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

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.