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NMR SPECTRA OF CYCLIC NITRONES. 4. SYNTHESIS AND 13C NMR SPECTRA OF 4H-IMIDAZOLE N-OXIDES AND N,N-DIOXIDES
Grigor'ev, I. A.,Kirilyuk, I. A.,Volodarskii, L. B.
, p. 1355 - 1362 (2007/10/02)
4H-Imidazole 1,3-dioxides and 4H-imidazole 3-oxides were obtained by oxidation of 1-hydroxy-3-imidazoline 3-oxides and 1-hydroxy-3-imidazolines with lead and manganese dioxides or the stable nitroxyl radical, while 4H-imidazole 1-oxides were obtained by thermal decomposition of 1-acetoxy-3-imidazoline 3-oxides.Facile oxidation of the ethyl group in 5-ethyl-4H-imidazole 1,3-dioxide and the formation of 5-acetyl-4H-imidazole 3-oxide were observed.It is shown that a strictly determined region of chemical shifts of the C(2), C(5), and C(4) atoms is characteristic for each group of 4H-imidazole N-oxides in the 13C NMR spectra; this makes it possible to clearly establish the position of the N-oxide oxygen atom.
