Metathesis of renewable polyene feedstocks – Indirect evidences of the formation of catalytically active ruthenium allylidene species

Ervin Kovács, Péter Sághy, Gábor Turczel, Imre Tóth, G. Lendvay, Attila Domján, Paul T. Anastas, Róbert Tuba

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Cross-metathesis (CM) of conjugated polyenes, such as 1,6-diphenyl-1,3,5-hexatriene (1) and α-eleostearic acid methyl ester (2) with several olefins, including 1-hexene, dimethyl maleate and cis-stilbene as model compounds has been carried out using (1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)-dichloro(o-isopropoxyphenylmethylene)ruthenium (Hoveyda-Grubbs 2nd generation, HG2) catalyst. The feasibility of these reactions is demonstrated by the observed high conversions and reasonable yields. Thus, regardless of the relatively low electron density, =CH–CH= conjugated units of molecules, including compound 2 as a sustainable, non-foodstuff source, can be utilized as building blocks for the synthesis of various value-added chemicals via olefin metathesis. DFT-studies and the product spectrum of the self-metathesis of 1,6-diphenyl-1,3,5-hexatriene suggest that a Ru η1-allylidene complex is the active species in the reaction.

Original languageEnglish
Pages (from-to)213-217
Number of pages5
JournalJournal of Organometallic Chemistry
Volume847
DOIs
Publication statusPublished - Oct 1 2017

Fingerprint

Diphenylhexatriene
Polyenes
Ruthenium
metathesis
Alkenes
Feedstocks
ruthenium
Olefins
Stilbenes
alkenes
Discrete Fourier transforms
maleates
Carrier concentration
Esters
hexenes
stilbene
Electrons
Catalysts
Molecules
Acids

Keywords

  • Allylidene complexes
  • Green chemistry
  • Metathesis
  • Polyenes
  • Ruthenium

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Metathesis of renewable polyene feedstocks – Indirect evidences of the formation of catalytically active ruthenium allylidene species. / Kovács, Ervin; Sághy, Péter; Turczel, Gábor; Tóth, Imre; Lendvay, G.; Domján, Attila; Anastas, Paul T.; Tuba, Róbert.

In: Journal of Organometallic Chemistry, Vol. 847, 01.10.2017, p. 213-217.

Research output: Contribution to journalArticle

Kovács, Ervin ; Sághy, Péter ; Turczel, Gábor ; Tóth, Imre ; Lendvay, G. ; Domján, Attila ; Anastas, Paul T. ; Tuba, Róbert. / Metathesis of renewable polyene feedstocks – Indirect evidences of the formation of catalytically active ruthenium allylidene species. In: Journal of Organometallic Chemistry. 2017 ; Vol. 847. pp. 213-217.
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