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The mechanism of the reaction at room temperature between an unactivated 2-alkyl aziridine and carbon dioxide to generate the corresponding oxazolidinone in glass has been studied. Theoretical calculations suggest that this reaction should not proceed at room temperature in the absence of a catalyst. In cases where a reaction was observed, kinetic studies show that the reaction displays a zero-order dependence with respect to aziridine, indicating that free aziridine is not involved in the rate-determining step. An ammonium salt generated in situ acts as a catalyst. The amount of this catalyst is diminutive, which prevented spectroscopic identification, and it is not readily removed from the starting material using chromatography. [ABSTRACT FROM AUTHOR]

Abstract: The conversion of an unactivated 2-alkylaziridine to the corresponding oxazolidinone generally requires a very high pressure of carbon dioxide, a high temperature, an expensive catalyst, and/or a long reaction time. Here, a new, high yield (over 95%), and highly regioselective (over 95%) conversion of an unactivated aziridine to an oxazolidinone is reported. This reaction is easy to perform because it requires a low pressure of carbon dioxide, low temperature, no co-solvent, and the catalyst is the salt ammonium iodide. [Copyright &y& Elsevier]