Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Application of adsorption chromatography in work with ferrocene derivatives

  • 144 Accesses

  • 2 Citations

Summary

  1. 1.

    In contact with chromatographic alumina, aralkylferrocenes ΦCH2Ar and α-substituted ferrocenemethanols ΦCH(OH) are oxidized by atmospheric oxygen to the ketones ΦCOR (R=Ar or Alk).

  2. 2.

    On SiO2, in contrast with the behavior found on Al2O3, oxidation occurs extremely readily with formation of those ferrocene derivatives that have electron-donating substituents. Ferrocenemethanols undergo disproportionation and intra- and inter-molecular elimination of water and the formation of ethers. The formation of ethers under these conditions is observed also for polyarylmethanols.

This is a preview of subscription content, log in to check access.

Literature cited

  1. 1.

    P. D. Bartlett, and J. D. McCollum, J. Amer. Chem. Soc.78, 1441 (1956).

  2. 2.

    N. C. Deno, P. T. Groves, J. J. Jaruzelski, and M. N. Lugasch, J. Amer. Chem. Soc.82, 4719 (1960).

  3. 3.

    A. N. Nesmeyanov, É. G. Perevalova and Yu. A. Ustynyuk, Izv. AN SSSR. Otd. khim. n. (1963) (in the press).

  4. 4.

    H. A. Benesi, J. Amer. Chem. Soc.78, 5490 (1956).

  5. 5.

    K. G. Miesserov, Uspekhi khimii22, 284 (1953).

  6. 6.

    M. Rausch, M. Vogel, and H. Rosenberg, J. Organ. Chem.22, 903 (1957).

  7. 7.

    F. S. Arimoto and A. C. Haven, J. Amer. Chem. Soc.77, 6295 (1955).

  8. 8.

    A. N. Nesmeyanov and I. I. Kritskaya, Izv. AN SSSR. Otd. Khim. n. 352 (1962).

  9. 9.

    A. N. Nesmeyanov, É. G. Perevalova, L. S. Shilovtseva and Z. A. Beinoravichute, Dokl. AN SSSR121, 117 (1958).

  10. 10.

    T. V. Antipina and M. D. Sinitsyna, Vestn. MGU, seriya fiz.-mat. i est. nauk, No. 1, 139 (1957).

  11. 11.

    Organic Syntheses [Russian translation], Vol. 1, 82 (1949).

  12. 12.

    A. Zagumenny, Liebigs Ann. Chem.184, 176 (1877).

  13. 13.

    J. W. Brühl, Liebigs Ann. Chem.200, 190 (1880).

Download references

Author information

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Nesmeyanov, A.N., Kritskaya, I.I. & Antipina, T.V. Application of adsorption chromatography in work with ferrocene derivatives. Russ Chem Bull 11, 1685–1690 (1962). https://doi.org/10.1007/BF00920260

Download citation

Keywords

  • Oxidation
  • Oxygen
  • Alumina
  • Ether
  • Chromatography