3471-13-4Relevant academic research and scientific papers
Kinetic Studies of Fast Equilibrium by Means of High-Performance Liquid Chromatography. XVII. Separation of Tautomers of 1,3-Cyclohexanediones
Moriyasu, Masataka,Kato, Atsushi,Hashimoto, Yohei
, p. 2955 - 2956 (1988)
Tautomers of 1,3-cyclohexanediones have been separated by means of low-temperature high-performance liquid chromatography (HPLC).The ratios of keto- and enol-forms have been found to be highly solvent dependent, which is explained in terms of solute-solvent and solute-solute hydrogen bonding.
Alkylation of methylene-active compounds with halo acetals and hydrolysis of the alkylation products
Ismailov,Yusubov,Sadykhova,Gasymov,Ibragimova,Mamedov
, p. 1390 - 1393 (2016/11/29)
A preparative procedure has been proposed for the alkylation of CH acids with halo acetals and hydrolysis of the alkylation products to furan derivatives and lactones.
Solvent Effects on Keto-Enol Equilibria: Tests of Quantitative Models
Mills, Sander G.,Beak, Peter
, p. 1216 - 1224 (2007/10/02)
The effect of solvent on the equilibrium constants between selected keto-enol isomer pairs has been determined.The protomeric systems studied are 5,5-dimethyl-1,3-cyclohexanedione (1), 2-methyl-1,3-cyclohexanedione (3), 3-oxabicyclo-2,9-dioxononane (5), 2,4-pentanedione (7), ethyl 3-oxobutanoate (9), and 9-anthracenone (11).A wide variety of theoretical and empirical solvation parameters have been tested in a multiparameter linear free energy format to model the changes in equilibria.The most successful correlations are obtained with the Kamlet-Taft polarity-polarizability and hydrogen-bonding terms, although the Swain A and B factors have advantages in same cases.In general, for the isomer pairs in which the enol cannot form an internal hydrogen bond (1-2, 3-4, and 11-12), the equilibria appear to be controlled almost completely by the hydrogen-bonding basicity of the solvent.For the isomer pairs 5-6, 7-8, and 9-10, in which intramolecular hydrogen bonding is possible, the polarity-polarizability effect dominates, although differential stabilization of the isomers by hydrogen bonding remains significant.
