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Efficient Synthesis of Geminal-Dialkyl Dienes for Olefin Metathesis Polymerization

Wolf, William J. and Li, Jiaming and Jones, Simon C. and Stoltz, Brian M. and Grubbs, Robert H. (2020) Efficient Synthesis of Geminal-Dialkyl Dienes for Olefin Metathesis Polymerization. Macromolecules, 53 (18). pp. 7803-7809. ISSN 0024-9297. PMCID PMC8297823. doi:10.1021/acs.macromol.0c01606.

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A robust synthesis of gem-dialkyl acyclic diene monomers has been developed. This route is scalable, flexible, and biorenewable, allowing for the production of a wide range of diene monomers of different lengths and different gem-dialkyl substitutions starting from unsaturated esters derived from seed oils. The metathesis polymerization of these monomers and the hydrogenation of the resulting polyolefins lead to telechelic gem-dialkyl polyethylenes, which can be used as elastomers in the synthesis of polyurethanes and other block polymers.

Item Type:Article
Related URLs:
URLURL TypeDescription CentralArticle
Wolf, William J.0000-0001-6755-8920
Li, Jiaming0000-0001-6646-5693
Jones, Simon C.0000-0002-1952-3720
Stoltz, Brian M.0000-0001-9837-1528
Grubbs, Robert H.0000-0002-0057-7817
Alternate Title:An Efficient Synthesis of Geminal-Dialkyl Dienes for Olefin Metathesis Polymerization
Additional Information:© 2020 American Chemical Society. Received: July 13, 2020; Revised: August 25, 2020; Published: September 10, 2020. W.J.W. gratefully acknowledges the support of the Arnold O. Beckman postdoctoral fellowship. B.M.S. thanks the NIH-GMS (R01GM080269) for generous support. We thank Mr. Doug Rose and Prof. Heather Maynard (UCLA) for use of their DSC instrument, and Prof. Marc Hillmyer (UMN) for sharing the details of the synthesis of 38. We are grateful to Steve Cohen and Elevance Renewable Sciences for their donation of methyl 9-decenoate. Author Contributions. W.J.W. and J. L. contributed equally. The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript. The authors declare the following competing financial interest(s): A provisional patent regarding this work (CIT-8317-P) has been filed.
Funding AgencyGrant Number
Arnold and Mabel Beckman FoundationUNSPECIFIED
Subject Keywords:Hydrocarbons, Organic compounds, Monomers, Ketones, Polymers
Issue or Number:18
PubMed Central ID:PMC8297823
Record Number:CaltechAUTHORS:20200911-133138265
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Official Citation:Efficient Synthesis of Geminal-Dialkyl Dienes for Olefin Metathesis Polymerization. William J. Wolf, Jiaming Li, Simon C. Jones, Brian M. Stoltz, and Robert H. Grubbs. Macromolecules 2020 53 (18), 7803-7809; DOI: 10.1021/acs.macromol.0c01606
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:105352
Deposited By: George Porter
Deposited On:14 Sep 2020 14:05
Last Modified:22 Nov 2021 23:30

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