Conclusions
Upon reaction of perfluoro-3-methylindene and perfluoro-1-methyleneindane with hexafluoropropylene oxide at 225°C the corresponding cyclopropane derivatives are formed: perfluoro-la-methyl-1,1a,6,6a-tetrahydrocycloprop[a]indene and perfluorospiro[indane-1,1′-cyclopropane], which are transformed during thermolysis in the presence of bromine into 1-bromo-2-difluorobromomethylperfluoro-1-methylindane and 1-bromo-1-(2-bromotetrafluoroethyl)perfluoroindane respectively, and in the absence of bromine into the starting olefins.
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Literature cited
V. M. Karpov, T. V. Mezhenkova, V. E. Platonov, and G. G. Yakobson, Izv. Akad. Nauk SSSR, Ser. Khim., 2068 (1986).
V. M. Karpov, V. E. Platonov, and G. G. Yakobson, Izv. Akad. Nauk SSSR, Ser. Khim., 2295 (1976).
V. M. Karpov, V. E. Platonov, T. A. Stolyarova, and G. G. Yakobson, Izv. Akad. Nauk SSSR, Ser. Khim., 1586 (1981).
W. E. Parham, H. E. Reiff, and P. Swartzentruber, J. Am. Chem. Soc.,78, 1437 (1956); O. M. Nefedov and A. A. Ivashenko, Izv. Akad. Nauk SSSR, Ser. Khim., 446 (1968); F. Nerdel, G. Blume, and P. Weyerstahl, Tetrahedron Lett., 3867 (1969).
P. Tarrant and E. Stamp, Zh. Vses. Khim. Ova,15, 34 (1970).
A. Greenberg, J. F. Liebman, W. R. Dolbier, et al., Tetrahedron,39, 1533 (1983).
R. A. Mitsch and E. W. Neuvar, J. Phys. Chem.,70, 546 (1966).
J. C. Ferrero and E. H. Staricco, Int. J. Chem. Kinet.,11, 1287 (1979).
V. M. Karpov, V. E. Platonov, I. P. Chuikov, and G. G. Yakobson, Zh. Org. Khim.,19, 2164 (1983).
J. M. Birchall, R. N. Haszeldine, and D. W. Roberts, J. Chem. Soc. Perkin Trans., No. 1, 1071 (1973).
V. M. Karpov, T. V. Mezhenkova, V. E. Platonov, and G. G. Yakobson, J. Fluor. Chem.,28, 121 (1985).
H. E. O'Neal and S. W. Benson, J. Phys. Chem.,72, 1866 (1968).
W. R. Dolbier, Jr., S. F. Sellers, and B. E. Smart, Tetrahedron, Lett.,22, 2953 (1981).
V. M. Karpov, V. E. Platonov, and G. G. Yakobson, Izv. Akad. Nauk SSSR, Ser. Khim., 981 (1975); P. B. Sargeant, J. Org. Chem.,35, 678 (1970); P. B. Sargeant, J. Am. Chem. Soc.,91, 3061 (1969).
T. W. Bastock, A. E. Pedler, and J. C. Tatlow, J. Fluor. Chem.,8, 11 (1976).
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Deceased.
For previous report, see [1].
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1839–1845, August, 1988.
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Chuikov, I.P., Karpov, V.M., Platonov, V.E. et al. Fluoroindenes. 10. Cyclization of difluorocarbene to perfluoro-3-methylindene and perfluoro-1-methyleneindane. Thermolysis and bromination of the resultant cyclopropane derivatives. Russ Chem Bull 37, 1645–1650 (1988). https://doi.org/10.1007/BF00961115
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DOI: https://doi.org/10.1007/BF00961115