Promising Energetic Asymmetric Bistetrazoles Synthesized via Sequential Cycloaddition Reactions
Jing Liu1, Yaqun Dong2, Miao Li1
1School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China.
Abstract:
Herein, we report the successful synthesis of a series of asymmetric bistetrazole-based energetic compounds (4, 8, 4a-c, and 5a-c) starting from 2-(5-amino-4-nitro-1H-pyrazol-3-yl)-2H-5-cyanotetrazol (3), which was obtained via the reaction of 3,5-diamino-4-nitropyrazole hydrochloride with diazoacetonitrile using a [3 + 2] cycloaddition strategy. All newly synthesized compounds displayed superior detonation performances, particularly 2'-(5-amino-4-nitro-1H-pyrazol-4-yl)-2H,2'H-5,5'-bistetrazole (4), which exhibited exceptional overall performances. These findings underscore the potential of asymmetric bistetrazole derivatives as promising candidates for the development of advanced energetic materials.
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Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.


