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End Capping Ring-Opening Olefin Metathesis Polymerization Polymers with Vinyl Lactones

Hilf, Stefan and Grubbs, Robert H. and Kilbinger, Andreas F. M. (2008) End Capping Ring-Opening Olefin Metathesis Polymerization Polymers with Vinyl Lactones. Journal of the American Chemical Society, 130 (33). pp. 11040-11048. ISSN 0002-7863. doi:10.1021/ja8022863.

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The selective placement of a functional group at the chain end of a ring-opening metathesis polymer using ruthenium carbene initiators has been a significant limitation. Here we demonstrate a highly effective and facile end-capping technique for ROMP with living ruthenium carbene chain ends using single-turnover olefin metathesis substrates. Vinylene carbonate and 3H-furanone are introduced as functionalization and termination agents for the ruthenium-initiated ring-opening metathesis polymerization. This leads directly to the formation of functional polymer end groups without further chemical transformation steps. Aldehyde and carboxylic acid end groups can be introduced by this new method which involves the decomposition of acyl carbenes to ruthenium carbides. The high degrees of chain-end functionality obtained are supported by ^1H NMR spectroscopy, MALDI-ToF mass spectrometry, and end-group derivatization.

Item Type:Article
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Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2008 American Chemical Society. Received March 28, 2008. Publication Date (Web): July 23, 2008. The authors thank Florian Wolf for MALDI-ToF MS measurements, Daniel Wenzlik for laboratory assistance and Materia, Inc. for generous catalyst support. S.H. thanks the POLYMAT Graduate School of Excellence (University of Mainz) for funding. A.F.M.K. thanks the Deutsche Forschungsgemeinschaft (DFG) for financial support.
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University of MainzUNSPECIFIED
Deutsche Forschungsgemeinschaft (DFG)UNSPECIFIED
Issue or Number:33
Record Number:CaltechAUTHORS:20170510-124358237
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Official Citation:End Capping Ring-Opening Olefin Metathesis Polymerization Polymers with Vinyl Lactones Stefan Hilf, Robert H. Grubbs, and Andreas F. M. Kilbinger Journal of the American Chemical Society 2008 130 (33), 11040-11048 DOI: 10.1021/ja8022863
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:77345
Deposited By: Tony Diaz
Deposited On:16 May 2017 20:02
Last Modified:15 Nov 2021 17:30

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