Searching for the hidden hydrides: the competition between alkene isomerization and metathesis with Grubbs catalysts

Ian W. Ashworth, Ian H. Hillier, David J Nelson, Jonathan M Percy, Mark A. Vincent

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Although Grubbs metathesis catalysts have enabled syntheses of a range of molecules, alkene isomerization, a known and problematic side reaction, is poorly understood. Several mechanisms which have been advanced to account for isomerization were studied by using electronic structure calculations. The pathway catalyzed by a ruthenium hydride emerged as the most facile process by a significant margin. For the first time, we have obtained experimental evidence for the presence of this species in a metathesis-active system.

LanguageEnglish
Pages5673–5677
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2012
Issue number29
DOIs
Publication statusPublished - Oct 2012

Fingerprint

metathesis
Alkenes
Isomerization
Hydrides
isomerization
alkenes
hydrides
catalysts
Catalysts
Ruthenium
ruthenium
Electronic structure
margins
electronic structure
Molecules
synthesis
molecules

Keywords

  • ruthenium
  • metathesis
  • homogeneous catalysis
  • density functional calculations
  • kinetics

Cite this

Ashworth, Ian W. ; Hillier, Ian H. ; Nelson, David J ; Percy, Jonathan M ; Vincent, Mark A. / Searching for the hidden hydrides : the competition between alkene isomerization and metathesis with Grubbs catalysts. In: European Journal of Organic Chemistry. 2012 ; Vol. 2012, No. 29. pp. 5673–5677.
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Searching for the hidden hydrides : the competition between alkene isomerization and metathesis with Grubbs catalysts. / Ashworth, Ian W.; Hillier, Ian H.; Nelson, David J; Percy, Jonathan M; Vincent, Mark A.

In: European Journal of Organic Chemistry, Vol. 2012, No. 29, 10.2012, p. 5673–5677.

Research output: Contribution to journalArticle

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