Advertisement

Chemistry of Heterocyclic Compounds

, Volume 4, Issue 4, pp 481–484 | Cite as

Synthesis of stereoisomeric 1,3-dimethyl- and 1,2,5-trimethyl-4-acyl(benzoyl)-4-piperidinols

  • B. V. Unkovskii
  • N. P. Shulaev
  • Yu. F. Malina
  • O. D. Saralidze
Article
  • 26 Downloads

Abstract

In order to synthesize stereoisometric 4-acyl(benzoyl)-1, 3-dimethyl and-1, 2, 5-trimethyl-4-piperidinols, the reaction of the geometrical isomers of 4-cyano-1, 3-dimethyl- and -1, 2, 5-trimethyl-4-piperidinols and the amines and imidic esters corresponding to them with some alkyl- and arylmagnesium halides, leading to the corresponding isomeric piperidinic α-ketols, has been studied. The dependence of the reactivity of the geometrical isomers of the compounds studied on the spatial orientation of their functional groups has been shown.

Keywords

Ester Organic Chemistry Halide Benzoyl Spatial Orientation 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    B. V. Unkovskii, I. A. Mokhir, and E. M. Urinovich, ZhOKh, 33, 1808, 1963.Google Scholar
  2. 2.
    I. N. Nazarov, B. V. Unkovskii, I. A. Mokhir, and G. S. Gusakova, ZhOKh, 29, 2292, 1959.Google Scholar
  3. 3.
    I. N. Nazarov, A. A. Akhrem, and A. V. Kamernitskii, ZhOKh, 25, 1345, 1955.Google Scholar
  4. 4.
    B. V. Unkovskii, G. S. Gusakova, and I. A. Mokhir, ZhOKh, 30, 3926, 1960.Google Scholar
  5. 5.
    I. N. Nazarov and B. V. Unkovskii, ZhOKh, 26, 3181, 1956.Google Scholar
  6. 6.
    I. N. Nazarov and B. V. Unkovskii, ZhOKh, 26, 3186, 1956.Google Scholar
  7. 7.
    B. S. Rabinovitch and C. A. Winkler, Can. J. Res. 2013, 73, 1942.Google Scholar
  8. 8.
    E. L. Carpenter and H. S. Davis, J. Appl. Chem., 7, 671, 1957.Google Scholar
  9. 9.
    C. A. Weisgerber, U. S. patent no. 2535245, 1952; C. A., 46, 4220, 1952.Google Scholar
  10. 10.
    B. V. Unkovskii, V. B. Belyanin, I. A. Mokhir, and E. M. Urinovich, ZhOKh, 33, 2540, 1963.Google Scholar
  11. 11.
    N. I. Shvetsov, B. V. Unkovskii, I. A. Mokhir, and V. F. Kucherov, Izv. AN SSSR, OKhN, 843, 1961.Google Scholar
  12. 12.
    V. B. Belyanin, B. V. Unkovskii, and I. A. Mokhir, ZhOKh, 33, 2534, 1963.Google Scholar
  13. 13.
    R. I. Ouelette, J. Am. Chem. Soc., 86, 3089, 1964.Google Scholar
  14. 14.
    F. R. Iensen and B. Rickborn, J. Org. Chem., 27, 4606, 1962.Google Scholar
  15. 15.
    P. Reynaud and R. C. Moreau, Bull. Soc. chim. France, 2997, 1965.Google Scholar

Copyright information

© Consultants Bureau 1971

Authors and Affiliations

  • B. V. Unkovskii
    • 1
  • N. P. Shulaev
    • 1
  • Yu. F. Malina
    • 1
  • O. D. Saralidze
    • 1
  1. 1.Lomonosov Moscow Institute of Precision Chemical EngineeringUSSR

Personalised recommendations