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13C NMR spectroscopy of the ring-chain tautomerism of the product of reduction of dubinidinone

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Abstract

The existence of ring-chain tautomerism between a cyclic semiketal form and an open-chain δ-ketol form of the product of the reduction of dubinidinone has been shown unambiguously by13C NMR spectroscopy, and this has been confirmed by the results of PMR spectroscopy. It has been shown that in the solution in deuteropyridine and deuterodimethyl sulfoxide the tautomeric equilibrium is shifted in the direction of the formation of the cyclic semiketal, while in trifluoroacetic acid it is shifted in the direction of the open-chain δ-ketol. Analysis of the IR spectrum has shown that the product of the reduction of dubinidinone exists predominantly in the cyclic semiketal form in the crystalline state.

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Authors
  1. I. A. Bessonova
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  2. M. R. Yagudaev
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  3. S. Yu. Yunusov
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Additional information

Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 100–104, January–February, 1988.

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Bessonova, I.A., Yagudaev, M.R. & Yunusov, S.Y. 13C NMR spectroscopy of the ring-chain tautomerism of the product of reduction of dubinidinone. Chem Nat Compd 24, 88–91 (1988). https://doi.org/10.1007/BF00597582

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  • DOI: https://doi.org/10.1007/BF00597582

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