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Dense energetic compounds of C, H, N, and O atoms IV nitro and azidofurazan derivatives

1994; Wiley; Volume: 5; Issue: 5-6 Linguagem: Inglês

10.1002/hc.520050505

1098-1071

Ananthakrishnan Gunasekaran, Mark L. Trudell, Joseph H. Boyer,

Thermal and Kinetic Analysis

Abstract Both diaminofurazan 5 (DAF) and diaminoazofurazan 6 (DAAF) were converted to 5‐(4‐amino‐1,2,5‐oxadiazol‐3‐yl)‐1H‐[1,2,3]triazolo[4,5‐c][1,2,5]oxadiazol‐3‐yl‐1H‐[1,2,3]triazolo[4,5‐c][1,2,5]oxadiazolium inner salt 8 (AMOTO) (25 and 91%) in oxidations with iodobenzene diacetate and to dinitroazoxyfurazan 13 (DNAF) (4 and 15%) in oxidations with a mixture of ammonium persulfate and hydrogen peroxide in concentrated sulfuric acid. The intermediacy of diaminoazoxyfurazan 7 was supported by its conversion under similar treatment to DNAF (60%). Further oxidation by ammonium persulfate converted AMOTO 8 to 5,5′[azobis‐(1,2,5‐oxadiazole‐4,3 ‐ diyl)]bis[1H(1,2,3)triazolo ‐ [4,5‐c][1,2,5]oxadiazolium]bis(inner salt) 10 . Diazidofurazan 19 (tentative assignment) was obtained from DAF 5 by tetrazotization followed by treatment with sodium azide. Aminoazido‐azofurazan 16 was obtained from diazotized DAAF by treatment with sodium azide and was converted to AMOTO 8 by an elimination of nitrogen at 25°C. Similar treatment converted tetrazotized DAAF to diazidoazofurazan 9 and 5‐(4‐azido‐1,2,5‐oxadiazol‐3‐yl) ‐ 1H ‐[1,2,3]‐triazolo[4,5‐c][1,2,5]‐oxadiazolium inner salt 15 (AZOTO) after evolution of nitrogen. Aminofurazan‐2‐ONN‐azoxyazidofurazan 17 (AAAF) was obtained from diazotized diaminoazoxyfurazan 7 by treatment with sodium azide. Excellent calculated detonation properties were obtained for DNAF 13 , AZOTO 15 , and AAAF 17 .