Abstract
Among the aryl-aliphatic nitriles subject to alkylation, phenylacetonitrile is especially reactive and its methylene hydrogens are readily replaced by one or two alkyl groups. The benzylation of this substance is most commonly performed with benzyl chloride in the presence of finely powdered sodium amide in an inert solvent. The preliminary communication from this laboratory reported several examples of benzylation of phenylacetonitrile and related nitriles (I) by means of benzyl alcohol and sodium. (Chart 1). The present paper is concerned with the detailed study of the reaction and additional comments about the mechanism.
