The Discovery-Oriented Approach to Organic Chemistry. 3. Rearrangement of cis- and trans-Stilbene Oxides with Boron Trifluoride Etherate. An Exercise in 1H NMR Spectroscopy for Sophomore Organic Laboratories

Epoxides, or oxiranes, are among the most versatile intermediates in organic synthesis. Yet very few examples of laboratory experiments involving reactions of epoxides are to be found in lab texts. We have developed a discovery-oriented laboratory experiment that involves the rearrangement of both c...

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Bibliographic Details
Published in:Journal of chemical education 2000-01, Vol.77 (1), p.79
Main Authors: Sgariglia, Erik A, Schopp, Regina, Gavardinas, Kostas, Mohan, Ram S
Format: Article
Language:English
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Summary:Epoxides, or oxiranes, are among the most versatile intermediates in organic synthesis. Yet very few examples of laboratory experiments involving reactions of epoxides are to be found in lab texts. We have developed a discovery-oriented laboratory experiment that involves the rearrangement of both cis- and trans-stilbene oxides with boron trifluoride etherate. The identity of the product can be easily determined by 1H NMR spectroscopy and, in case of the trans isomer, by preparation of the semicarbazone derivative as well. In spite of the simplicity of the experiment, the element of discovery ensures that student interest and enthusiasm are retained.
ISSN:0021-9584
1938-1328
DOI:10.1021/ed077p79