E/Z(C=C)-Isomerization of enamines of 3-formyl-4-hydroxycoumarin induced by organic solvents
V.F. Traven’
1
,
I.V. Ivanov
1
,
V. S. LEBEDEV
1
,
T.A. Chibisova
1
,
B G Milevskii
1
,
N P Soloveva
1
,
V I Polshakov
2
,
G.G. Alexandrov
3
,
O N Kazheva
4
,
O. A. Dyachenko
4
2
Center for Drug Chemistry, Moscow, Russian Federation
|
Publication type: Journal Article
Publication date: 2010-08-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
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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Traven’ V. et al. E/Z(C=C)-Isomerization of enamines of 3-formyl-4-hydroxycoumarin induced by organic solvents // Russian Chemical Bulletin. 2010. Vol. 59. No. 8. pp. 1605-1611.
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Traven’ V., Ivanov I., LEBEDEV V. S., Chibisova T., Milevskii B. G., Soloveva N. P., Polshakov V. I., Alexandrov G., Kazheva O. N., Dyachenko O. A. E/Z(C=C)-Isomerization of enamines of 3-formyl-4-hydroxycoumarin induced by organic solvents // Russian Chemical Bulletin. 2010. Vol. 59. No. 8. pp. 1605-1611.
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TY - JOUR
DO - 10.1007/s11172-010-0284-z
UR - http://link.springer.com/10.1007/s11172-010-0284-z
TI - E/Z(C=C)-Isomerization of enamines of 3-formyl-4-hydroxycoumarin induced by organic solvents
T2 - Russian Chemical Bulletin
AU - Traven’, V.F.
AU - Ivanov, I.V.
AU - LEBEDEV, V. S.
AU - Chibisova, T.A.
AU - Milevskii, B G
AU - Soloveva, N P
AU - Polshakov, V I
AU - Alexandrov, G.G.
AU - Kazheva, O N
AU - Dyachenko, O. A.
PY - 2010
DA - 2010/08/01
PB - Springer Nature
SP - 1605-1611
IS - 8
VL - 59
SN - 1066-5285
SN - 1573-9171
ER -
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BibTex (up to 50 authors)
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@article{2010_Traven’,
author = {V.F. Traven’ and I.V. Ivanov and V. S. LEBEDEV and T.A. Chibisova and B G Milevskii and N P Soloveva and V I Polshakov and G.G. Alexandrov and O N Kazheva and O. A. Dyachenko},
title = {E/Z(C=C)-Isomerization of enamines of 3-formyl-4-hydroxycoumarin induced by organic solvents},
journal = {Russian Chemical Bulletin},
year = {2010},
volume = {59},
publisher = {Springer Nature},
month = {aug},
url = {http://link.springer.com/10.1007/s11172-010-0284-z},
number = {8},
pages = {1605--1611},
doi = {10.1007/s11172-010-0284-z}
}
Cite this
MLA
Copy
Traven’, V.F., et al. “E/Z(C=C)-Isomerization of enamines of 3-formyl-4-hydroxycoumarin induced by organic solvents.” Russian Chemical Bulletin, vol. 59, no. 8, Aug. 2010, pp. 1605-1611. http://link.springer.com/10.1007/s11172-010-0284-z.
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