Alumina, impregnated with sodium cyanide

A paper by Regen and co-workers reports on a convenient synthesis of nitriles which we believe to have application to other displacement reactions. In this procedure, alumina is impregnated with sodium cyanide. This solid is stirred with a solution of an alkyl halide... 

Aryl cyanation. Reaction of iodobenzene with sodium cyanide in the presence of 10 mole % of Pd(0) affords only a 5% yield of benzonitrile. If the sodium cyanide is impregnated on alumina the reaction proceeds in quantitative yield. In the same reaction with aryl bromides higher yields obtain when alumina is present as a co-catalyst rather than as a support. 

Aromatic nitriles are now also available in good yields from aryl iodides by reaction with sodium cyanide impregnated on alumina/ from primary aralkyl-amines by oxidation with a potassium ruthenate-potassium persulphate system/ ... 

Alkyl nitriles are also prepared from alkyl halides with sodium cyanide impregnated on alumina and with cyanide ion in the presence of polystyrene-bound n-propyltributylphosphonium bromide, and by hydrocyanation of alkenes and alkynes. ... 

---