Addition reactions of conjugated double bonds. Part IV. The stereochemistry of cyanide ion addition to some αβ-unsaturated ketones and their π-allylpalladium derivatives

The stereochemistry of cyanide ion addition to 1-acetyl-4-t- butylcyclohexene involves preferred axial attack of the nucleophile. This ketone and related ones give π-allylpalladium derivatives in which the acetyl group is preferentially syn-substituted † on a terminal atom of the allylic system. The π-allylpalladium compounds react with cyanide ion to give mixtures of β-cyano-ketones similar to those given by the parent αβ-unsaturated ketones.