulfones; Carbanions; cine-Substitution; Nitroarenes; Sulfones; VICARIOUS NUCLEOPHILIC-SUBSTITUTION; HYDROGEN; nitroarenes; sulfones; carbanions; CONDENSATION; DERIVATIVES; cine-substitution

Graphic Rapid protonation of short lived σ H adducts of carbanions of aryl alkyl sulfones to 2,4-disubstituted nitrobenzenes results in elimination of nitrous acid giving 1,3,5-trisubstituted benzenes as products of cine-substitution of the nitro group.