Abstract:
The kinetic isotope effects on the cyclization of substituted 2′-hydroxychalcones (R = 3-hydroxy, 4′-hydroxy, 4,4′- dihydroxy, 4′-hydroxy-4-nitro, 4-nitro, or 5′-methyl) into the corresponding substituted flavanones have been measured in water and/or methanol. The pronounced isotope effects observed are consistent with the slow rupture of a bond to hydrogen. The effect of the medium permittivity on the rate of cyclization of 2′-hydroxy, 2′,4-dihydroxy-, and 2′,4′-dihydroxychalcones have been also studied in several mixed solvents and the observed dependence is consistent with a reaction between one ion and one dipole. These results confirm a mechanism that involves general acid attack of the ionized form of the 2′-hydroxychalcones, concerted rotation through the CO-Cα- bond, and annellation to the flavanone.
Registro:
Documento: |
Artículo
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Título: | Cyclization of substituted 2′-hydroxychalcones to flavanones. Solvent and isotope effects |
Autor: | Furlong, J.J.P.; Sbarbati Nudelman, N. |
Filiación: | Cátedra de Quimica Fisica II, Facultad de Quimica, UniversidadNational de San Luis, 5700 San Luis, Argentina Departamento de Quimica Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
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Año: | 1988
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Número: | 7
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Página de inicio: | 1213
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Página de fin: | 1217
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DOI: |
http://dx.doi.org/10.1039/P29880001213 |
Título revista: | Journal of the Chemical Society, Perkin Transactions 2
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ISSN: | 1472779X
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1472779X_v_n7_p1213_Furlong |
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Citas:
---------- APA ----------
Furlong, J.J.P. & Sbarbati Nudelman, N.
(1988)
. Cyclization of substituted 2′-hydroxychalcones to flavanones. Solvent and isotope effects. Journal of the Chemical Society, Perkin Transactions 2(7), 1213-1217.
http://dx.doi.org/10.1039/P29880001213---------- CHICAGO ----------
Furlong, J.J.P., Sbarbati Nudelman, N.
"Cyclization of substituted 2′-hydroxychalcones to flavanones. Solvent and isotope effects"
. Journal of the Chemical Society, Perkin Transactions 2, no. 7
(1988) : 1213-1217.
http://dx.doi.org/10.1039/P29880001213---------- MLA ----------
Furlong, J.J.P., Sbarbati Nudelman, N.
"Cyclization of substituted 2′-hydroxychalcones to flavanones. Solvent and isotope effects"
. Journal of the Chemical Society, Perkin Transactions 2, no. 7, 1988, pp. 1213-1217.
http://dx.doi.org/10.1039/P29880001213---------- VANCOUVER ----------
Furlong, J.J.P., Sbarbati Nudelman, N. Cyclization of substituted 2′-hydroxychalcones to flavanones. Solvent and isotope effects. 1988(7):1213-1217.
http://dx.doi.org/10.1039/P29880001213