Conclusions
-
1.
Oxidation of 5-R1-2R2-4H-imidazole 1,3-dioxides in methanol with lead dioxide leads to the formation of stable nitroxyl and nitronylnitroxyl radicals with methoxy groups at the α-carbon atom of the radical center. The ratio between these radicals is determined by the electronic character of the substituents at the 2- and 5-positions of the heterocyclic ring.
-
2.
Oxidation of 4H-imidazole 1-oxides and 4H-imidazole 3-oxides in methanol with lead dioxide leads to the formation of iminonitroxyl radicals.
-
3.
Oxidation of 2-unsubstituted 4H-imidazole 1,3-dioxides and 4H-imidazole 3-oxides in alcohols by lead or manganese dioxides leads to 2,2-dialkoxy-substituted stable nitroxyl radicals, which are derivatives of 3-imidazoline 3-oxide and 3-imidazoline.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
I. A. Grigor'ev, L. B. Volodarsky, V. F. Starichenko, et al., Tetrahedron Lett.,26, No. 41, 5085 (1985).
I. A. Kirilyuk, I. A. Grigor'ev, and L. B. Volodarskii, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, No. 9(2), 99 (1989).
I. A. Grigor'ev, I. A. Kirilyuk, and L. B. Volodarskii, Khim. Geterotsikl. Soedin., No. 12, 1640 (1988).
Atlas of Spectra of Aromatic and Heterocyclic Compounds [in Russian], V. A. Koptyug (ed.), Novosibirsk Inst. Org. Khim. Sib. Otd. Akad. Nauk SSSR, No. 40, Novosibirsk (1989).
Atlas of Carbon Magnetic Resonance Spectra [in Russian], V. A. Koptyug and M. I. Podgornaya (eds.), Novosibirsk Inst. Org. Khim. Sib. Otd. Akad. Nauk SSSR, No. 4, Novosibirsk (1985).
E. F. Ullman, J. H. Osiecky, D. J. B. Boocock, and R. Darcy, J. Am. Chem. Soc.,94, 7049 (1972).
E. F. Ullman, L. Call, and J. H. Osiecky, J. Org. Chem.,35, 3623 (1970).
V. V. Khramtsov, L. M. Weiner, A. Z. Gogolev, et al., Magn. Res. Chem.,24, 199 (1986).
I. K. Korobeinicheva, M. M. Mitasov, V. S. Kobrin, and L. B. Volodarskii, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, No. 2(1), 96 (1976).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1624–1630, July, 1989.
Rights and permissions
About this article
Cite this article
Grigor'ev, I.A., Kirilyuk, I.A., Starichenko, V.F. et al. Oxidative alkoxylation of 4H-imidazole N-oxides as a new method of synthesis of stable nitroxyl radicals of the 2- and 3-imidazoline series with alkoxy groups at the α-carbon atom of the radical center. Russ Chem Bull 38, 1488–1494 (1989). https://doi.org/10.1007/BF00978444
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00978444