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Issue 9, 2017
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A furazan-fused pyrazole N-oxide via unusual cyclization

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Abstract

6-Nitro-pyrazolo[3,4-c]furazanate 5-oxide, a new fused anion with high energy, was designed and synthesized via an unusual intramolecular cyclization reaction of 3 by using a mixture of 100% nitric acid and trifluoroacetic anhydride followed by KI reduction. The potassium (6) and nitrogen-rich energetic (9–16) salts were prepared, and fully characterized by IR and multinuclear NMR spectroscopy, elemental analysis, and single-crystal X-ray structuring, 6, 9 and 16. Hydroxylammonium salt (10) has excellent detonation performance but high sensitivity, while 13 and 16 have detonation velocities comparable to 1,3,5-trinitro-1,3,5-triazinane (RDX), which suggests they may have potential application as green primary or secondary explosives.

Graphical abstract: A furazan-fused pyrazole N-oxide via unusual cyclization

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Article information


Submitted
25 Jan 2017
Accepted
08 Feb 2017
First published
09 Feb 2017

J. Mater. Chem. A, 2017,5, 4314-4319
Article type
Communication

A furazan-fused pyrazole N-oxide via unusual cyclization

Y. Tang, C. He and J. M. Shreeve, J. Mater. Chem. A, 2017, 5, 4314
DOI: 10.1039/C7TA00846E

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