Prev. Article Next Article Table of Contents

Article

Conversion of an Aziridine to an Oxazolidinone Using a Salt and Carbon Dioxide in Water

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

PDF/HTML,
figures/images,
references and tables,
(where available)

Justin R. Wallace , Deborah L. Lieberman , Matthew T. Hancock and Allan R. Pinhas

Department of Chemistry, University of Cincinnati, Cincinnati, OH 45221-0172

J. Chem. Educ., 2005, 82 (8), p 1229

DOI: 10.1021/ed082p1229

Publication Date (Web): August 1, 2005

Section:

History, Education, and Documentation

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Heterocycles

View: Hi-Res PDF | PDF w/ Links

Citing Articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 1 ACS Journal articles (1 most recent appear below).

"Greening Up" the Suzuki Reaction
Evangelos Aktoudianakis , Elton Chan , Amanda R. Edward , Isabel Jarosz , Vicki Lee , Leo Mui , Sonya S. Thatipamala and Andrew P. Dicks
Journal of Chemical Education2008 85 (4), 555
- "Greening Up" the Suzuki Reaction
  Evangelos Aktoudianakis , Elton Chan , Amanda R. Edward , Isabel Jarosz , Vicki Lee , Leo Mui , Sonya S. Thatipamala and Andrew P. Dicks
  Journal of Chemical Education2008 85 (4), 555
  This article describes the rapid, green synthesis of a biaryl compound (4-phenylphenol) via a Pd(0)-catalyzed Suzuki cross-coupling reaction in water. Mild reaction conditions and operational simplicity makes this experiment especially amenable to both ...
  Abstract | Hi-Res PDF | PDF w/ Links