Collect. Czech. Chem. Commun. 1985, 50, 365-374

Mechanism of acetoacetylation of substituted anilines

Jiří Knížek, Erhard Lejdar and Pavel Vetešník

Department of Organic Chemistry, Institute of Chemical Technology, 532 10 Pardubice


Kinetics have been studied of the reaction of diketene with substituted anilines, and the reaction rate has been found to depend on relative permittivity of the system. The rate and equilibrium constants have been calculated by combination of rate and equilibrium relations with the relation by Amis; the constants correlate with the Hammett substituent constants. The reaction does not proceed as a simple bimolecular process. A reaction mechanism has been suggested.