Displacement of Halogen of 2-Halogeno-Substituted Benzonitriles with Carbanions. Preparation of (2-Cyanoaryl)arylacetonitriles

Article abstract of DOI:10.1021/jo00303a011

(2-Cyanoaryl)arylacetonitriles are obtained by displacement of halogen of 2-halobenzonitriles with phenylacetonitrile anions.The method also applies to a number of heteroaromatics with ortho-situated halogen and cyano groups and to heteroarylacetonitrile anions.The anions were generated by using potassium tert-butoxide or potassium carbonate.Calculated electron densities of the electrophilic centers reflect the reactivity in the displacement reaction.The calculations indicate that the potassium ion complexes with the cyano group of the 2-halobenzonitriles in nonpolar solvents, thus promoting competitive addition of the anion to the cyano group.Carbanions derived from acids with pKa ca. 19-23 similarly displaced the halogen of 2-halobenzonitriles.