Sigma complexes in the pyrimidine series. 2. σ Complexes of 5-nitropyrimidine and methoxy-substituted 5-nitropyrimidines with the acetone anion
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.
KeywordsPotassium Acetone Hydroxide Organic Chemistry Pyrimidine
Unable to display preview. Download preview PDF.
- 1.V. M. Cherkasov, G. Ya. Remennikov, and E. A. Romanenko, Khim. Geterotsikl. Soedin., No. 10, 1389 (1978).Google Scholar
- 2.M. Kimura, N. Obi, and M. Kawazai, Chem. Pharm. Bull.,17, 299 (1969).Google Scholar
- 3.L. Bellamy, Infrared Spectra of Complex Molecules, Methuen, London (1958).Google Scholar
- 4.A. V. Iogansen and G. D. Litovchenko, Zh. Prikl. Spektrosk.,3, 539 (1965).Google Scholar
- 6.É. G. Kaminskaya, S. S. Gitis, and A. Ya. Kaminskii, Zh. Prikl. Spektrosk.,23, 243 (1975).Google Scholar
- 9.D. M. Besly and A. A. Goldberg, J. Chem. Soc., 4997 (1957).Google Scholar
- 10.M. E. C. Biffin, D. J. Brown, and T. C. Lee, Austr. J. Chem.,20, 1041 (1967).Google Scholar