Tautomerism of azine derivatives
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The tautomeric properties of 4-pyrimidinylmethanes were studied in the case of 2-CH3- and 2-CF3-4-pyrimidinylcyanoacetic esters, 2-CH3-4-pyrimidinylnitromethane, and 4-pyrimidinylnitromethane. It was shown by 1H and 13C NMR spectroscopy that an equilibrium with the participation of three tautomeric forms — pyrimidine form A and pyrimidinylidene forms B and C with “o- and p-quinoid” orientations of the double bonds in the heteroring — may be realized in aprotic dipolar solvents (dimethyl sulfoxide).
KeywordsSpectroscopy Ester Organic Chemistry Dimethyl Double Bond
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