Abstract
It is known that acyloin, alpha-hydroxyketone, undergoes intramolecular rearrangement under acidic and basic conditions. The hydrogen-transfer reactions of acyloin derivatives in aqueous solvent were experimentally studied to reveal the time course of chemical reaction and solvation-desolvation event. Acyloin derivatives were allowed to react with potassium hydroxide in 70% (v/v) aqueous methanol at 25 degrees. The hydrogen transfer reaction was observed under the nitrogen atmosphere without side reactions. The equilibrium constants of the reactions were measured by using NMR, and the rates of the reactions were measured by using UV spectrometer. The reaction mechanisms will be discussed on the basis of substituent effects.
