Disubstituted Azidotetrazoles as Energetic Compounds

作者：Abe Takashi; Joo Young Hyuk; Tao Guo Hong; Twamley Brendan; Shreeve Jean'ne M^*

来源：Chemistry - A European Journal, 2009, 15(16): 4102-4110.

DOI：10.1002/chem.200900034

• azidotetrazoles
• C-F activation
• energetic materials
• heterocycles
• high-nitrogen compounds

Disubstituted azidotetrazoles are synthesized by the base-catalyzed activation of the C-F bond in the trifluoromethylazo-substituted cyclic and acyclic alkanes. From the reaction of trans-1,4-bis(trifluoromethylazo)cyclohexane with four equivalents of NaN(3), N,N'-bis(5-azido-1H-tetrazol-1-yl)-1,4-diiminocyclohexane was formed in good yield. While, from the similar reaction using cis/trans-1,2-bis(trifluoromethylazo) cyclohexane, (5-azido-1H-tetrazol-1-yl)-[6-(5-azido-1H-tetrazol-1-ylimino)cyclohexenyl]amine was formed as the principal product. The structure of these new disubstituted azidotetrazoles was determined by crystal structure analysis as well as NMR and IR spectroscopy. In a similar fashion, from three trifluoromethylazo-substituted acyclic alkanes, corresponding alkyl-bridged N,N'bis(5-azido-1H-tetrazol-1-yl)diiminoalkanes were obtained. For example, from 1,2-bis(trifluoromethylazo)ethane, N,N'bis(5-azido-1H-tetrazol-1-yl)-1,2-diiminoethane was obtained in 75% yield. Heats of formation, detonation pressures, detonation velocities, and impact sensitivities are reported for these new disubstituted azidotetrazoles.

• 出版日期2009