Factors Affecting Reaction Kinetics
The Dakin oxidation has two rate-limiting steps: nucleophilic addition of hydroperoxide to the carbonyl carbon and -aryl migration. Therefore, the overall rate of oxidation is dependent on the nucleophilicity of hydroperoxide, the electrophilicity of the carbonyl carbon, and the speed of -aryl migration. The alkyl substituents on the carbonyl carbon, the relative positions of the hydroxyl and carbonyl groups on the aryl ring, the presence of other functional groups on the ring, and the reaction mixture pH are four factors that affect these rate-limiting steps.
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