Abstract
At heating of 2-(2-azido-3,5-dinitrophenyl)-2H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 4,6-dioxide in toluene at 110 °C, the azido group interacts mainly with the neighboring nitro group and to a lesser extent with the neighboring 1,2,3-triazole ring, resulting in 2-(6-nitrobenzofuroxan-4-yl)-2H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 4,6-dioxide (2) in 68% yield, as well as 8,10-dinitro-5,11-dehydro-5H,11H-[1,2,3,4]tetrazino[5′,6′:4,5]-[1,2,3]triazolo[2,1-a][1,2,3]benzotriazole 1,3-dioxide and 8,10-dinitro-5,11-dehydro-5H,11H-[1,2,3,4]tetrazino[5′,6′:4,5][1,2,3]triazolo[2,1-a][1,2,3]benzotriazole 2,4-dioxide in 5% yields respectively. Furoxan 2 may be of interest as an energetic compound due to the combination of good thermal stability, positive estimated enthalpy of formation (ΔH°f = 1005 kJ mol−1) and optimal density.
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This work was financially supported by the Russian Academy of Sciences (program of the Presidium of the Russian Academy of Sciences No. 22).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0739–0741, April, 2020.
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Shvets, A.O., Konnov, A.A., Klenov, M.S. et al. Synthesis of 2-(6-nitrobenzofuroxan-4-yl)-2H-[1,2,3]triazolo-[4,5-e][1,2,3,4]tetrazine 4,6-dioxide. Russ Chem Bull 69, 739–741 (2020). https://doi.org/10.1007/s11172-020-2826-3
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DOI: https://doi.org/10.1007/s11172-020-2826-3