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Synthesis of 5,5'-azoxybistetrazole via nitration and de-oxygen rearrangement of triazene

Abstract

An efficient approach of 5,5'-azoxybistetrazoles has been achieved by treatment of tetrazolyl triazenes using fuming nitric acid and acetic anhydride in a two-step one-pot reaction. The 5,5'-azoxybistetrazole is proposed to be formed via a nitroso triazene intermediate generated from tetrazolyl triazene by nitration and deoxygen rearrangement. All compounds were fully characterized using IR, 1H and 13C NMR spectroscopy, and HRMS, and, in the case of 2,2'-dimethyl-5,5'-azoxybistetrazole (2a) together with single crystal X-ray structuring and 15N NMR spectroscopy. Calculations predict 2f has a detonation velocity of 8066 m s‒1 and a detonation pressure of 25.8 GPa.

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Publication details

The article was received on 25 Jul 2017, accepted on 10 Sep 2017 and first published on 11 Sep 2017


Article type: Letter
DOI: 10.1039/C7NJ02724A
Citation: New J. Chem., 2017, Accepted Manuscript
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    Synthesis of 5,5'-azoxybistetrazole via nitration and de-oxygen rearrangement of triazene

    F. Chen, Q. Wang, T. Lu, C. Wang, G. Fan and H. Yin, New J. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7NJ02724A

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