Impact of electronic modification of the chelating benzylidene ligand in cis-dichloro-configured second-generation olefin metathesis catalysts on their activity

Eva Pump, Albert Poater, Michaela Zirngast, Ana Torvisco, Roland C. Fischer, Luigi Cavallo, Christian Slugovc

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

A series of electronically modified second-generation cis-dichloro ruthenium ester chelating benzylidene complexes was prepared, characterized, and benchmarked in a typical ring-opening metathesis polymerization (ROMP) experiment. The electronic tuning of the parent chelating benzylidene ligand (2-ethyl ester benzylidene) was achieved by substitution at the 4- and 5-positions with electron-withdrawing nitro or electron-donating methoxy groups. The effect of the electronic tuning on the cis-trans isomerization process was studied experimentally and theoretically. Density functional theory calculations clearly revealed the influence of electronic modification on the relative stability between the cis and trans isomers, which is decisive for the activity of the studied compounds as initiators in ROMP. © 2014 American Chemical Society.
Original languageEnglish (US)
Pages (from-to)2806-2813
Number of pages8
JournalOrganometallics
Volume33
Issue number11
DOIs
StatePublished - May 27 2014

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

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