DENSE ENERGETIC COMPOUNDS OF C, H, N, AND O ATOMS .4. NITRO AND AZIDOFURAZAN DERIVATIVES

Both diaminofurazan 5 (DAF) and diaminoazofurazan 6 (DAAF) were conver ted to 5-(4-amino-1,2,5-oxadiazol-3-yl)-1 H-[1,2,3]triazolo[4,5-c][1,2 ,5]oxadiazolium inner salt 8 (AMOTO) 25 and 98%) in oxidations with io dobenzene diacetate and to dinitroazoxyfurazan 13 (DNAF) (4 and 15%) i n oxidations with a mixture of ammonium persulfate and hydrogen peroxi de in concentrated sulfuric acid. The intermediacy of diaminoazoxyfura zan 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]oxadiazolium]bis(inner salt) 10. Diazidofurazan 19 ( tentative assignment) was obtained from DAF 5 by tetrazotization follo wed by treatment with sodium azide. Aminoazido-azofurazan 16 was obtai ned from diazotized DAAF by treatment with sodium azide and was conver ted to AMOTO 8 by elimination of nitrogen at 25 degrees C. Similar tre atment converted tetrazolized DAAF to diazidoazofurazan 9 and 5-(4-azi do-1,2,5-oxadiazol-3-yl) - 1H -[1,2,3]-triazolo[4,5-c][1,2,5]-oxadiazo lium inner salt 15 (AZOTO) after evolution of nitrogen. Aminofurazan-2 -ONN-azoxyazidofurazan 17 (AAAF) was obtained from diazotized diaminoa zoxyfurazan 7 by treatment with sodium azide. Excellent calculated det onation properties were obtained for DNAF 13, AZOTO 15, and AAAF 17.