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  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > September  >
In the Laboratory
Green Chemistry
The Discovery-Oriented Approach to Organic Chemistry. 7. Rearrangement of trans-Stilbene Oxide with Bismuth Trifluoromethanesulfonate and Other Metal Triflates
A Microscale Green Organic Chemistry Laboratory Experiment
James E. Christensen, Matthew G. Huddle, Jamie L. Rogers, Herbie Yung, and Ram S. Mohan
Department of Chemistry, Illinois Wesleyan University, Bloomington, IL 61701
Cover
September 2008
Vol. 85 No. 9
p. 1274
Abstract
Although green chemistry principles are increasingly stressed in the undergraduate curriculum, there are only a few lab experiments wherein the toxicity of reagents is taken into consideration in the design of the experiment. We report a microscale green organic chemistry laboratory experiment that illustrates the utility of metal triflates, especially bismuth triflate as a Lewis acid catalyst. Bismuth compounds are especially attractive for use as catalysts in organic synthesis because of their remarkably low toxicity, low cost, and ease of handling.
Supplement
Student handouts; Instructor notes including the 1H NMR spectra
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Citation
Christensen, James E.; Huddle, Matthew G.; Rogers, Jamie L.; Yung, Herbie; Mohan, Ram S. J. Chem. Educ. 2008, 85, 1274.
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Keywords
Catalysis; Epoxides; Green Chemistry; Hands-On Learning / Manipulatives; Inquiry-Based / Discovery Learning; Laboratory Instruction; Lewis Acids / Bases; Mechanisms of Reactions; Microscale Lab; NMR Spectroscopy; Organic Chemistry; Problem Solving / Decision Making; Second-Year Undergraduate
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History
Created:
Last Updated:
8/4/2008
8/4/2008
 Caution! 
Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
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