Chain Transfer during the Aqueous Ring-Opening Metathesis Polymerization of 7-Oxanorbornene Derivatives

Marcia B. France, Robert H. Grubbs, Dominic V. McGrath, Rocco A. Paciello

Research output: Contribution to journalArticle

55 Scopus citations

Abstract

Ring-opening metathesis polymerization (ROMP) of exo,exo-5,6-bis(methoxymethyl)-7-oxabicyclo[2.2.1]hept-2-ene (3) catalyzed by RuII(H2O)6(tosh (tos = p-toluenesulfonate) (1) in the presence of terminal acyclic olefins such as 3-buten-l-ol and methyl acrylate affords low molecular weight polymeric materials. Analysis of these oligomer samples by one- and two-dimensional lH NMR spectroscopy identifies them as resulting from a true metathesis chain transfer mechanism. These data and the identification of the ring-opened monomer units with alkylidene end groups corresponding to the acyclic chain transfer agent by high resolution mass spectrometry confirm this study as the first example of metathesis of an acyclic olefin by 1. A comparison of the chain transfer activities of a series of acyclic esters yields a reactivity order of terminal olefins > deactivated terminal olefins > internal olefins > deactivated internal olefins, consistent with the behavior of well-characterized homogeneous alkylidene complexes.

Original languageEnglish (US)
Pages (from-to)4742-4747
Number of pages6
JournalMacromolecules
Volume26
Issue number18
DOIs
StatePublished - Jan 1 1993
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

Fingerprint Dive into the research topics of 'Chain Transfer during the Aqueous Ring-Opening Metathesis Polymerization of 7-Oxanorbornene Derivatives'. Together they form a unique fingerprint.

  • Cite this