期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2018, 期 19, 页码 2273-2276出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800347
关键词
Energetic materials; Nitrogen heterocycles; Azo coupling reaction; Azido group; Imidazole
资金
- Office of Naval Research [NOOO14-12-1-0536]
- Defense Threat Reduction Agency [HDTRA1-11-1-0034]
- M. J. Murdock Charitable Trust [2014120: MNL:11/20/2014]
Despite the high potential of the azo-coupled fused tricyclic 1,2,3,4-tetrazine ring system in energetic materials, there are only very limited examples of such a scaffold. The oxidation of di-N-amino compound 1 with tert-butyl hypochlorite (tBuOCl) gives rise to the unexpected chloro-substituted compound 2, which behaves as a precursor to the structurally attractive diazido/nitro-substituted fused tricyclic 1,2,3,4-tetrazine 3. The structure is well characterized and is supported by single-crystal X-ray diffraction. Compound 3 was found to be a highly energetic and sensitive explosive.
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