Synthesizing Stilbene by Olefin Metathesis Reaction Using Guided Inquiry To Compare and Contrast Wittig and Metathesis Methodologies

• Timothy J. Bannin ^[1] ; Partha P. Datta ^[1] ; Elizabeth T. Kiesewetter ^[2] ; Matthew K. Kiesewetter ^[1]
  1. [1] University of Rhode Island

     University of Rhode Island

     Town of South Kingstown, Estados Unidos

     
  2. [2] Rhode Island College

     Rhode Island College

     City of Providence, Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 96, Nº 1, 2019, págs. 143-147
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • In this experiment, students are asked to conduct a catalytic cross-metathesis experiment and compare this reaction to the Wittig reaction within the confines of green chemistry. Students synthesize stilbene from styrene using Grubbs second-generation catalyst. Products can be minimally characterized by IR spectroscopy and melting point, but using 1H NMR spectroscopy is preferred. Students find that the Wittig reaction is selective for cis-stilbene while the metathesis reaction produces >98% trans-stilbene. Students determine the cis/trans selectivity, turnover number, and maximum turnover frequency of the reaction. The experiment is conducted alongside the synthesis of stilbene using Wittig chemistry from a published procedure.