Conclusions
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1.
In the reaction of Mg vapors with 1,1-dibromo-2,2-dimethylcyclopropane at 77°K in a medium of solvating solvents, debromination of the starting gem-magnesium dibromide by a radical mechanism with subsequent cleavage of hydrogen atoms from the solvent by the radicals formed is the basic direction of the reaction.
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2.
The capacity of metal vapors to debrominate gem-dibromocyclopropanes decreased in the order of Mg, Al, Zn.
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3.
In the reaction of Cr, Ti, Fe, and Cu vapors with CH2Cl2 and CH2Br2 at 77°K, cleavage of one halogen atom and recombination of the ·CH2X radicals generated occurred with formation of 1,2-dihalogenated ethanes.
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Literature cited
O. M. Nefedov, A. I. D'yachenko, and A. K. Prokof'ev, Usp. Khim.,46, 1787 (1977).
D. A. Filder, J. R. Jones, S. L. Clark, and H. Stange, J. Am. Chem. Soc.,77, 6634 (1955).
J. Villieras, J. Organomet. Chem.,34, 202 (1972).
V. V. Zagorskii, Dissertation, Moscow (1980).
P. L. Timms and T. W. Turney, Adv. Organomet. Chem.,15, 53 (1977).
W. E. Doering and P. M. La Flamme, Tetrahedron,2, 73 (1958).
V. A. Kargin, V. A. Kabanov, and V. P. Zubov, Vysokomol. Soedin.,2, 303 (1960).
D. Gruen, in: Cryochemistry [Russian translation], Mir, Moscow (1979), p. 552.
V. N. Kondrat'ev, Energies of Chemical Bond Cleavage. Ionization Potentials and Electron Affinities [in Russian], Nauka, Moscow (1974).
S. A. Smirnov, I. A. Oreshkin, V. G. Zaikin, and B. A. Dolgoplosk, Dokl. Akad. Nauk SSSR,245, 1400 (1979).
S. P. Kolesnikov, S. L. Povarov, A. Ya. Shteinshneider, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., 415 (1982).
O. A. Nesmeyanova, T. Y. Rudashevskaya, A. I. Dyachenko, S. F. Savilova, and O. M. Nefedov, Synthesis,4, 296 (1982).
A. I. D'yachenko, O. S. Korneva, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., 2432 (1980).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 861–864, April, 1984.
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Kolesnikov, S.P., Povarov, S.L., Tsvetkov, S.Y. et al. Reaction of metal vapors with gem-dihalides of the methane and cyclopropane series. Russ Chem Bull 33, 793–796 (1984). https://doi.org/10.1007/BF00947835
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DOI: https://doi.org/10.1007/BF00947835