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  Home > JCE Print > Journal of Chemical Education > Issues > 2007  > December  >
In the Laboratory
Nobel Chemistry in the Laboratory: Synthesis of a Ruthenium Catalyst for Ring-Closing Olefin Metathesis
An Experiment for the Advanced Inorganic or Organic Laboratory
George E. Greco
Department of Chemistry, Goucher College, Baltimore, MD 21204
Cover
December 2007
Vol. 84 No. 12
p. 1995

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.
Supplement
Student handout, detailed notes for the instructors including details on the logistics of scheduling this experiment, list of all of the equipment and chemicals needed for this experiment, and NMR spectra are available
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Contents
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Citation
Greco, George E. J. Chem. Educ. 2007, 84, 1995.
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Keywords
Alkenes; Alkynes; Catalysis; Coordination Compounds; Hands-On Learning / Manipulatives; Inorganic Chemistry; Interdisciplinary / Multidisciplinary; Laboratory Instruction; NMR Spectroscopy; Organic Chemistry; Organometallics; Synthesis; Transition Elements; Upper-Division Undergraduate
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History
Created:
Last Updated:
10/25/2007
10/31/2007
 Caution! 
Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
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