Ultrasonic irradiation of a mixture of benzyl bromide, potassium cyanide, and alumina in an aromatic solvent yields benzyl cyanide, whereas mechanical agitation gives the Friedel–Crafts type product; sonication changes the main reaction pathway from aromatic electrophilic to aliphatic nucleophilic substitution.
T. Ando, S. Sumi, T. Kawate, J. Ichihara (née Yamawaki) and T. Hanafusa, J. Chem. Soc., Chem. Commun., 1984, 439 DOI: 10.1039/C39840000439
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