Issue 11, 2021

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

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
23 janv. 2021
Accepted
07 mars 2021
First published
23 mars 2021

Org. Chem. Front., 2021,8, 2420-2428

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

Y. Hu, X. Wang, W. Dong, Y. Bi, Z. Lu, W. Cao, J. Zhang, Q. Zhang and D. Chen, Org. Chem. Front., 2021, 8, 2420 DOI: 10.1039/D1QO00123J

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