Jump to main content
Jump to site search

Issue 20, 2017
Previous Article Next Article

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

Author affiliations

Abstract

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

Graphical abstract: Synthesis of 5,5′-azoxybistetrazole via nitration and de-oxygen rearrangement of triazene

Back to tab navigation

Supplementary files

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., 2017,41, 11512-11516
  •   Request permissions

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

    Q. Wang, T. Lu, C. Wang, G. Fan, H. Yin and F. Chen, New J. Chem., 2017, 41, 11512
    DOI: 10.1039/C7NJ02724A

Search articles by author

Spotlight

Advertisements