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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

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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

Section:

History, Education, and Documentation

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

Green Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Catalysis

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

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  Victoria Polito, Christian S. Hamann and Ian J. Rhile
  Journal of Chemical Education2010 87 (9), 969-970
  In this discovery laboratory, students performed electrophilic aromatic substitution reactions between 1,4-dimethoxybenzene and either 2-methyl-2-butanol or 3-methyl-2-butanol with sulfuric acid as a catalyst. The carbocation from 3-methyl-2-butanol ...
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