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.
The conversion of unactivated 2‐alkyl or 2‐aryl aziridines (I) and (IV) with CO2 (II) generates the corresponding oxazolidones (III) and (V) without the need of catalysis or solvent in high yields, especially when using high speed ball milling.
Key indicatorsSingle-crystal X-ray study T = 150 K Mean (C-C) = 0.002 Å R factor = 0.023 wR factor = 0.061 Data-to-parameter ratio = 14.7For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e. # 2005 International Union of Crystallography Printed in Great Britain -all rights reserved The title complex, C 14 H 13 BrClNO, adopts a helical motif built up from intermolecular O-HÁ Á ÁO interactions with a repeat distance of 8.4 Å . Further assembly of the helices forms a parallel square grid array reminiscent of apolar peptide extended packing motifs.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.