Alkylation of nitroarenes with Grignard reagents via oxidative nucleophilic substitution of hydrogen

Alkylation of nitroarenes with Grignard reagents via oxidative nucleophilic substitution of hydrogen (ONSH) can be efficiently executed with potasium permanganate in liquid ammonia as an oxidative system for the sigma (H) adducts. The addition of RMgX to ArNO2 of stoichiometry 1:1 is accompanied with a redox process apparently of stoichiometry 2:1. Because of that, real stoichiometry of the reaction between nitroarenes and Grignard reagents is ca. 1:1.5. (C) 2001 Elsevier Science B.V. AH rights reserved.