DENSE ENERGETIC COMPOUNDS OF CARBON, HYDROGEN, NITROGEN, AND OXYGEN-ATOMS .5. 1,2,7,8-BISFUROXANO-3,4,9,10 1-DEHYDRO-5H,11H-BENZOTRIAZOLO[2,1-A]BENZOTRIAZOLE (BTBB)

A reaction between 2, 8-dichloro-4, 10-dinitro-5, 11-dehydro-5H, 11H-b enzotriazolo[2, 1-a]-benzotriazole 8 and sodium azide in dimethyl sulf oxide produced 3, 9-diazido -4, 10-dinitro-5, 11-dehydro-5H, 11H-benzo triazolo [2, 1-a]benzotriazole 10 rather than the 2.8-diazido isomer 9 expected by direct displacement. Thermolytic elimination of nitrogen (2 moles) converted the dinitro diazide 10 to 3,4,9,10-bisfuroxano-5, 11-dehydro-5H, 11H-benzotriazolo[2, 1-a]benzotriazole 11 that was subs equently nitrated to give the 2, 8dinitro derivative 12. Similar nitra tion converted the dinitro diazide 9 to the trinitro 15 and tetranitro 14 derivatives: thermolysis of the latter gave 1,2,7,8-bisfuroxano-4, 10-dinitro-5, 11-dehydro-5H, 11H-benzotriazolo[2, 1-a]-benzotriazole 16. Nitration (100% HNO3, CF3SO3H) converted compound 16 to the 3,4,10 -trinitro derivative 17, whereas a similar nitration (100% HNO3, FSO3H ) gave the title compound BTBB, an insensitive high-energy, high-densi ty (d 2. 03 g/cc) molecule. (C) 1995 John Wiley & Sons, Inc.