Chemistry ofα-hydroxyamino oximes
The reaction of anti-α-hydroxyamino oximes with ketones gives substituted 1-hydroxy-3-imidazoline 3-oxides. The action of hydrogen chloride on the latter and on their acetyl derivatives leads to the isomeric 2-isoimidazole N-oxides differing by the position of the N-oxide oxygen in the isoimidazole ring. The structure of the latter compounds has been established by means of IR, UV, and PMR spectra and has been confirmed by independent synthesis.
KeywordsOxygen Hydrogen Chloride Organic Chemistry Ketone
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- 1.L. B. Volodarskii and A. N. Lysak, KhGS [Chemistry of Heterocyclic Compounds], 904, 1967.Google Scholar
- 2.L. B. Volodarskii, A. N. Lysak, and V. A. Koptyug, KhGS [Chemistry of Heterocyclic Compounds], 766, 1966.Google Scholar
- 3.L. B. Volodarskii, A. N. Lysak, and V. A. Koptyug, Tetrah. let., 1565, 1965.Google Scholar
- 4.I. Thesing and W. Sirrenberg, Chem. Ber.,92, 1748, 1959.Google Scholar
- 5.L. B. Volodarskii and A. N. Lysak, KhGS, collection1, p. 109, 1967.Google Scholar
- 6.F. Asinger, M. Thiel, and R. Sowada, Mon.,90, 402, 1959.Google Scholar
- 7.M. Weiss, J. Am. Chem. Soc.,74, 5193, 1952.Google Scholar
- 8.T. J. Haley, A. M. Fiesher and L. Mavis, Nat.,195, 1012, 1962.Google Scholar
- 9.T. J. Haley, Giorn. Ital. Chemioterap.,6–9, 213, 1962; C. A.,58, 12847a, 1963.Google Scholar
- 10.J. E. Baldwin and N. N. Rogers, Chem. Commun., 524, 1965.Google Scholar
- 11.F. J. Allan and G. G. Allan, Chem. and Ind., 1837, 1964.Google Scholar
- 12.H. Schmidbaur, J. Am. Chem. Soc.,85, 2336, 1963.Google Scholar