Synthesis and characterization of allyl- and vinylsubstituted 1,2-bis(tetrazolo)ethanes as polymeric precursors

Abstract

On the basis of 1,2-bis(5-tetrazolo)ethane (BTE) the corresponding twofold vinyl and allyl N-substituted derivatives were synthesized using 1,2-dibromoethane and allyl bromide, respectively. The compounds were obtained as two different constitutional isomers. Both species were analyzed using NMR and IR spectroscopy, elemental analysis, as well as mass spectrometry. In the case of the diallyl bistetrazoles, the two isomers were characterized using 2D NMR spectroscopy. The synthesis of the divinyl compounds gave crystals of the 2,2'-N-substituted isomer, which were analyzed by single-crystal X-ray diffraction. The thermal stability of the compounds was determined using differential scanning calorimetry (DSC) and gave decomposition temperatures around 190°C and 230°C. For the investigation of the inherent energetic potential, sensitivities toward physical stimuli and detonation parameters were determined. The compounds turned out to be insensitive toward friction and impact and possess moderate energetic properties.