Conclusions
-
1.
In the presence of an equimolar amount of alkali the aldehyde group of 4-formyl-2, 2,5,5-tetramethyl-3-imidazoline-1-oxyl is oxidized by the nitroxyl radical to the carboxyl group, whereas the alcohol group of 4-hydroxymethyl-2,2,5,5-tetramethyl-3-imidazoline-1-oxyl is oxidized to the carboxyl group in the presence of excess alkali.
-
2.
In a neutral medium the alcohol group of 4-(1-hydroxyethyl)-2,2,5,5-tetramethyl-3-iraidazoline-1 oxyl is oxidized by the nitroxyl radical to the keto group.
Literature cited
H. Schlude, Tetrahedron,29, 4007 (1973).
H. Schlude, Tetrahedron,31, 89 (1975).
I. A. Grigor'ev and L. B. Volodarskii, Zh. Org. Khim.,11, 1328 (1975).
V. A. Golubev, V. D. Sen, and É. G. Rozantsev, Izv. Akad. Nauk SSSR, Ser. Khim.,1974, 2773.
L. B. Volodarskii, G. A. Kutikova, V. S. Kobrin, R. Z. Sagdeev, and Yu. N. Molin, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk,1971, No. 4, Issue 3, 101.
E. G. Rozantsev, Free Iminoxyl Radicals [in Russian], Khimiya (1970), p. 58.
T. K. Sevast'yanova and L. B. Volodarskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1972, 2339.
T. A. Geisman, Organic Reactions [Russian translation], Vol. 2, IL (1950), p. 106.
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 208–210, January, 1978.
Rights and permissions
About this article
Cite this article
Grigor'ev, I.A., Volodarskii, L.B. Participation of nitroxyl radical in oxidation of aldehyde and alcohol groups in 3-imidazoline-1-oxyl. Russ Chem Bull 27, 182–184 (1978). https://doi.org/10.1007/BF01153238
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01153238