Mechanistic Insights into Polar Monomer Insertion Polymerization from Acrylamides
作者： Tobias Friedberger , Philipp Wucher , Stefan Mecking
DOI: 10.1021/JA207110U
关键词: Ethyl acetate 、 Acrylate 、 Chemistry 、 Acetonitrile 、 Ethylene 、 Monomer 、 Polymer chemistry 、 Polymerization 、 Amide 、 Methyl acrylate
摘要: N-Isopropyl acrylamide (NIPAM), N,N-dimethyl (DMAA), and 2-acetamidoethyl acrylate (AcAMEA) were copolymerized with ethylene employing [(P^O)PdMe(DMSO)] (1-DMSO; P^O = κ2-P,O-Ar2PC6H4SO2O Ar 2-MeOC6H4) as a catalyst precursor. Inhibition studies nonpolymerizable polar additives show that reversible κ-O-coordination of free amide retards polymerization significantly. Retardation increases in the order ethyl acetate ≪ methyl sulfone < acetonitrile N,N-dimethylacetamide ≈ N-methylacetamide propionic acid dimethylsulfoxide. Pseudo-first-order rate constants for insertion into 1-DMSO determined to increase DMAA AcAMEA NIPAM acrylate. Exposure resulted formation consecutive products [(P^O)Pd(C6H11NO2)nMe] (n ≤ 3), by electrospray ionization mass spectrometry. The solid-state structure methanol adduct 2,1-insertion product 1-DMSO, [(P^O)Pd{η1-CH(...
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