A C-C bonded 5,6-fused bicyclic energetic molecule: exploring an advanced energetic compound with improved performance

Chemical Communications : Chem Comm
Yongxing TangJean'ne M Shreeve

Abstract

A C-C bonded amino-nitro pyrazole (7) and its ring-expansion product (9) have been synthesized and characterized. The synthetic route to 9 proceeds in several steps from the commercial substrate diethyl oxalate and acetone. The process was found to be straightforward, practical and easily scalable. Both of these structures were confirmed by single crystal X-ray diffraction. Compound 9 with a high density (1.85 g cm-3) at room temperature, excellent thermal stability (Td: 315 °C), good detonation performance and low sensitivity to impact and friction has potential as a high-temperature energetic material.

References

Jun 18, 2010·Journal of Hazardous Materials·Veera M BodduR Damavarapu
Aug 16, 2011·Chemical Reviews·Haixiang Gao, Jean'ne M Shreeve
Sep 9, 2011·Angewandte Chemie·Onas Bolton, Adam J Matzger
Apr 5, 2013·Angewandte Chemie·Yongxing TangGuangbin Cheng
Oct 21, 2015·Angewandte Chemie·David E ChavezDamon A Parrish
Dec 17, 2015·Journal of the American Chemical Society·Yongxing TangJean'ne M Shreeve
Jun 9, 2016·Chemical Communications : Chem Comm·Chunlin HeJean'ne M Shreeve
Nov 20, 2016·Chemistry : a European Journal·Dheeraj KumarJean'ne M Shreeve
Nov 20, 2016·Angewandte Chemie·Davin G PierceyDamon A Parrish
Nov 26, 2016·Angewandte Chemie·Dennis FischerTomasz G Witkowski
Aug 5, 2017·Nature Communications·Wenquan ZhangQinghua Zhang
Sep 15, 2017·Journal of the American Chemical Society·Yongxing TangJean'ne M Shreeve
Oct 19, 2017·ACS Applied Materials & Interfaces·Qianyou WangLi Yang
Aug 4, 2018·Chemical Communications : Chem Comm·Chao YanQinghua Zhang

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Citations

Sep 19, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Yongxing TangJean'ne M Shreeve
Dec 12, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Chengming BianZhongliang Xiao
Aug 6, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Shijie ZhangKaichang Kou
Aug 6, 2021·The Journal of Organic Chemistry·Kento Iwai, Nagatoshi Nishiwaki
Mar 28, 2019·Organic Letters·Yongxing TangJean'ne M Shreeve
Oct 4, 2019·Organic Letters·Yongxing TangJean'ne M Shreeve

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Methods Mentioned

BETA
X-ray
NMR

Software Mentioned

Gaussion03
EXPLO5

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