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Electrochemical reduction of 1,1-dihalo-2,2-disubstituted cyclopropanes

  • Physical Chemistry
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Bulletin of the Russian Academy of Sciences, Division of chemical science Aims and scope

Abstract

The electrochemical reduction of 1,1-dihalo-2-R-2-methylcyclopropanes was studied by polarography and preparative electrolysis. A mixture of stereoisomeric monoboro- and monochlorocyclopropanes was obtained with preparative yield of 60–70% in preparative electroreduction in methanol against a background of 0.1 M LiClO4. In the case of bromine derivatives of cyclopropanes (except when R = CN) an effect was found on the part of the current density on the ratio of cis and trans isomers, which was interpreted as a change, in dependence on current density, of the contributions of the reactions of reduction of the starting compounds (SN2 mechanism) and ionic pairs (SN1 mechanism). The effect of the solvent (CHCl3, DMF, DMSO, MeOH) and background salt (LiClO4, Et4NBr) on the ratio of stereoisomers is in agreement with this interpretation.

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References

  1. J. Y. Becker,Electrochemistry of the Cyclopropyl Group. The Chemistry of the Cyclopropyl Group, Z. Rappoport (ed.) (1987).

  2. S. Patai,The Chemistry of the Carbon-Halogen Bond, Vol. 2 (1973), p. 982.

    Google Scholar 

  3. A. I. D'yachenko, S. F. Savilova, N. A. Abramova, T. Yu. Rudashevskaya, O. A. Nesmeyanova, and O. M. Nefedov,Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1688 (1980).

  4. E. V. Dehmlow, M. Lissel, and J. Heider,Tetrahedron Lett., 33, No. 3, 363.

  5. M. M. Latypova, L. V. Katerinich, L. I. Baranova, V. V. Plemenkov, and I. G. Bolesov,Zh. Org. Khim. 18, No. 12, 2552 (1982).

    Google Scholar 

  6. Yu. M. Kargin, V. Z. Kondranina, and M. I. Semakhina,Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 278 (1971).

  7. H. Ymanaka, R. Oshima, K. Teramura, and T. Ando,J. Org. Chem. 37, No. 11, 1734 (1972).

    Google Scholar 

  8. M. Bakhbukh, Yu. K. Grishin, N. I. Yakushkina, A. A. Formanovskii, and I. G. Bolesov,Dokl. Akad. Nauk SSSR 248, No. 3, 622 (1979).

    Google Scholar 

  9. M. M. Baizer,Organic Electrochemistry, Dekker, New York (1973).

    Google Scholar 

  10. A. I. Fry and R. H. Moore,J. Org. Chem. 33, 1283 (1968).

    Google Scholar 

  11. R. Harard, S. Jaonnet, and A. Tallec,Electrochim. Acta 28, No. 8, 1095 (1983).

    Google Scholar 

  12. Summaries of Reports of All-Union Conference on Mechanisms of Reactions of Nucleophilic Substitution and Addition, Donetsk (1981).

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Authors
  1. Yu. M. Kargin
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  2. E. I. Gritsenko
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  3. V. V. Yanilkin
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  4. V. V. Plemenkov
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  5. L. K. Dubovik
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  6. N. I. Maksimyuk
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  7. B. M. Garifullin
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  8. Sh. K. Letypov
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  9. A. V. Il'yasov
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Additional information

A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Science Center, Russian Academy of Sciences, Kazan. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 9, pp. 2023–2032, September, 1992.

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Kargin, Y.M., Gritsenko, E.I., Yanilkin, V.V. et al. Electrochemical reduction of 1,1-dihalo-2,2-disubstituted cyclopropanes. Russ Chem Bull 41, 1572–1579 (1992). https://doi.org/10.1007/BF00863575

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  • DOI: https://doi.org/10.1007/BF00863575

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