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.
- Diallyl compounds
- Functional olefins
- Olefin metathesis
- Steric crowding
ASJC Scopus subject areas
- Process Chemistry and Technology
- Physical and Theoretical Chemistry