E/Z(C=C)-Isomerization of enamines of 3-formyl-4-hydroxycoumarin induced by organic solvents |
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| Authors: | V. F. Traven I. V. Ivanov V. S. Lebedev T. A. Chibisova B. G. Milevskii N. P. Solov’eva V. I. Polshakov G. G. Alexandrov O. N. Kazheva O. A. Dyachenko |
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| Affiliation: | 1.D. Mendeleev University of Chemical Technology of Russia,Moscow,Russian Federation;2.Center for Drug Chemistry,Moscow,Russian Federation;3.Institute of Problems of Chemical Physics,Russian Academy of Sciences,Chernogolovka, Moscow Region,Russian Federation;4.N. S. Kurnakov Institute of General and Inorganic Chemistry,Russian Academy of Sciences,Moscow,Russian Federation |
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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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