Nitration of nonactivated arenes with a ternary system NO–NO2–O2. Mechanistic implications of the Kyodai-nitration

Abstract

The ternary mixture NO–NO₂–O₂ has been found to be more effective than the binary mixture NO₂–O₂ as a nitrating agent for nonactivated arenes, such as toluene and chlorobenzene; the results may be rationalized in terms of an initial electron transfer mechanism in which nitrogen trioxide, formed from nitrogen monoxide and dioxygen, oxidizes the arene to its radical cation.