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

• Erik A. Sgariglia ^[1] ; Regina Schopp ^[1] ; Kostas Gavardinas ^[1] ; Ram S. Mohan ^[1]
  1. [1] Illinois Wesleyan University

     Illinois Wesleyan University

     Township of Bloomington City, Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 77, Nº 1 (January), 2000, págs. 79-79
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • 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.