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Nobel Chemistry in the Laboratory: Synthesis of a Ruthenium Catalyst for Ring-Closing Olefin Metathesis
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Abstract
An experiment for the upper-level undergraduate laboratory is described in which students synthesize a ruthenium olefin metathesis catalyst, then use the catalyst to carry out the ring-closing metathesis of diethyl diallylmalonate. The olefin metathesis reaction was the subject of the 2005 Nobel Prize in chemistry. The catalyst chosen for this experiment is the ruthenium alkylidene complex that is most practical to synthesize in an undergraduate laboratory for reasons of time, safety, and cost of materials. The three-step synthesis of (PCy3)2Cl2Ru(=CH–CH=CMe2) from RuCl3·H2O goes through [(COD)RuCl2]x and Ru(H)(H2)(Cl)(PCy3)2 as intermediates. The latter complex is air sensitive, giving students the opportunity to learn Schlenk techniques. The ring-closed product is purified by column chromatography, and the catalyst and the ring-closed product are characterized by NMR spectroscopy.
Keywords (Audience):
Upper-Division UndergraduateKeywords (Domain):
Inorganic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
AlkynesCiting Articles
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This article has been cited by 3 ACS Journal articles (3 most recent appear below).
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C. Eric BallardJournal of Chemical Education2011 Article ASAPAlthough transition-metal-catalyzed reactions are important in contemporary organic chemistry, relatively few resources for the second-year organic chemistry curriculum discuss the subject. The inquiry-based experiment described here, an iron-catalyzed ...
Ring-Closing Metathesis: An Advanced Guided-Inquiry Experiment for the Organic Laboratory
Hala G. Schepmann and Michelle MynderseJournal of Chemical Education2010 87 (7), 721-723Ring-Closing Metathesis: An Advanced Guided-Inquiry Experiment for the Organic Laboratory
Hala G. Schepmann and Michelle MynderseJournal of Chemical Education2010 87 (7), 721-723The design and implementation of an advanced guided-inquiry experiment for the organic laboratory is described. Grubbs’s second-generation catalyst is used to effect the ring-closing metathesis of diethyl diallylmalonate. The reaction is carried out under ...
Two Undergraduate Experiments in Organic Polymers: The Preparation of Polyacetylene and Telechelic Polyacetylene via Ring-Opening Metathesis Polymerization
Eric J. Moorhead and Anna G. WenzelJournal of Chemical Education2009 86 (8), 973Two Undergraduate Experiments in Organic Polymers: The Preparation of Polyacetylene and Telechelic Polyacetylene via Ring-Opening Metathesis Polymerization
Eric J. Moorhead and Anna G. WenzelJournal of Chemical Education2009 86 (8), 973The ruthenium-catalyzed ring-opening metathesis polymerization of 1,3,5,7-cyclooctatetraene (COT) to produce polyacetylene and a telechelic polymer of polyacetylene is described in a series of two experiments for the undergraduate laboratory. In the first ...
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- Received: August 03, 2009
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CHPh)(PCy3)22. These air- and water-tolerant complexes were shown to exhibit an increased ring-closing metathesis ...
