Nucleophilic addition reactions of cyclohexylidenemalononitrile occur mainly in the conjugate manner.When the nucleophile was the hydride anion, selective reduction of the carbon-carbon double bond only took place at low temperatures. At ambient temperature, reduction was more estensive, resulting in ah eneaminonitrile. During the alkylation of cyclohexylidenemalononitrile, reduction by alkylmagnesium bromides was favored by the presence of a S-hydrogen on the alkyl group, and by the degree of branching in the latter; arylmagnesium bromides were however, less reactive. Alkaline hydrolysis of the Grignard adducts did not take place readily. The stepwise nature of this process was clearly demonstrated by the fact that, the substrates were hydrated to varying extents, depending on the steric environment of the cyano groups.Ball State UniversityMuncie, IN 47306