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

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 -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.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1624–1630, July, 1989.