Abstract:
N-Fluorination of Na-salts of polynitrated bipyrazoles and pyrazole-based fused heterocycles with fluorine–nitrogen mixture (10% F2) at −60 to −70°C in MeOH in the presence of NaF occurs regiospecifically at the nitrogen atom most distant from nitro groups.
Document Type:
Article
Language: English
Citation:
I. L. Dalinger, T. K. Shkineva, I. A. Vatsadze, G. P. Popova, S. A. Shevelev, “N-Fluoro derivatives of nitrated pyrazole-containing fused heterocycles”, Mendeleev Commun., 21:1 (2011), 48–49
Linking options:
https://www.mathnet.ru/eng/mendc2863
https://www.mathnet.ru/eng/mendc/v21/i1/p48
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S. G. Zlotin, I. L. Dalinger, N. N. Makhova, V. A. Tartakovsky, “Nitro compounds as the core structures of promising energetic materials and versatile reagents for organic synthesis”, Russian Chem. Reviews, 89:1 (2020), 1–54
Nadezhda V. Palysaeva, Aleksei G. Gladyshkin, Irina A. Vatsadze, Kyrill Yu. Suponitsky, Dmitry E. Dmitriev, Aleksei B. Sheremetev, “N-(2-Fluoro-2,2-dinitroethyl)azoles: a novel assembly of diverse explosophoric building blocks for energetic compound design”, Org. Chem. Front., 6:2 (2019), 249
Igor L. Dalinger, Kyrill Yu. Suponitsky, Tatyana K. Shkineva, David B. Lempert, Aleksei B. Sheremetev, “Bipyrazole bearing ten nitro groups – a novel highly dense oxidizer for forward-looking rocket propulsions”, J. Mater. Chem. A, 6:30 (2018), 14780
V Reddy, Energetic Materials, 2017, 3
Xiao-Qin Feng, Duan-Lin Cao, Jian-Lan Cui, “Synthesis and Thermal Decomposition Mechanism of the Energetic Compound 3,5-Dinitro-4-nitroxypyrazole”, Journal of Energetic Materials, 34:3 (2016), 288
T. S. Kon'kova, E. A. Miroshnichenko, A. B. Vorob'ev, Yu. N. Matyushin, T. K. Shkineva, I. L. Dalinger, “Enthalpies of formation of nitrodiazoles”, Russ Chem Bull, 65:11 (2016), 2612
Galina N. Lipunova, Emiliya V. Nosova, Valery N. Charushin, Oleg N. Chupakhin, “Fluorine-containing pyrazoles and their condensed derivatives: Synthesis and biological activity”, Journal of Fluorine Chemistry, 175 (2015), 84
V. V. Dubikhin, G. M. Nazin, V. G. Prokudin, Z. G. Aliev, I. A. Vatsadze, S. A. Shevelev, I. L. Dalinger, “Kinetics and mechanism of thermal decomposition of nitropyrazoles”, Russ Chem Bull, 64:1 (2015), 127
Igor L. Dalinger, Irina A. Vatsadze, Tatyana K. Shkineva, Alexandr V. Kormanov, Andrei M. Kozeev, Boris B. Averkiev, Alexandr I. Dalinger, Mikhail K. Beklemishev, Aleksei B. Sheremetev, “Synthesis and investigation of isomeric mono- and dinitro derivatives of 3-methyl-4-(pyrazol-3-yl)furazan”, Chem Heterocycl Comp, 51:6 (2015), 545
I. L. Dalinger, A. Kh. Shakhnes, K. A. Monogarov, K. Yu. Suponitsky, A. B. Sheremetev, “Novel highly energetic pyrazoles: N-fluorodinitromethyl and N-[(difluoroamino)dinitromethyl] derivatives”, Mendeleev Commun., 25:6 (2015), 429–431
Santos Fustero, Antonio Simón-Fuentes, Oscar Delgado, Raquel Román, Fluorine in Heterocyclic Chemistry Volume 1, 2014, 279
Andrei A. Gakh, Topics in Heterocyclic Chemistry, 27, Halogenated Heterocycles, 2011, 33
Igor L. Dalinger, Tatyana K. Shkineva, Irina A. Vatsadze, Galina P. Popova, Svyatoslav A. Shevelev, “ChemInform Abstract: N‐Fluoro Derivatives of Nitrated Pyrazole‐Containing Fused Heterocycles.”, ChemInform, 42:26 (2011)
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