Репост из: Organic Letters ASAP
Modular Synthesis of Dinitramino-Functionalized Pyrazole-Tetrazole and Its Derivatives: Achieving Superior Detonation Performance
Lingzhun Meng, Lei Liu, Zijian Li, Yuji Liu, Wei Huang*, Yongxing Tang
Abstract: A modular synthetic strategy for the construction of 3,5-dinitramino-4-(1H-tetrazol-5-yl)-1H-pyrazole (3) and its salts (3a–3d) was reported. The route hinges on a [3 + 2] cycloaddition to forge the pyrazole-tetrazole backbone, overcoming the steric constraints of multisubstituted pyrazoles, followed by regioselective nitration and salt formation with nitrogen-rich bases. Comprehensive characterization and performance evaluation revealed that the synergistic effect of the nitramino and tetrazole moieties significantly enhanced molecular packing density and detonation performance. Notably, the hydroxylammonium salt 3a features an exceptional detonation velocity of 9335 m·s–1 and a detonation pressure of 39.1 GPa and the hydrazinium salt 3b reaches a detonation velocity of 9350 m·s–1 and a detonation pressure of 36.1 GPa, while maintaining acceptable mechanical sensitivities. This work establishes a versatile platform for the design of high-energy-density materials by integrating bridged-ring heterocycles with dual functionalization, offering a promising direction for next-generation energetic materials.
❯ Link to the article
Lingzhun Meng, Lei Liu, Zijian Li, Yuji Liu, Wei Huang*, Yongxing Tang
Abstract: A modular synthetic strategy for the construction of 3,5-dinitramino-4-(1H-tetrazol-5-yl)-1H-pyrazole (3) and its salts (3a–3d) was reported. The route hinges on a [3 + 2] cycloaddition to forge the pyrazole-tetrazole backbone, overcoming the steric constraints of multisubstituted pyrazoles, followed by regioselective nitration and salt formation with nitrogen-rich bases. Comprehensive characterization and performance evaluation revealed that the synergistic effect of the nitramino and tetrazole moieties significantly enhanced molecular packing density and detonation performance. Notably, the hydroxylammonium salt 3a features an exceptional detonation velocity of 9335 m·s–1 and a detonation pressure of 39.1 GPa and the hydrazinium salt 3b reaches a detonation velocity of 9350 m·s–1 and a detonation pressure of 36.1 GPa, while maintaining acceptable mechanical sensitivities. This work establishes a versatile platform for the design of high-energy-density materials by integrating bridged-ring heterocycles with dual functionalization, offering a promising direction for next-generation energetic materials.
❯ Link to the article