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RESEARCH PRODUCT

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

Stefan HilfRobert H. GrubbsAndreas F. M. Kilbinger

subject

Magnetic Resonance SpectroscopyTime FactorsPolymerschemistry.chemical_elementDioxolesAlkenesMetathesisBiochemistryRutheniumCatalysisLactoneschemistry.chemical_compoundColloid and Surface ChemistryPolymer chemistryOrganometallic CompoundsRing-opening metathesis polymerisationMolecular StructureTransition metal carbene complexStereoisomerismGeneral ChemistryROMPReference StandardsRutheniumPolymerizationchemistrySpectrometry Mass Matrix-Assisted Laser Desorption-IonizationMethaneCarbeneAcyclic diene metathesis

description

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 (1)H NMR spectroscopy, MALDI-ToF mass spectrometry, and end-group derivatization.

yearjournalcountryeditionlanguage
2008-08-20Journal of the American Chemical Society
https://doi.org/10.1021/ja8022863