127667-06-5Relevant articles and documents
Displacement of Halogen of 2-Halogeno-Substituted Benzonitriles with Carbanions. Preparation of (2-Cyanoaryl)arylacetonitriles
Bech Sommer, Michael,Begtrup, Mikael,Boegesoe, Klaus Peter
, p. 4817 - 4821 (2007/10/02)
(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.