Site-Selective Oxidative Coupling Reaction of Diamines toward Aminoazo Compounds.

A selective oxidative coupling reaction of a diamine containing both - and -NH was achieved using acidic potassium permanganate as the coupling reagent. The reaction conditions were optimized, and the reaction selectivity was illustrated by quantum calculations. Furthermore, the azo-coupled product was derivatized to four nitroamine energetic materials with excellent detonation performances.