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
J. Chem. Educ., 2008, 85 (9), p 1274
DOI: 10.1021/ed085p1274
Publication Date (Web): September 1, 2008

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.

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  • Received: August 03, 2009

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