Metathetical cyclization of dienes: tolerance and behavior of a cyclometallated aryloxycarbene complex of tungsten towards diallylic compounds

Michel Leconte, Salvatore Pagano, Andrew Mutch, Frédéric Lefebvre, Jean Marie Basset*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

Intramolecular metathesis of various diallylic compounds containing the O, S, Si or P hetero-elements was achieved in good yields by using the cyclometallated carbene complex W(OAr)(OAr)(CHCMe3)Cl(OEt2). Unsubstituted diallyl ether is converted into 2,5-dihydrofuran; diallyl sulfide is converted into 2,5-dihydrothiophen; diallylphenyl phosphine is converted into 1-phenyl-2,5-dihydro-1H-phosphole; and diallyldimethyl- or diphenylsilanes are converted into the corresponding silacyclopentenes. The metathesis reaction of methyl-substituted diallyl sulfides shows that steric effects are very important. Depending on the position of the methyl groups, the reaction can proceed normally or be completely inhibited.

Original languageEnglish (US)
Pages (from-to)1069-1071
Number of pages3
JournalBulletin de la Societe Chimique de France
Volume132
Issue number10
StatePublished - 1995
Externally publishedYes

Keywords

  • cyclization
  • heteroatom
  • metathesis
  • steric hindrance
  • tungsten

ASJC Scopus subject areas

  • Chemistry(all)

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