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  Home > JCE Print > Journal of Chemical Education > Issues > 2005  > August  >
In the Laboratory
Conversion of an Aziridine to an Oxazolidinone Using a Salt and Carbon Dioxide in Water
Justin R. Wallace, Deborah L. Lieberman, Matthew T. Hancock, and Allan R. Pinhas
Department of Chemistry, University of Cincinnati, Cincinnati, OH 45221-0172
Cover
August 2005
Vol. 82 No. 8
p. 1229
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.
Supplement
1H NMR data, a proposed mechanism, a compete list of references, and notes for the instructor are available.
*  Contents JCE2005p1229W.doc (Microsoft Word)
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JCE2005p1229W.pdf

JCE2005p1229W.zip
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*  Citation
 Wallace, Justin R.; Lieberman, Deborah L.; Hancock, Matthew T.; Pinhas, Allan R. J. Chem. Educ. 2005 82 1229.
*  Keywords
 Aqueous Solution Chemistry; Constitutional Isomers; Hands-On Learning / Manipulatives; Heterocycles; Laboratory Instruction; Mechanisms of Reactions; NMR Spectroscopy; Organic Chemistry; Problem Solving / Decision Making; Quantitative Analysis; Second-Year Undergraduate; Synthesis
*  History
 Created:
Last Updated:		 July 5, 2005
July 8, 2005
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