Synthesis of Poly(methylphenyl)acetonitriles by the Aryne Reaction

Abstract

Several 2-(arylmethyl) derivatives of 3,6-dimethyl- and 3,4,5,6-tetramethylbenzonitriles have been prepared in good yields most likely by a tandem addition-rearrangement reaction of the appropriate bromoarene and arylacetonitrile under aryne-forming conditions. Additionally, several 2-aryl-2-(1,4-dimethyl-2-naphthyl)acetonitriles were obtained by the usual aryne mechanism from the reaction of 2-bromo-1,4-dimethylnaphthalene and arylacetonitriles with lithium tetramethylpiperidide.