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E/Z(C=C)-Isomerization of enamines of 3-formyl-4-hydroxycoumarin induced by organic solvents

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Abstract

According to 1? and 13? NMR data, enamines of 3-formyl-4-hydroxycoumarin exist in the keto enamine tautomeric form and undergo Z/E-isomerization around the C=C bond in CDCl3, DMSO-d6, and CD3OD at room temperature. The activation energies of ?/Z-isomerization were measured experimentally and calculated by the B3LYP/6-311++G(d,p) method. An X-ray diffraction study showed that 3-(benzyliminomethyl)chromane-2,4-dione in the crystalline state exists as a mixture of two keto enamine isomers.

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Authors and Affiliations

  1. D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., 125147, Moscow, Russian Federation

    V. F. Traven, I. V. Ivanov, V. S. Lebedev, T. A. Chibisova, B. G. Milevskii & N. P. Solov’eva

  2. Center for Drug Chemistry, 7 Zubovskaya ul., 119815, Moscow, Russian Federation

    V. I. Polshakov

  3. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    G. G. Alexandrov

  4. N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119991, Moscow, Russian Federation

    O. N. Kazheva & O. A. Dyachenko

Authors
  1. V. F. Traven
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  2. I. V. Ivanov
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  3. V. S. Lebedev
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  4. T. A. Chibisova
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  5. B. G. Milevskii
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  6. N. P. Solov’eva
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  7. V. I. Polshakov
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  8. G. G. Alexandrov
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  9. O. N. Kazheva
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  10. O. A. Dyachenko
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Correspondence to V. F. Traven.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1565–1570, August, 2010.

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Traven, V.F., Ivanov, I.V., Lebedev, V.S. et al. E/Z(C=C)-Isomerization of enamines of 3-formyl-4-hydroxycoumarin induced by organic solvents. Russ Chem Bull 59, 1605–1611 (2010). https://doi.org/10.1007/s11172-010-0284-z

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  • DOI: https://doi.org/10.1007/s11172-010-0284-z

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