No abstract

An undergraduate laboratory experiment that allows for optimization of experimental reaction conditions for the conversion of a readily-available aziridine to the corresponding oxazolidinone using only carbon dioxide and a salt in water is discussed. A variety of salts were used to determine their effect on the reaction. In all cases, either no reaction occurred or a high yield of product was obtained. Ring opening of the less substituted carbon–nitrogen bond predominates. This experiment allows students to optimize reaction conditions to obtain predominantly one of two regioisomers.

No 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.

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