Comparison of Reactivity in the Cross Metathesis of Allyl Acetate‐Derivatives with Oleochemical Compounds

Abstract

The metathesis of unsaturated oleochemicals is an excellent tool for generating α,ω‐difunctional substrates, which are useful intermediates for polymer synthesis. This article describes the cross metathesis of allyl acetate and cis‐1,4‐diacetoxy‐2‐butene with methyl 10‐undecenoate and methyl oleate, which are oleochemical key substrates. Detailed optimizations led to high conversion rates and yields of the desired products under mild reaction conditions by using a low concentration of commercially available homogeneous ruthenium catalysts.

Fatty Acids and their Derivatives as Renewable Platform Molecules for the Chemical Industry

“…[106] 3.2.6.2. Cross-Metathesis with Functionalized Alkenes Cross-metathesis of unsaturated fatty compounds with functionalized alkenes,s uch as methyl acrylate, [107] dimethyl maleate, [108] maleic acid, [109] allyl acetate and cis-1,4-diacetoxy-2-butene, [110][111][112] acrylonitrile, [113,114] or acrolein [115] gives straightforward access to interesting bifunctional unsaturated compounds with typically high (E)-stereoselectivity.…”

Fettsäuren und Fettsäurederivate als nachwachsende Plattformmoleküle für die chemische Industrie

“…[106] 3.2.6.2. Kreuz-Metathese mit funktionalisierten Alkenen Die Kreuz-Metathese von ungesättigten Fettstoffen mit funktionalisierten Alkenen, wie Methylacrylat, [107] Dimethylmaleat" [108] Maleinsäure, [109] Allylacetat und cis-1,4-Diacetoxy-2-buten, [110][111][112] Acrylnitril [113,114] oder Acrolein, [115] ermçglicht den einfachen und oft mit hoher (E)-Stereoselektivitätv erbundenem Zugang zu interessanten bifunktionellen ungesättigten Verbindungen.…”

Ethenolysis: A Green Catalytic Tool to Cleave Carbon–Carbon Double Bonds

“…Among them, the sequence involving several olefin metathesis transformations can be highlighted. Self‐metathesis produces diesters and cross‐metathesis with a variety electron‐deficient alkenes, such as acrylates and equivalents, acrolein, acrylonitrile, allyl chloride, allyl acetate, but‐3‐enenitrile, or pent‐4‐enenitrile, provides useful α,ω‐bifunctional polymer precursors (Scheme ). Metathesis not only with double bonds but also with triple bonds makes possible a straightforward access to long‐chain conjugated dienes that cannot be produced from internal linear olefins …”