Russian Journal of General Chemistry

, Volume 89, Issue 1, pp 148–150 | Cite as

Reactions of Lithium Acylates α-Carbanions with 1,2-Diiodoethane

  • A. V. Zorin
  • A. R. ChanyshevaEmail author
  • A. O. Lenkova
  • V. V. Zorin
Letters to the Editor


The interaction of lithium acylates α-carbanions (obtained via metallation of acetic, butyric, and isobutyric acids with lithium diisopropylamide) with 1,2-diiodoethane under argon in tetrahydrofuran at 20–25°C has proceeded as oxidative cross-coupling of enolate anions to form succinic, 2,3-diethylsuccinic, and 2,2,3,3-tetramethylsuccinic acids with yields 50, 53, and 16%, respectively. The products of sequential nucleophilic substitution of iodine atoms with alkyloxycarbonyl species have not been detected.


1,2-diiodoethane dicarboxylic acids lithium acylates α-carbanions metallation oxidative cross-coupling 


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  1. 1.
    Durr, A.M, Jr., Eby, H.H., and Newman, M.S., USA Patent 3210404, 1965, C. A., 1966, vol. 64, p. 1968d.Google Scholar
  2. 2.
    Chanysheva, A.R., Zorin, A.V., and Zorin, V.V., Bash. Khim. Zh., 2015, vol. 22, no. 4, p. 53.Google Scholar
  3. 3.
    Kofron, W.G. and Hauser, C.R., J. Org. Chem., 1970, vol. 35, p. 2085. doi CrossRefGoogle Scholar
  4. 4.
    Bahl, J.J., Bates, R.B., Beavers, W.A., and Mills, N.S., J. Org. Chem., 1976, vol. 41, p. 1620. doi CrossRefGoogle Scholar
  5. 5.
    Zorin, A.V., Zaynashev, A.T., Chanysheva, A.R., and Zorin, V.V., Russ. J. Gen. Chem., 2015, vol. 85, no. 6, p. 914. doi CrossRefGoogle Scholar
  6. 6.
    Chanysheva, A.R., Zorin, A.V., and Zorin, V.V., Bash. Khim. Zh., 2014, vol. 21, no. 2, p. 99.Google Scholar
  7. 7.
    Bilevich, K.А. and Okhlobystin O.Yu., Russ. Chem. Rev., 1968, vol. 37, p. 954. doi CrossRefGoogle Scholar
  8. 8.
    Renaud, P. and Fox, M., J. Org. Chem., 1988, vol. 53, p. 3745. doi CrossRefGoogle Scholar
  9. 9.
    Becker, H.G.O., Berger, W., Domschke, G., Fanghänel, E., Faust, J., Fischer, M., Gentz, F., Gewald, K., Gluch, R., Mayer, R., Müller, K., Pavel, D., Schmidt, H., Schollberg, K., Schwetlick, K., Seiler, E., et al., Organicum: Practical Handbook of Organic Chemistry, Pergamon Press, 1973.Google Scholar
  10. 10.
    Raid, K., Course of Physical Organic Chemistry, Moscow: Mir, 1972.Google Scholar
  11. 11.
    Freidlin, G.N., Aliphatic Dicarboxylic Acids, Moscow: Khimiya, 1978.Google Scholar
  12. 12.
    Eberson, L., Acta Chem. Scand., 1959, vol. 13, p. 40. doi CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • A. V. Zorin
    • 1
  • A. R. Chanysheva
    • 1
    Email author
  • A. O. Lenkova
    • 1
  • V. V. Zorin
    • 1
  1. 1.Ufa State Petroleum Technological UniversityUfaRussia

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