Metathetical cyclization of dienes containing P, O, S or Si heteroatoms by a cyclometallated aryloxy-carbene of tungsten. Inhibition effects and steric constraints: A review

Salvatore Pagano, Andrew Mutch, Frédéric Lefebvre*, Jean-Marie Maurice Basset

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Intramolecular metathesis of various diallyl compounds containing the O, S, Si or P hetero element was achieved with good yields by using the cyclometallated carbene complex W(OAr) (OAr)(CHMe3)Cl(OEt2). Unsubstituted diallyl ether is converted into 2,5-dihydrofuran; diallyl sulfide is converted into 2,5-dihydrothiophen; diallyl-phenyl phosphine is converted into phenyl-2,5-phospholen and diallyl dimethyl- or diphenylsilanes are converted into the corresponding silacyclopentenes. Metathesis reaction of methyl-substituted diallyl-sulfides shows that steric effects are very important. These steric effects are also well seen by addition of di-n-propyl or di-i-propyl sulfides during the metathesis reaction of diallyl sulfide. Indeed, only the former compound inhibit the reaction, showing that there is an important steric crowding around the tungsten atom.

Original languageEnglish (US)
Pages (from-to)61-65
Number of pages5
JournalJournal of Molecular Catalysis A: Chemical
Volume133
Issue number1-2
DOIs
StatePublished - Jul 13 1998

Keywords

  • Diallyl compounds
  • Functional olefins
  • Olefin metathesis
  • Steric crowding

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology
  • Physical and Theoretical Chemistry

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