Ultrasonic effects on electroorganic processes. Part 22. Cathodic crossed hydrocoupling of acetone with acrylonitrile

The ultrasonic effects on the cathodic-crossed hydrocoupling of acetone with acrylonitrile were examined. The total current efficiency of all products in the cathodic reduction of a mixture of acetone and acrylonitrile was little influenced by ultrasonic irradiation, while the product selectivity for crossed hydrocoupling products formed in the cathodic reduction was significantly increased by irradiation. This ultrasonic effect could be rationalized as being due to mass-transport promotion of acrylonitrile molecules as an electrophile to the cathode surface from the bulk of the electrolytic solution by the ultrasonic irradiation. Thus, the ultrasonic effect can be purposively applied to control the product selectivity in the crossed coupling reaction.