Nitration of nonactivated arenes with a ternary system NO–NO 2 –O 2 . Mechanistic implications of the Kyodai-nitration

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.