Reactions of Activated Olefinic and Aromatic Systems with Cyanide Ion and with Certain Carbanions in Aprotic Solvents

The report briefly reviews results and publications from a research study on anion attack on conjugated systems. In dipolar aprotic solvents (DMSO, DMF) heavily arylated olefinic compounds having one or more double bonds activated by conjugation with the aromatic systems undergo reversible addition of cyanide ion to give carbanions which can be transformed into other substances, including the products of cyanation and hydrocyanation of the original hydrocarbons. Aromatic nitriles, particularly those containing polynuclear aromatic systems, also undergo addition of cyanide ion in a process which is useful in synthesis, including the synthesis of C-14 labelled nitriles. Aromatic ketones react with cyanide ion similarly but less readily, and aromatic nitro compounds are more reactive than nitriles and can be converted to a number of further transformation products. (Modified author abstract)