Sigma complexes in the pyrimidine series. 2. σ Complexes of 5-nitropyrimidine and methoxy-substituted 5-nitropyrimidines with the acetone anion |
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Authors: | V M Cherkasov G Ya Remennikov A A Kisilenko E A Romanenko |
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Institution: | (1) Institute of Organic Chemistry, Academy of Sciences of the Ukrainian SSR, 252660 Kiev |
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Abstract: | 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.
See 1] for communication 1.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 239–242, February, 1980. |
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