Abstract:
Depending on the conditions, polyfluorinated alcohols RfCH2OH [Rf = CF3, H(CF2)n; n = 2, 4, 6, 8] replace one or two nitro groups in 1,3,5-trinitrobenzene in the presence of K2CO3 in N-methylpyrrolidone to give the previously unknown 1-polyfluoroalkoxy-3,5-dinitrobenzenes or 1,3-di(polyfluoroalkoxy)-5-nitrobenzenes; the reaction is successful due to the high acidity of RfCH2OH (pKa ≈ 12).
Document Type:
Article
Language: English
Citation:
S. A. Shevelev, M. D. Dutov, M. A. Korolev, O. Yu. Sapozhnikov, A. L. Rusanov, “Replacement of the nitro groups in 1,3,5-trinitrobenzene on treatment with polyfluorinated alcohols”, Mendeleev Commun., 8:2 (1998), 69–70
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https://www.mathnet.ru/eng/mendc4659
https://www.mathnet.ru/eng/mendc/v8/i2/p69
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M. D. Dutov, D. R. Aleksanyan, O. V. Serushkina, E. N. Nesterova, S. A. Shevelev, “Reactions of 1,3,5-trinitrobenzene with primary aliphatic alcohols”, Russ Chem Bull, 67:5 (2018), 822
M. D. Dutov, S. A. Shevelev, V. N. Koshelev, D. R. Aleksanyan, O. V. Serushkina, O. D. Neverova, E. V. Kolvina, E. S. Bobrov, “Dual reactivity of 1-chloro- and 1-bromo-3,5-dinitrobenzenes in aromatic nucleophilic substitution”, Mendeleev Commun., 27:2 (2017), 160–162
S. S. Vorob'ev, M. D. Dutov, I. A. Vatsadze, E. P. Petrosyan, V. V. Kachala, Yu. A. Strelenko, S. A. Shevelev, “Intramolecular cyclization of O-(3,5-dinitrophenyl) and O-(3-amino-5-nitrophenyl) ketoximes, products of transformations of 1,3,5-trinitrobenzene. The synthesis of nitrobenzo[b]furans and 4-hydroxynitroindoles”, Russ Chem Bull, 56:5 (2007), 1020
A. Kh. Shakhnes, S. S. Vorob'ev, S. A. Shevelev, “Selective reduction of one, two, or three nitro groups in 1,3,5-trinitrobenzene with hydrazine hydrate”, Russ Chem Bull, 55:5 (2006), 938
S. S. Vorob'ev, M. D. Dutov, O. V. Serushkina, M. A. Korolev, V. V. Kachala, Yu. A. Strelenko, S. A. Shevelev, “Synthesis of quinolonecarboxylic acids from 1,3,5-trinitrobenzene”, Mendeleev Commun., 16:6 (2006), 318–319
M. D. Dutov, S. S. Vorob'ev, O. V. Serushkina, S. A. Shevelev, B. I. Ugrak, V. V. Kachala, “Reactions of ortho-aminophenols and ortho-aminothiophenols with 1,3,5-trinitrobenzene”, Mendeleev Commun., 16:4 (2006), 230–232
M. D. Dutov, I. A. Vatsadze, S. S. Vorob'ev, S. A. Shevelev, “Synthesis of 4,6-dinitrobenzo[b]furans from 1,3,5-trinitrobenzene”, Mendeleev Commun., 15:5 (2005), 202–204
Vladimir V. Rozhkov, Svyatoslav A. Shevelev, Ivan I. Chervin, Alexander R. Mitchell, Robert D. Schmidt, “Direct Amination of 1-Substituted 3,5-Dinitrobenzenes by 1,1,1-Trimethylhydrazinium Iodide”, J. Org. Chem., 68:6 (2003), 2498
S. A. Shevelev, I. A. Vatsadze, M. D. Dutov, “Substitution for a nitro group in 1,3,5-trinitrobenzene and meta-substituted 1,3-dinitrobenzenes under the action of oximes”, Mendeleev Commun., 12:5 (2002), 196–198
O. Yu. Sapozhnikov, M. D. Dutov, V. V. Kachala, S. A. Shevelev, “Consecutive substitution for three nitro groups in 1,3,5-trinitrobenzene under the action of benzotriazole and other nucleophiles”, Mendeleev Commun., 12:6 (2002), 231–233
O. Yu. Sapozhnikov, M. D. Dutov, M. A. Korolev, V. V. Kachala, S. A. Shevelev, “Substitution for a nitro group in 1,3,5-trinitrobenzene under the action of NH-azoles”, Mendeleev Commun., 11:6 (2001), 232–233
V. V. Rozhkov, S. A. Shevelev, “Synthesis of 5-alkoxy-3-amino-7-nitro-1,2,4-benzotriazine 1-oxides from 1,3,5-trinitrobenzene”, Russ Chem Bull, 49:9 (2000), 1640
M. A. Korolev, M. D. Dutov, S. A. Shevelev, “Replacement of one nitro group in 1,3,5-trinitrobenzene and its analogs under the action of secondary aliphatic amines”, Russ Chem Bull, 48:9 (1999), 1798
A L Rusanov, L G Komarova, M P Prigozhina, S A Shevelev, M D Dutov, M A Korolev, O Yu Sapozhnikov, “New Fluorinated Polyimides Based on 2, 4, 6-Trinitrotoluene Derivatives”, High Performance Polymers, 11:4 (1999), 395
S. A. SHEVELEV, M. D. DUTOV, M. A. KOROLEV, O. YU. SAPOZHNIKOV, A. L. RUSANOV, “ChemInform Abstract: Replacement of the Nitro Groups in 1,3,5‐Trinitrobenzene on Treatment with Polyfluorinated Alcohols.”, ChemInform, 29:39 (1998)
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