The C-Arylation of α-Cyano Esters and Malononitriles by Aryllead(IV) Triacetates

Abstract

The arylation of soft carbon nucleophiles by aryllead (IV) triacetates has been extended to α- cyano esters and malononitriles. Arylation did not occur with the parent compounds, ethyl cyanoacetate and malononitrile, but in both series monosubstituted compounds reacted to give α-aryl derivatives in synthetically useful yields. A study of the effect of some tertiary aromatic amines and dimethyl sulfoxide, substances which complex with lead(IV), has been carried out, and in two cases the influence of bulky α- substituents has been examined.