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Model Compounds of Ruthenium−Alkene Intermediates in Olefin Metathesis Reactions

Anderson, Donde R. and Hickstein, Daniel D. and O’Leary, Daniel J. and Grubbs, Robert H. (2006) Model Compounds of Ruthenium−Alkene Intermediates in Olefin Metathesis Reactions. Journal of the American Chemical Society, 128 (26). pp. 8386-8387. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20150310-115120338

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Abstract

The development of a model system to study ruthenium−olefin complexes relevant to the mechanism of olefin metathesis is reported. Upon addition of 1,2-divinylbenzene to (H_2IMes)(py_2)(Cl)_2Ru CHPh (H_2IMes = 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene), two ruthenium−olefin adducts are formed. On the basis of ^1H NMR spectroscopy experiments and X-ray crystallographic analysis, these complexes are assigned as side-bound isomers in which the olefin and H_2IMes ligands are coordinated cis to each other. The dynamic interconversion of these two ruthenium complexes was determined to have a barrier of 19.1 ± 0.1 kcal/mol.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja0618090DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja0618090PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja0618090PublisherSupporting Information
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2006 American Chemical Society. Received March 15, 2006. The authors thank Lawrence M. Henling and Dr. Michael W. Day for X-ray crystallography data, John Keith for invaluable assistance with theoretical calculations, and Materia, Inc. for generous donation of complex 2. D.R.A. was supported by NDSEG and NSF predoctoral fellowships. D.J.O. thanks the Mellon Foundation for financial support. This research was also supported by the National Science Foundation.
Funders:
Funding AgencyGrant Number
National Defense Science and Engineering Graduate (NDSEG) FellowshipUNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
Andrew W. Mellon FoundationUNSPECIFIED
Issue or Number:26
Record Number:CaltechAUTHORS:20150310-115120338
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20150310-115120338
Official Citation:Anderson, D. R., Hickstein, D. D., O'Leary, D. J., & Grubbs, R. H. (2006). Model Compounds of Ruthenium−Alkene Intermediates in Olefin Metathesis Reactions. Journal of the American Chemical Society, 128(26), 8386-8387. doi: 10.1021/ja0618090
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:55672
Collection:CaltechAUTHORS
Deposited By: Joanne McCole
Deposited On:10 Mar 2015 19:41
Last Modified:09 Mar 2020 13:19

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