Copolymerization of 1-Decene with Alkyl and Alkenyl Methacrylates Catalyzed by Palladium–diimine Complexes

Abstract

Palladium–diimine complexes catalyzed copolymerization of 1-decene with methyl methacrylate (MMA) to produce polymer with vinylene groups in the polymer chain, and a methyl methacrylate group, –CH₂–CH(Me)–COOMe, at the polymer end. Previous findings of copolymerization catalyzed by Ni complexes with chelating P–O ligands gave a polymer with an unsaturated end group, –CH = C(Me)COOMe. Other alkyl methacrylates such as n-butyl, t-butyl, and i-amyl methacrylates also copolymerized with 1-decene to yield the end-functionalized polymers. Copolymerization of 1-decene with 2-acetylethyl methacrylate yielded polymer with a terminal ester group, whereas 2-hydroxyethyl methacrylate did not undergo copolymerization. Allyl methacrylate reacted with 1-decene to produce copolymer via preferential insertion of C = C double bond of the allyl groups into the metal-polymer bond. Copolymer of 1-decene and isoprenyl methacrylate contained comonomer units formed via insertion of C = C double bonds of the methacrylic group and of isoprenyl group in 76 : 24 ratio.