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Synthesis of Cyclic Polybutadiene via Ring-Opening Metathesis Polymerization: The Importance of Removing Trace Linear Contaminants
Abstract
The synthesis of cyclic polybutadienes using ring-opening metathesis polymerization (ROMP) was accomplished. A cyclic Ru alkylidene catalyst, where a terminal ligand was covalently linked to the Ru alkylidene, was used to polymerize either 1,5-cyclooctadiene (COD) or 1,5,9-trans-cis-trans-cyclododecatriene (CDT). Trace amounts of an acyclic impurity, 4-vinylcyclohexene, found in the COD led to samples which were contaminated with linear polymer. In contrast, CDT, which was free of the impurity, afforded pure cyclic polymer. These results provide a convenient method for discerning samples of pure cyclic polymer from those which contain trace to large amounts of linear polymer. Furthermore, they emphasize the need to use monomers that are free of acyclic impurities when preparing cyclic polymers using ROMP.
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Citations
Cited by
Living ring-opening metathesis polymerization
Bielawski, C. W., & Grubbs, R. H. (2007) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2006.08.006 · Cited by 1,518
Self-citationGrubbs, R. H. (2004) · Tetrahedron · doi:10.1016/j.tet.2004.05.124 · Cited by 1,205
Self-citationThe synthesis, properties and potential applications of cyclic polymers
Haque, F. M., & Grayson, S. M. (2020) · Nature Chemistry · doi:10.1038/s41557-020-0440-5 · Cited by 417
Qiu, X.-P., Tanaka, F., & Winnik, F. M. (2007) · Macromolecules · doi:10.1021/ma071359b · Cited by 320
Cyclic polymers: Methods and strategies
Jia, Z., & Monteiro, M. J. (2012) · Journal of Polymer Science Part A: Polymer Chemistry · doi:10.1002/pola.25999 · Cited by 275
Metadata
- Authors
- Bielawski, C. W., Benitez, D., & Grubbs, R. H.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-06-18
- Volume
- 125
- Issue
- 28
- Pages
- 8424-8425
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2046581919
- Cited by
- 205
- References
- 0
- FWCI
- 5.40
- Type
- journal article
- Language
- en
- Open access
- closed
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- Bielawski, C. W., Benitez, D., & Grubbs, R. H. (2003). Synthesis of Cyclic Polybutadiene via Ring-Opening Metathesis Polymerization: The Importance of Removing Trace Linear Contaminants. Journal of the American Chemical Society. https://doi.org/10.1021/ja034524l
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