Abstract
2,3-Dihydro-3-O-(1,4-naphthoquinon-2-yl)-2-oxo-1,4-naphthoquinones are the products of oxidative coupling of substituted 2-hydroxy-1,4-naphthoquinones (regardless of the presence of peri-hydroxy groups in their structures) under the action of lead dioxide.
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L. S. Stepanenko, O. E. Krivoshchekova, P. S. Dmitrenok, and O. B. Maximov, Phytochemistry, 1997, 46, 565.
A. Ya. Chizhova, T. Yu. Kochergina, V. Ph. Anufriev, V. A. Denisenko, and V. P. Glazunov, Izv. Akad. Nauk, Ser. Khim., 1999, 947 [Russ. Chem. Bull., 1999, 48, 938 (Engl. Transl.)].
S. C. Hooker, J. Am. Chem. Soc., 1936, 58, 1168.
M. J. Ettlinger, J. Am. Chem. Soc., 1950, 72, 3472.
L. J. Bellamy, The Infra-red Spectra of Complex Molecules, Chapman and Hall, London, 1975, 133.
A. Ya. Tchizhova, V. Ph. Anufriev, V. P. Glazunov, and V. A. Denisenko, Izv. Akad. Nauk, Ser. Khim., 2000, 465 [Russ. Chem. Bull., Int. Ed., 2000, 49, 466].
A. Ya. Tchizhova, V. Ph. Anufriev, V. P. Glazunov, V. A. Denisenko, and O. P. Moiseenko, Synth. Commun., 1999, 29, 3971.
A. Ya. Tchizhova, Ph. D. (Chem.) Thesis, Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, Vladivostok, 1996, 155 pp. (in Russian).
G. V. Malinovskaya, A. Ya. Chizhova, and V. Ph. Anufriev, Izv. Akad. Nauk, Ser. Khim., 1999, 1019 [Russ. Chem. Bull., 1999, 48, 1010 (Engl. Transl.)].
N. Donaldson, The Chemistry and Technology of Naphthalene Compounds, Arnold, London, 1960.
H. Singh, T. L. Folk, and P. J. Scheuer, Tetrahedron, 1969, 25, 5301.
J. P. Perdew, K. Burke, and M. Ernzerhof, Phys. Rev. Lett., 1996, 787, 3865.
D. N. Laikov, Chem. Phys. Lett., 1997, 281, 151.
M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyene, S. J. Su, T. L. Widus, M. Dupuis, and J. A. Montgomery, J. Comput. Chem., 1993, 14, 1347.
P. J. Stevens, F. J. Devlin, C. F. Chablowski, and M. J. Frish, J. Phys. Chem., 1994, 98, 11623.
C. F. Koelsch and D. J. Byers, J. Am. Chem. Soc., 1940, 62, 560.
L. F. Fieser and M. Fieser, Reagents for Organic Synthesis, J. Wiley and Sons, New York— London—Sydney, 1968.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 294—298, February, 2006.
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Yakubovskaya, A.Y., Kochergina, T.Y., Denisenko, V.A. et al. Synthesis and structure elucidation of oxidative coupling products of 2-hydroxy-1,4-naphthoquinones. Russ Chem Bull 55, 301–305 (2006). https://doi.org/10.1007/s11172-006-0252-9
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DOI: https://doi.org/10.1007/s11172-006-0252-9