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The conversion of an aziridine to a 1,2-diamine using lithium iodide and an iminium salt is discussed. We have found that when the aziridine is substituted by only alkyl groups, it is the less substituted carbon&z.sbnd;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&z.sbnd;nitrogen bond that is broken. For a 2,3-disubstituted aziridine, the reaction sequence goes with net retention of stereochemistry. [Copyright &y& Elsevier]

The conversion of an aziridine to the corresponding oxazolidinone using only carbon dioxide and a catalytic amount of lithium iodide is discussed. In all cases, either no reaction occurred or a high yield of product was obtained. HMPA has been added to the reaction mixture, as needed, to drastically improve the regioselectivity. Net retention of stereochemistry between the starting aziridine and the product oxazolidinone was observed. [Copyright &y& Elsevier]