Engaging DBFO As A C1N1 “two-atom Synthon” In [3 + 2 ...

Engaging DBFO as a C1N1 “two-atom synthon” in [3 + 2] cycloaddition reaction: synthesis of the energetic material 5-azidotetrazolate 1N-oxide†

Yong Hu,a Xiao-Jun Wang,a Wen-Shuai Dong,a Yu-Fan Bi,a Zu-Jia Lu,a Wen-Li Cao,a Jian-Guo Zhang, *a Qi Zhang b and Dong Chenb Author affiliations

* Corresponding authors

a State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, P. R. China E-mail: [email protected]

b Institute of Chemical Materials, China Academy of Engineering Physics, Mianyang, Sichuan 621900, China

Abstract

We report a formal [3 + 2] annulation of dibromoformaloxime (DBFO) and sodium azide for the synthesis of tetrazole-based energetic materials. Several energetic salts were prepared and fully characterized by X-ray diffraction, Raman spectroscopy, multinuclear NMR spectroscopy, elemental analysis, differential scanning calorimetry (DSC) and impact and friction sensitivity testing. The heat of formation of nitrogen-rich salts 8 and 9 was calculated by experiments, and detonation parameters were estimated using the EXPLO5 software. This is the first example of using DBFO as a unique C1N1 “two-atom synthon” in the synthesis of tetrazoles. Furthermore, this reaction not only unlocks a different strategy for 5-azidotetrazole synthesis, but also exploits a new reactivity of DBFO.

• This article is part of the themed collection: 2021 Organic Chemistry Frontiers HOT articles

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