The addition of partially dehydroxylated silica (PDS) to a solution of the Wilkinson WMe6 as well as the Schrock W neopentylidyne tris neopentyl complex catalyzes linear or cyclic alkanes to produce respectively a distribution of linear alkanes from methane up to triacontane or a mixture of cyclic and macrocyclic hydrocarbons. This single catalytic system transforms also linear α-olefins into higher and lower homologues via an isomerization/metathesis mechanism (ISOMET). This complex is also efficient towards functionalized olefins. Unsaturated fatty acid esters (FAEs) are converted into diesters corresponding to self-metathesis products.
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Graphical abstract
HighlightsMetathesis of unsaturated fatty acid esters (FAEs) by W-based single catalytic system resulted only on the primary self-metathesis products (diesters). The selectivity of this transformation via multifunctional catalyst, which previously found to be active in isomerization and metathesis (ISOMET) of unfunctionalized α-olefins is studied.
ABSTRACTMetathesis of unsaturated fatty acid esters (FAEs) by silica supported multifunctional W-based catalyst is disclosed. This transformation represents a novel route towards unsaturated di-esters. Especially, the self-metathesis of ethyl undecylenate results almost exclusively on the homo-coupling product whereas with such catalyst, 1-decene gives ISOMET (isomerization and metathesis olefin) products. The olefin metathesis in the presence of esters is very selective without any secondary cross-metathesis products demonstrating that a high selective olefin metathesis could operate at 150 . Additionally, a cross-metathesis of unsaturated FAEs and α-olefins allowed the synthesis of the corresponding ester with longer hydrocarbon skeleton without isomerisation.
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