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

Hartdegen, Vera A.; Hofmayer, Maximilian S.; Karaghiosoff, Konstantin and Klapötke, Thomas M. (2016): Synthesis and characterization of allyl- and vinyl-substituted 1,2-bis(tetrazolo)ethanes as polymeric precursors. In: Zeitschrift für Naturforschung Section B - A Journal of Chemical Sciences, Vol. 71, No. 12: pp. 1199-1209

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 degrees C and 230 degrees 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.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0932-0776
• Alliance/National Licence: This publication is with permission of the rights owner freely accessible due to an Alliance licence and a national licence (funded by the DFG, German Research Foundation) respectively.
• Language: English