Synthesizing Stilbene by Olefin Metathesis Reaction Using Guided Inquiry To Compare and Contrast Wittig and Metathesis Methodologies
Year: 2018
Type: article
Abstract: 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 1 H 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.
Source: Journal of Chemical Education
Authors: Timothy J. Bannin, Partha P. Datta, Elizabeth T. Kiesewetter, Matthew K. Kiesewetter
Institutions: University of Rhode Island, Rhode Island College
Language: English
Subfield: Physical and Theoretical Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Award: G2656919733
OpenAlex ID: W2903748489