Abstract
A reaction of perfluoro-1-methylbenzocyclobutene with pentafluorobenzene in SbF5 medium followed by treating the reaction mixture with water gave rise to perfluoro-1-methyl-1-phenylbenzocyclobutene, perfluoro-1-methyl-2-phenylbenzocyclobutene, 2-hydroxyperfluoro-1-methyl-2-phenylbenzocyclobutene, and also to small amounts of 1-(2-trifluoromethyltetrafluorophenyl)-1-pentafluorophenyl-2,2,2-trifluoroethane, and perfluoro-1-(2-methylphenyl)-1-phenylethylene. In a crystal of (E)-2-hydroxyperfluoro-1-methyl-2-phenylbenzocyclobutene for a dimer molecular pair a π-stacking interaction between pentafluorophenyl groups was found.
Similar content being viewed by others
REFERENCES
Karpov, V.M., Mezhenkova, T.V., Platonov, V.E., Sinyakov, V.R., and Shchegoleva, L.N., Zh. Org. Khim., 2002, vol. 38, p. 1210.
Karpov, V.M., Mezhenkova, T.V., Platonov, V.E., and Sinyakov, V.R., J. Fluorine Chem., 2001, vol. 107, p. 53; Karpov, V.M., Mezhenkova, T.V., Platonov, V.E., and Sinyakov, V.R., J. Fluorine Chem., 2002, vol. 117, p. 73.
Karpov, V.M., Mezhenkova, T.V., Platonov, V.E., and Yakobson, G.G., J. Fluorine Chem., 1985, vol. 28, p. 121; Karpov, V.M., Mezhenkova, T.V., Platonov, V.E., and Yakobson, G.G., Izv., Akad. Nauk SSSR, Ser. Khim., 1985, p. 2315; Karpov, V.M., Mezhenkova, T.V., Platonov, V.E., and Yakobson, G.G., Izv. Akad. Nauk, SSSR, Ser. Khim., 1987, p. 1361.
Karpov, V.M., Mezhenkova, T.V., Platonov, V.E., and Yakobson, G.G., Izv. Akad. Nauk SSSR, Ser. Khim., 1990, p. 1114; Karpov, V.M., Mezhenkova, T.V., and Platonov, V.E., Izv. Akad. Nauk, Ser. Khim., 1992, p. 1419.
Lork, E., Mews, R., Shakirov, M.M., Watson, P.G., and Zibarev, A.V., Eur. J. Inorg. Chem., 2001, p. 2123.
Hunter, C.A., Chem. Soc. Rev., 1994, vol. 23, p. 101; Hunter, C.A., Lawson, K.R., Perkins, J., and Urch, C.J., J. Chem., Soc., Perkin Trans. II, 2001, p. 651.
Filler, R., Mol. Struct. Energ., 1988, vol. 8, p. 19; Williams, J.H., Acc. Chem. Res., 1993, vol. 26, p. 593; Dahl, T., Acta, Chem. Scand., 1994, vol. 48, p. 95; Collings, J.C., Roscoe, K.P., Thomas, R.L., Batsanov, A.S., Stimson, L.M., Howard, J.A.K., and Marder, T.B., New J. Chem., 2001, vol. 25, p. 1410; Vangala, V.R., Nangia, A., and Lynch, V.M., Chem. Commun., 2002, p. 1304.
Tsuzuki, S., Honda, K., Uchimaru, T., Mikami, M., and Tanabe, K., J. Am. Chem. Soc., 2002, vol. 124, p. 104.
Boese, R., Blaeser, D., Latz, R., and Baumen, A., Acta Crystallogr., Sect. C (Cr. Str. Comm.), 1999, vol. C55, IUC 9900036.
Boese, R. and Blaeser, D., Angew. Chem., Int. Ed., 1988, vol. 27, p. 304.
Iida, K., Kawata, E., Komada, K., Saito, M., Kumakura, S., and Yoshioka, M., Acta Crystallogr., Sect. C (Cr. Str., Comm.)., 1998, vol. C54, p. 1938.
Allen, F.H. and Kennard, O., Chemical Design Automation News, 1993, vol. 8, p. 31.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Sinyakov, V.R., Mezhenkova, T.V., Karpov, V.M. et al. Reaction of Perfluoro-1-methylbenzocyclobutene with Pentafluorobenzene in SbF5 Medium. Russian Journal of Organic Chemistry 39, 837–842 (2003). https://doi.org/10.1023/B:RUJO.0000003162.41792.ad
Issue Date:
DOI: https://doi.org/10.1023/B:RUJO.0000003162.41792.ad