Abstract
The nitration, bromination, diazo coupling, sulfonation, and alkylation of the aromatic ring of a series of 2-phosphoryl-substituted phenols have been studied for the first time. 2,6-Diphosphorylphenols have been obtained for the first time via 1,3-phosphorotropic phosphate-phosphonate rearrangement. The alkylation of 2-(diphenylphosphoryl)phenol at the hydroxy group with 2-bromo- and 2-chloroethanols has been studied under conventional heating and microwave irradiation conditions.
Similar content being viewed by others
References
Shuvaev, S., Kotova, O., Utochnikova, V, Vaschenko, A., Puntus, L., Baulin, V., Kuzmina, N., and Tzivadze, A., Inorg. Chem. Commun., 2012, vol. 20, p. 73. doi https://doi.org/10.1016/j.inoche.2012.02.020
Shuvaev, S., Bushmarinov, I.S., Sinev, I., Dmitrienko, A.O., Lyssenko, K.A., Baulin, V, Grünert, W., Tsivadze, A.Yu., and Kuzmina, N.E., Eur. J. Inorg. Chem., 2013, vol. 2013, no. 27, p. 4823. doi https://doi.org/10.1002/ejic.201300540
Ivanova, I.S., Baulin, V.E., Pyatova, E.N., Ilyukhin, A.B., Galkina, E.N., Yakusheva, I.A., Dorovatovskii, P.V., and Tsivadze, A.Yu., Russ. J. Gen. Chem., 2018, vol. 88, no. 9, p. 1524. doi https://doi.org/10.1134/S0044460X18090172
Tsvetkov, E.N., Syundyukova, V.Kh., and Baulin, V.E., Zh. Obshch. Khim., 1987, vol. 57, no. 11, p. 2456.
Kalashnikova, I.P., Baulin, D.V., Baulin, V.E., and Tsivadze, A.Yu., Russ. J. Gen. Chem., 2018, vol. 88, no. 9, p. 1853. doi https://doi.org/10.1134/S1070363218090153
Baulin, V.E., Doctoral (Chem.) Dissertation, Chernogolovka, 2012.
Baulin, V.E., Kalashnikova, I.P., Vikharev, Yu.B., Vikhareva, E.A., Baulin, D.V., and Tsivadze, A.Yu., Russ. J. Gen. Chem., 2018, vol. 88, no. 9, p. 1786. doi https://doi.org/10.1134/S1070363218090049
Rauchfuss, T.B., Inorg. Chem., 1977, vol. 16, no. 11, p. 2966. doi https://doi.org/10.1021/ic50177a062
Melvin, L.S., Tetrahedron Lett., 1981, vol. 22, no. 35, p. 3375. doi https://doi.org/10.1016/S0040-4039(01)81909-2
Dashan, L. and Trippett, S., Tetrahedron Lett., 1983, vol. 24, p. 2033. doi https://doi.org/10.1016/S0040-4039(00)81838-9
Dhawan, B. and Redmore, D., Synth. Commun., 1985, vol. 15, no. 5, p. 411. doi https://doi.org/10.1080/00397918508063819
Onys’ko, P., Suvalova, E., Chudakova, T., and Sinitsa, A., Heteroatom Chem., 1993, vol. 4, no. 4, p. 361. doi https://doi.org/10.1002/hc.520040408
Consiglio, G., Failla, S., Finocchiaro, P., and Siracusa, V., Phosphorus, Sulfur Silicon Relat. Elem., 2002, vol. 177, no. 11, p. 2561. doi https://doi.org/10.1080/10426500214564
Consiglio, G., Failla, S., Finocchiaro, P., and Siracusa, V., Phosphorus, Sulfur Silicon Relat. Elem., 2008, vol. 134, no. 1, p. 413. doi https://doi.org/10.1080/10426509808545482
Minaeva, L., Patrikeeva, L., Kabachnik, M., Beletskaya, I., Orlinson, B., and Novakov, I., Heteroatom Chem., 2011, vol. 22, no. 1, p. 55. doi https://doi.org/10.1002/hc.20656
Häbich, D. and Effenberger, F., Synthesis, 1978, vol. 10, p. 755. doi https://doi.org/10.1055/s-1978-24879
Miller, J., J. Org. Chem., 1987, vol. 52, no. 2, p. 322. doi https://doi.org/10.1021/jo00378a044
Mills, R.J., Horvath, R.F., Sibi, M.P., and Snieckus, V., Tetrahedron Lett., 1985, vol. 26, no. 9, p. 1145. doi https://doi.org/10.1016/S0040-4039(00)98418-1
Evreinov, V.I., Baulin, V.E., Vostroknutova, Z.N., Safronova, Z.V., Krashakova, I.B., Syundyukova, V.Kh., and Tsvetkov, E.N., Bull. Acad. Sci. USSR, Div. Chim. Sci., 1991, vol. 40, no. 9, p. 1759. doi https://doi.org/10.1007/BF00960399
Evreinov, V.I., Baulin, V.E., Vostroknutova, Z.N., Bondarenko, N.A., Syundyukova, V.Kh., and Tsvetkov, E.N., Bull. Acad. Sci. USSR, Div. Chim. Sci., 1989, vol. 38, no. 8, p. 1828. doi https://doi.org/10.1007/BF00957771
Funding
This study was performed under partial financial support by the Russian Foundation for Basic Research (project no. 19-03-00262) in the framework of state assignment for the Institute of Physiologically Active Compounds of the Russian Academy of Sciences.
Author information
Authors and Affiliations
Corresponding author
Additional information
Conflict of Interests
No conflict of interest was declared by the authors.
Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 8, pp. 1206–1215.
Rights and permissions
About this article
Cite this article
Rogacheva, Y.I., Baulin, D.V., Baulin, V.E. et al. Functionalization of 2-Phosphoryl-Substituted Phenols. Russ J Gen Chem 89, 1595–1603 (2019). https://doi.org/10.1134/S1070363219080097
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363219080097