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Published June 30, 2010 | Supplemental Material + Accepted Version
Journal Article Open

Nonproductive Events in Ring-Closing Metathesis Using Ruthenium Catalysts


The relative TONs of productive and nonproductive metathesis reactions of diethyl diallylmalonate are compared for eight different ruthenium-based catalysts. Nonproductive cross metathesis is proposed to involve a chain-carrying ruthenium methylidene. A second more-challenging substrate (dimethyl allylmethylallylmalonate) that forms a trisubstituted olefin product is used to further delineate the effect of catalyst structure on the relative efficiencies of these processes. A steric model is proposed to explain the observed trends.

Additional Information

© 2010 American Chemical Society. Received April 6, 2010. Publication Date (Web): June 2, 2010. The NIH (K99GM084302 to I.C.S., 5RO1GM-31332 to R.H.G.) for generous financial support, Hosea Nelson and Brian M. Stoltz (Caltech) for assistance with and use of their TOF-MS instrument, and Scott Virgil (Caltech Center for Catalysis and Chemical Synthesis) for assistance with automation and analytical equipment. Supporting Information Available: Experimental procedures and details of quantitative analysis. This material is available free of charge via the Internet at http://pubs.acs.org.

Attached Files

Accepted Version - nihms211085.pdf

Supplemental Material - ja1029045_si_001.pdf


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