Synthesizing Stilbene by Olefin Metathesis Reaction Using Guided Inquiry to Compare and Contrast Wittig and Metathesis Methodologies
Date of Original Version
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.
Publication Title, e.g., Journal
Journal of Chemical Education
Bannin, Timothy J., Partha P. Datta, Elizabeth T. Kiesewetter, and Matthew K. Kiesewetter. "Synthesizing Stilbene by Olefin Metathesis Reaction Using Guided Inquiry to Compare and Contrast Wittig and Metathesis Methodologies." Journal of Chemical Education 96, 1 (2019): 143-147. doi: 10.1021/acs.jchemed.8b00313.