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. doi:10.1021/ja0618090. 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.

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Article

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URL	URL Type	Description
http://dx.doi.org/10.1021/ja0618090	DOI	Article
http://pubs.acs.org/doi/abs/10.1021/ja0618090	Publisher	Article
http://pubs.acs.org/doi/suppl/10.1021/ja0618090	Publisher	Supporting Information

ORCID:

Author	ORCID
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 Agency	Grant Number
National Defense Science and Engineering Graduate (NDSEG) Fellowship	UNSPECIFIED
NSF Predoctoral Fellowship	UNSPECIFIED
Andrew W. Mellon Foundation	UNSPECIFIED

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DOI:

10.1021/ja0618090

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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

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55672

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CaltechAUTHORS

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Deposited On:

10 Mar 2015 19:41

Last Modified:

10 Nov 2021 20:48

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