A straightforward preparation of benzo[f]naphtho[b][1,4]oxazepines from TNT |
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| Authors: | Alexander V Samet Konstantine A Kislyi Victor N Marshalkin Yuri A Strelenko Mikhail M Raihstat Yulia V Nelyubina Victor V Semenov |
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| Institution: | a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., 119991 Moscow, Russian Federation
b A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation |
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| Abstract: | 2,4,6-Trinitrotoluene readily reacts with 1-nitroso-2-naphthol to afford 9,11-dinitrobenzof]naphtho2,1-b]1,4]oxazepine. The nitro groups of the latter undergo displacement by O- and S-nucleophiles with preferential substitution of the 11-NO2 (peri-nitro group). The structures of the substitution products are confirmed by X-ray diffraction and 1H NMR NOE experiments. |
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| Keywords: | 2 4 6-Trinitrotoluene 1-Nitroso-2-naphthol Benzo[f]naphtho[b][1 4]oxazepines SNAr reactions |
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