U.S. flag

An official website of the United States government, Department of Justice.

Diastereofacial selectivity of a-aminonitrile formation from substituted cyclohexanones

NCJ Number
Date Published
September 2023

The author’s goal for this research project was to understand the extent of the diastereofacial selectivity in the formation of α-aminonitriles from substituted cyclohexanones, with different combinations of reactants.


The formation of α-aminonitriles from substituted cyclohexanones exhibits diastereofacial selectivity resulting in unequal amounts of the two possible geometric isomers. The degree of selectivity increases with the nature of the substitution on the cyclohexyl ring indicating that this likely results from the degree to which the substitution can ‘lock’ the conformation of the cyclohexyl ring into the most stable conformation. The ratio of trans:cis isomers seen for the reaction of 4-substituted cyclohexanones with dimethylamine hydrochloride and potassium cyanide in water were 92:8 for 4-phenyl, 81:19 for 4-t-butyl, and 62:38 for 2-methyl. Varying the size of the amino group substituents did not have a dramatic effect on the selectivity that was observed. Publisher Abstract Provided

Date Published: September 1, 2023