Skip to main content
Log in

Cycloalkylation of compounds in the series of phosphorus-substituted derivatives of acetic acid

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

1-Phosphoryl-substituted cyclopropanes, cyclobutanes, and cyclopentanes were obtained by the reaction of phosphoryl-substituted esters and nitriles of acetic acid with α,ω-dihaloalkanes. The influence of the CH-acidity of the starting compounds and electrophilicity of the alkylating agent on the reaction rate was examined.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. T. Hirao, M. Hagihara, and T. Agawa, Bull. Chem. Soc. Jpn.,58, No. 11, 3104 (1985).

    Google Scholar 

  2. D. Seyferth and R. S. Harmor, J. Org. Chem.,36, No. 1, 128 (1971).

    Google Scholar 

  3. D. Seyferth, R. S. Harmor, and P. Hilbert, J. Org. Chem.,36, No. 10, 1379 (1971).

    Google Scholar 

  4. R. D. Gordeev and A. M. Pudovik, Zh. Obshch. Khim.,49, No. 4, 728 (1979).

    Google Scholar 

  5. L. Maier, Phosphorus Sulfur,14, No. 3, 295 (1983).

    Google Scholar 

  6. H. Schmidbaur and T. Pollok, Helv. Chim. Acta,67, No. 8, 2175 (1984).

    Google Scholar 

  7. W. H. Perkin, Ber.,1, 1739 (1983).

    Google Scholar 

  8. N. S. Zefirov, T. S. Kuznetsova, S. I. Kozhushkov, et al., Zh. Org. Khim.,19, No. 2, 541 (1983).

    Google Scholar 

  9. M. M. Gantaeva, Candidate of Chemical Sciences Dissertation, Baku (1987).

  10. P. V. Kazakov, L. V. Kovalenko, I. L. Odinets, and T. A. Mastryukova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2150 (1989).

    Google Scholar 

  11. É. S. Petrov, E. N. Tsvetkov, M. I. Terekhova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 534 (1976).

    Google Scholar 

  12. É. S. Petrov, E. N. Tsvetkov, S. P. Mesyats, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 782 (1976).

    Google Scholar 

  13. M. I. Kabachnik and T. A. Mastryukova, Dokl. Akad. Nauk SSSR,260, No. 4, 893 (1981).

    Google Scholar 

  14. A. G. Matveeva, M. I. Terekhova, N. P. Nesterova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2067 (1988).

    Google Scholar 

  15. M. Fedozynskii, K. Wojciechowski, Z. Matacz, and M. Makosza, J. Org. Chem.,43, No. 24, 4682 (1978).

    Google Scholar 

  16. A. Gordon and R. Ford, A Chemist's Companion: A Handbook of Practical Data, Techniques, and Reference, Wiley-Interscience, New York (1973).

    Google Scholar 

  17. D. J. Martin and C. E. Ciziffin, J. Org. Chem.,30, No. 12, 4034 (1965).

    Google Scholar 

  18. A. N. Pudovik and N. M. Lebedeva, Zh. Obshch. Khim.,25, No. 12, 2235 (1955).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1873–1880, August, 1990.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kazakov, P.V., Odinets, I.L., Laretina, A.P. et al. Cycloalkylation of compounds in the series of phosphorus-substituted derivatives of acetic acid. Russ Chem Bull 39, 1702–1708 (1990). https://doi.org/10.1007/BF00961505

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00961505

Keywords

Navigation