Propellants Explosives Pyrotechnics, Vol.23, No.3, 142-149, 1998
Dinitro trifurazins with oxy, azo, azoxy bridges
The search of the new low-melting high energetic material, which match the performance of TNAZ and more available, is the barest necessity. The syntheses of several novel zero-hydrogen but nitrogen and oxygen rich high energetic heterocycles, such as bridged nitrofurazans, were undertaken to test the hypothesis that accumulate furazan ring in such molecule could effectively serve in construction of energetically interesting materials. Eight dinitro trifurazans were synthesized and tested. The series of compounds was prepared in three-five stages from the 3,4-diaminofurazan (10). Oxy bridge was formed by utilizing hydroxyfurazans as nucleophiles. Azo bridge was prepared by oxidizing coupling of amino groups with KMnO4 in acid medium. Transformation of azo bridge to azoxy one was accomplished by mixture of (NH4)(2)S2O8 and oleum. The set of trifurazans represents a new class of low-melting high energetic material which are among the most potent CxHyNzOx-explosives known. The isomeric diazoxyfurazans, (28), (29), and (30), differ dramatically in their properties. Liquid diazoxy compound (28) has density of 1.8 g/cm(3) and is reach a record figure for CxHyNzOw-oil known.