Chemistry of Heterocyclic Compounds

, Volume 16, Issue 2, pp 179–182 | Cite as

Sigma complexes in the pyrimidine series. 2. σ Complexes of 5-nitropyrimidine and methoxy-substituted 5-nitropyrimidines with the acetone anion

  • V. M. Cherkasov
  • G. Ya. Remennikov
  • A. A. Kisilenko
  • E. A. Romanenko


The corresponding σ complexes of the Meisenheimer type, viz., anions of the potassium salts of 6H-5-nitro-6-acetonylpyrimidines, were obtained and isolated in the reaction of 5-nitro-, 5-nitro-4-methoxy-, 5-nitro-2-methoxy-, and 5-nitro-2,4-dimethoxypyrimidines with acetone in the presence of potassium hydroxide. The structures of the complexes were proved by means of the PMR, IR, and UV spectra. It is shown that the acetone anion in all cases adds to the methoxy-unsubstituted position of the pyrimidine ring, whereas nucleophilic attack takes place at the C4 atom when the 2 and 4 positions are free.


Potassium Acetone Hydroxide Organic Chemistry Pyrimidine 
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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    V. M. Cherkasov, G. Ya. Remennikov, and E. A. Romanenko, Khim. Geterotsikl. Soedin., No. 10, 1389 (1978).Google Scholar
  2. 2.
    M. Kimura, N. Obi, and M. Kawazai, Chem. Pharm. Bull.,17, 299 (1969).Google Scholar
  3. 3.
    L. Bellamy, Infrared Spectra of Complex Molecules, Methuen, London (1958).Google Scholar
  4. 4.
    A. V. Iogansen and G. D. Litovchenko, Zh. Prikl. Spektrosk.,3, 539 (1965).Google Scholar
  5. 5.
    M. Strauss, Chem. Rev.,70, 667 (1970).CrossRefGoogle Scholar
  6. 6.
    É. G. Kaminskaya, S. S. Gitis, and A. Ya. Kaminskii, Zh. Prikl. Spektrosk.,23, 243 (1975).Google Scholar
  7. 7.
    H. C. van der Plas, H. Jogejan, and A. Koudijs, J. Heterocycl. Chem.,15, 485 (1978).CrossRefGoogle Scholar
  8. 8.
    D. J. Brown and R. V. Foster, Austr. J. Chem.,19, 2321 (1966).CrossRefGoogle Scholar
  9. 9.
    D. M. Besly and A. A. Goldberg, J. Chem. Soc., 4997 (1957).Google Scholar
  10. 10.
    M. E. C. Biffin, D. J. Brown, and T. C. Lee, Austr. J. Chem.,20, 1041 (1967).Google Scholar

Copyright information

© Plenum Publishing Corporation 1980

Authors and Affiliations

  • V. M. Cherkasov
    • 1
  • G. Ya. Remennikov
    • 1
  • A. A. Kisilenko
    • 1
  • E. A. Romanenko
    • 1
  1. 1.Institute of Organic ChemistryAcademy of Sciences of the Ukrainian SSRKiev

Personalised recommendations