Dense energetic compounds of carbon,hydrogen, nitrogen,and oxygen atoms. V. 1,2,7,8-bisfuroxano-3,4,9,10-tetranitro-5, 11-dehydro-5H, 11H-benzotriazolo[2, 1-a]benzotriazole (BTBB)

A reaction between 2, 8-dichloro-4, 10-dinitro-5, 11-dehydro-5H, 11H-benzotriazolo2, 1-a]-benzotriazole 8 and sodium azide in dimethyl sulfoxide produced 3, 9-diazido-4, 10-dinitro-5, 11-dehydro-5H, 11H-benzotriazolo 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-benzotriazolo2, 1-a]benzotriazole 11 that was subsequently nitrated to give the 2,8-dinitro derivative 12 . Similar nitration 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-benzotriazolo2, 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-density (d 2.03 g/cc) molecule. © 1995 John Wiley & Sons, Inc.