期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 88, 期 7, 页码 4301-4308出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02879
关键词
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In this study, the nitration of NH on the 1,2,3-triazole ring and the synthesis of nitrogen-rich energetic compounds were reported. A novel fused nitrogen-rich heterocycle was obtained, showing high nitrogen content and good thermal stability. The compounds synthesized exhibited high detonation velocity and detonation pressure.
Here, we report the nitration of NH on the 1,2,3-triazole ring and the synthesis of several nitrogen-rich energetic compounds based on key intermediate 4-azido-5(chlorodinitromethyl)-2-nitro-2H-1,2,3-triazole (5). Starting from 4-amino-1H-1,2,3-triazole-5carbonitrile (1), we successfully constructed compound 5 through four steps. Subsequently, the dechlorination of compound 5 gave potassium 4-azido-5-(dinitromethyl)-2H-1,2,3-triazole (6) (IS = 1 J, vD = 8802 m s(-1)). Additionally, diammonium (8) and dihydrazinium (9) salts based on 4-azido-5-(dinitromethyl)-2H-1,2,3-triazole were also successfully synthesized and characterized. A novel fused nitrogen-rich heterocycle, namely, 6H-[1,2,3]triazolo[4,5-d][1,2,3] triazine-6,7-diamine (10), was surprisingly obtained, which has a high nitrogen content of 73.66% and shows good thermal stability (Tdec = 203 degrees C) and insensitivity to mechanical stimuli, while the detonation velocity (vD) and detonation pressure (P) reach 8421 m s(-1) and 26.0 GPa, respectively.
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