Conclusions
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1.
Upon oxidation of 1-hydroxy-4R21-2R2-5,5-dimethyl-3-imidazoline-3-oxides or the corresponding N,N-dioxides of 4H-imidazole with lead dioxide in saturated alcoholic solutions of amines there are formed stable nitronylnitroxyl and nitroxyl radicals of the imidazoline-N-oxide series, which contain a primary or secondary amino group at the α-carbon atom of the radical center.
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2.
The ratio of reaction products depends on the nature of the substituents: donating R1 and accepting R2 favor formation of nitroxyl radicals of 3-imidazoline-3-oxide.
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3.
Upon oxidation of N-oxides of 4H-imidazole in alcoholic solutions of amines iminonitroxyl radicals are formed which contain an amino group at the central carbon atom.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 661–667, March, 1989.
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Grigor'ev, I.A., Starichenko, V.F., Kirilyuk, I.A. et al. Preparation-of stable nitroxyl radicals with an amino group at the α-carbon atom of the radical center by oxidative amination of 4H-imidazole N-oxides. Russ Chem Bull 38, 587–592 (1989). https://doi.org/10.1007/BF00958054
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DOI: https://doi.org/10.1007/BF00958054