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First General Synthesis of (p-Nitroaryl)diarylmethanes via Vicarious Nucleophilic Substitution of Hydrogen.

Domenii publicaţii > Chimie + Tipuri publicaţii > Articol în revistã ştiinţificã

Autori: Katritzky, Alan R.; Toader, Dorin

Editorial: J. Org. Chem., 62(12), p.4137-4141, 1997.

Rezumat:

A general regiospecific method for the synthesis of (p-nitroaryl)diarylmethanes has been developed starting from diarylmethanols and 2- and/or 3-substituted nitrobenzenes. This utilizes the quant. condensation between benzotriazole and diarylmethanols under acidic catalysis and in the presence of perfluorocarbon fluids, followed by vicarious nucleophilic substitution of the resulting (diarylmethyl)benzotriazoles with nitrobenzenes in moderate to high yield. Oxidative nucleophilic substitution of hydrogen is obsd. as a side process. These vicarious nucleophilic substitutions complement Friedel-Crafts reactions for the synthesis of triarylmethanes.

Cuvinte cheie: organic chemistry