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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.
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Ando et al. (1984) studied this question.
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