Abstract
New process direction was found in the reaction of polyfluoroarenethiols with fluorodichloromethane, chloroform, and bromoform in an alkaline medium consisting in the replacement of the thiol group by a hydrogen atom. This process competes with the formation of expected products, dihalomethyl polyfluoro-aryl sulfides and tris(arylsulfanyl)methanes. In reaction of 2,3,5,6-tetrafluorobenzenethiol with dichloro-methane bis(2,3,5,6-tetrafluorophenylsulfanyl)methane was obtained. Reactions of polyfluoroarenethiols with pentafluorobenzyl chloride occur mainly with the substitution of the chlorine atom, with pentafluorobenzal chloride and with pentafluorobenzotrichloride a substitution of a fluorine atom in the para-position takes place.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Molecular Medicine and Medicinal Chemistry. vol. 6. Fluorine in Pharmaceutical and Medicinal Chemistry. From Biophysical Aspects to Clinical Applications, Gouverneur, V. and Miller, K., Eds., Imperial College Press, 2012.
Zou, Y., Spokoyny, A.M., Zhang, C., Simon, M.D., Yu, H., Lin, Y.-S., and Pentelute, B.L., Org. Biomol. Chem., 2014, vol. 12, p. 566.
Spokoyny, A.M., Zou, Y., Ling, J.J., Yu, H., Lin, Y.-S., and Pentelute, B.L., J. Am. Chem. Soc., 2013, vol. 135, p. 5946.
Maksimov, A.M., Kireenkov, V.V., and Platonov, V.E., Russ. Chem. Bull., 1996, vol. 45, p. 153.
Khalfina, I.A., Beregovaya, I.V., and Vlasov, V.M., Russ. J. Org. Chem., 2003, vol. 39, p. 1104.
Goralski, C.T. and Burk, G.A., J. Org. Chem., 1977, vol. 42, p. 3094.
Wragg, R.T., Tetrahedron Lett., 1971, vol. 12 p. 2475.
Kirmse, W., Carbene Chemistry, New York and London: Academic Press, 1964.
Uno, H., Sakamoto, K., Semba, F., and Suzuki, H., Bull. Chem. Soc. Jpn., 1992, vol. 65, p. 210.
Nefedov, O.M., Ioffe, A.I., and Manchikov, L.G., Khimiya karbenov (Chemistry of Carbenes), Moscow: Khimiya, 1990.
Pokonova, Yu.V., Galoidsulfidy. Sposoby polucheniya, svoistva, primenenie galoidtioefirov (Haloidsulfides. Methods for the Preparation, Properties, Application of halothioethers), Leningrad: Izd. Leningradskogo Univer., 1977.
Ayres, D.C., Carbaniones in Synthesis, London: Oldbourne Press, 1966.
Gierczyk, B., Wojciechowski, G., Brzezinski, B., Grech, E., and Schroeder, G., J. Phys. Org. Chem., 2001, vol. 14, p. 691.
Vlasov, V.M., Reaktsionnaya sposobnost’ poliftoraromaticheskikh soedinenii (Reactivity of Polyfluoroaromatic Compounds), Novosibirsk: Nauka, 1983.
Fizer, L.F. and Fizer, M., Reagents for Organic Synthesis, New York, London, Sydney: John Wiley & Sons, 1968.
Awaleh, M.O., Badia, A., and Brisse, F., Cryst. Growth Des., 2005, vol. 5, p. 1897.
Berthou, J., Jeminet, G., Laurent, A., Rerat, B., and Rerat, C., C. R. Acad. Sci., Ser. C (Chim)., 1970, vol. 271, p. 516.
Maruta, T., Sugihara, Y., Tanaka, S., Ishii, A., and Nakayama, J., Bull. Chem. Soc. Jpn., 1998, vol. 71, p. 1187.
Maksimov, A.M. and Platonov, V.E., Fluorine Notes, 1999, vol. 4. www.fluorine.ruNotes→chive.html.
Coe, P.L., Stuart, A.M., and Moody, D.J., J. Chem. Soc., Perkin Trans. 1, 1998, p. 1807.
Pushkina, L.N., Stepanov, A.P., Zhukov, V.S., and Naumov, A.D., Zh. Org. Chem., 1972, vol. 8, p. 586.
Dickson, R.S. and Sutcliffe, G.D., Austral. J. Chem., 1973, vol. 26, p. 63.
Krasnov, V.I. and Platonov, V.E., Russ. J. Org. Chem., 2000, vol. 36, p. 1488.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © R.A. Bredikhin, A.M. Maksimov, Yu.V. Gatilov, V.V. Kireenkov, V.E. Platonov, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 11, pp. 1582–1590.
Rights and permissions
About this article
Cite this article
Bredikhin, R.A., Maksimov, A.M., Gatilov, Y.V. et al. Reactions of polyfluorobenzenethiols with polyhalomethanes and their derivatives in an alkaline medium. Russ J Org Chem 51, 1551–1559 (2015). https://doi.org/10.1134/S1070428015110068
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428015110068