Conclusions
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1.
1-Hydroxy- or 1-oxyl-3-imidazoline 3-oxides with acyl, hydroxyalkyl, or oxime groups, or a hydrogen atom, in the 2-position of the heterocycle undergo oxidation in the presence of nucleophiles with the intermediate formation of 4H-imidazole di-N-oxides, to give nitronylnitroxyl radicals.
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2.
A new series of stable nitronylnitroxyl radicals with a functional group in the 4-position have been obtained.
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3.
The electronic effects of the nitronylnitroxyl group have been determined from measurements of the pKa values of the OH and NH2 groups in 4-hydroxy- and 4-amino-5,5-dimethyl-4-phenyl-3-imidazoline 3-oxide 1-oxyl using EPR spectroscopy.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2342–2351, October, 1985.
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Grigor'ev, I.A., Shchukin, G.I., Khramtsov, V.V. et al. Conversion of 3-imidazoline-3-oxide nitroxyl radicals into nitronylnitroxyl radicals. Russ Chem Bull 34, 2169–2177 (1985). https://doi.org/10.1007/BF00963256
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DOI: https://doi.org/10.1007/BF00963256