Explosive Meisenheimer complexes formed by addition of nucleophilic reagents to 4,6-dinitrobenzofurazan 1-oxide

Abstract

The reaction between 4,6-dinitrobenzofurazan 1-oxide (1) and a number of nucleophilic oxygen and nitrogen reagents has been studied. The exceptional electrophilic power of (1) leads to formation of 1 : 1 Meisenheimer complexes as the general reaction observed. Ammonia and hydrazine also form bis-adducts in the presence of excess (1). All the adducts were isolated as stable, but highly explosive, cystalline solids, and have been characterized by micro-analysis and spectroscopy. The adducts from N₃^- and I^- have been observed spectroscopically but not isolated. The monomethoxy adduct (8) undergoes a novel internal oxidation-reduction to form a gem-dimethoxybenzofurazan complex(6).