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)
✍ Scribed by Ganesan Subramanian; Mark L. Trudell; Joseph H. Boyer
- Publisher
- John Wiley and Sons
- Year
- 1995
- Tongue
- English
- Weight
- 489 KB
- Volume
- 6
- Category
- Article
- ISSN
- 1042-7163
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✦ Synopsis
Abstract
A reaction between 2, 8‐dichloro‐4, 10‐dinitro‐5, 11‐dehydro‐5H, 11H‐benzotriazolo[2, 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‐benzotriazolo[2, 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‐benzotriazolo[2, 1‐a]‐benzotriazole 16. Nitration (100% HNO~3~, CF~3~SO~3~H) converted compound 16 to the 3,4,10‐trinitro derivative 17, whereas a similar nitration (100% HNO~3~, FSO~3~H) gave the title compound BTBB, an insensitive high‐energy, high‐density (d 2.03 g/cc) molecule. © 1995 John Wiley & Sons, Inc.