Iron Carbonyl Promoted Conversion of an Aziridine and an Amine Oxide to a 1,2-Diamine

Abstract

The conversion of an aziridine to a 1,2-diamine using an iron carbonyl complex and an amine oxide is studied. We have found that when the aziridine is substituted by only alkyl groups, it is the less substituted carbon−nitrogen bond that is broken, whereas, when the aziridine is substituted by a phenyl group at either the nitrogen or the carbon, it is the more substituted carbon−nitrogen bond that is broken. With a 2,3-disubstituted aziridine, the reaction proceeds with net retention of stereochemistry. Because the nitrogen in the amine oxide is trisubstituted and the same nitrogen in the product is disubstituted, various amine oxides have been tried to determine the preference for which group will be removed. We have shown that the intermediate iron complex will react with an iminium salt to give the exact same product as is obtained from the corresponding amine oxide.