Abstract
Tautomeric equilibria ofpara- andana- quinoid forms of 5-hydroxy-1,4-naphthoquinone-4-imines in solutions were studied by UV and1H NMR spectroscopy. Theana-form is electron-withdrawing substituents at position 6.
Similar content being viewed by others
References
K. Hasegawa, M. Sakakibara, T. Ishida, and Y. Ueno,Bull. Chem. Soc. Jpn., 1990,63, 1467.
Off. Ger. 3126108, 1983.
L. V. Ektova, O. P. Petrenko, I. K. Korobeinicheva, and E. P. Fokin, Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 2572 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989,38, 2359 (Engl. transl.)].
S. M. Bloom and G. O. Dudek.Tetrahedron, 1970,26, 1267.
S. M. Bloom and G. O. Dudek,J. Org. Chem., 1971,36, 235.
L. V. Ektova, R. P. Shishkina, and E. P. Fokin,Izv. Akad. Nauk SSSR, Ser. Khim., 1987, 1351 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987,36, 1247 (Engl. Transl.)].
L. V. Ektova, R. P. Shishkina, and E. P. Fokin,Izv. Akad. Nauk SSSR, Ser. Khim., 1988, 1672 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988,37, 1487 (Engl. Transl.)].
L. V. Ektova and A. D. Bukhtoyarova,Sib. Khim. Zh. [Sib. Chem. J.], 1991, No. 3, 84 (in Russian).
L. V. Ektova and A. D. Bukhtoyarova,Sib. Khim. Zh. [Sib. Chem. J.], 1993, No. 2, 105 (in Russian).
K. Klemm, H. Schaefer, and E. Daltrozzo,Chem. Ber., 1979,112, 484.
Jap. Pat. 1165557.
V. V. Lapachev, O. P. Petrenko, and V. P. Mamaev,Usp. Khim., 1990,59, 457 [Russ. Chem. Rev., 1990,59 (Engl. Transl.)].
O. P. Petrenko, V. V. Lapachev, and V. P. Mamaev,Zh. Org. Khim., 1988,24, 1799 [J. Org. Chem. USSR, 1988,24 (Engl. Transl.)].
O. P. Petrenko and V. V. Lapachev,Zh. Org. Khim., 1988,24, 1806 [J. Org. Chem. USSR, 1988,24 (Engl. Transl.)].
M. J. S. Dewar and W. Thiel,J. Am. Chem. Soc., 1977,99, 4899.
L. V. Ektova and R. P. Shishkina,Izv. Ikad. Nauk SSSR, Ser. Khim., 1990, 2851 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990,39, 2588 (Engl. Transl.)].
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 358–362, February, 1997.
Rights and permissions
About this article
Cite this article
Ektova, L.V., Bukhtoyarova, A.D. & Petrenko, O.P. Effect of substitutents on the tautomeric equilibrium of 5-hydroxy-1,4-naphthoquinon-4-imines. Russ Chem Bull 46, 344–349 (1997). https://doi.org/10.1007/BF02494378
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02494378