Phenol ring nitration induced by the unprecedented reduction of the Cu(ii) centre by nitrogen dioxide

Abstract

Nitrogen dioxide (˙NO₂) induces tyrosine nitration through a radical mechanism in biological systems. Two copper(II) complexes, 1 and 2, with ligands L₁ and L₂ [L₁ = 2,4-di-tert-butyl-6-(((2-(dimethylamino)ethyl)(isopropyl)amino)methyl)phenol; L₂ = 6,6′-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(2,4-di-tert-butylphenol)], respectively, have been made to react with ˙NO₂. In both cases, the reduction of the copper(II) center was observed in the presence of ˙NO₂ which induces phenol ring nitration through nitronium ion (NO₂⁺) formation.