Abstract:
A pernitrofuroxan–3,4-dinitrofuroxan–has been synthesized for the first time, and nucleophilic substitution studies show this compound to be a starting material for the synthesis of 4-functionally substituted 3-nitrofuroxans not hitherto readily accessible.
Document Type:
Article
Language: English
Citation:
T. I. Godovikova, O. A. Rakitin, S. P. Golova, S. A. Vozchikova, L. I. Khmel'nitskii, “3,4-Dinitrofuroxan—the First Example of a Pernitro Heterocycle”, Mendeleev Commun., 3:5 (1993), 209–210
Linking options:
https://www.mathnet.ru/eng/mendc5339
https://www.mathnet.ru/eng/mendc/v3/i5/p209
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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
Dmitry M. Bystrov, Leonid L. Fershtat, Nina N. Makhova, “Synthesis and reactivity of aminofuroxans”, Chem Heterocycl Comp, 55:12 (2019), 1143
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Li Xiaohong, Zhang Ruizhou, Zhang Xianzhou, “Computational investigation of the heat of formation, detonation properties of furazan-based energetic materials”, Struct Chem, 24:4 (2013), 1193
N. N. Makhova, A. S. Kulikov, “Advances in the chemistry of monocyclic amino- and nitrofuroxans”, Russian Chem. Reviews, 82:11 (2013), 1007–1033
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