Abstract
The oxidative coupling polymerization of p alkoxyphenols with Mn(acac)2ethylenediamine catalysts was carried out. The polymerization of pmethoxyphenol with the manganese(II) acetylacetonate [Mn(acac)2]N,N’diethylethylene diamine catalyst in CH2Cl2 at room temperature under an O2 atmosphere afforded a polymer, which mainly consists of the mphenylene unit, whereas the polymer obtained with Mn(acac)2 was rich in the oxyphenylene structure. The polymer yield and regioselectivity were significantly affected by the monomer and catalyst structures. The former catalyst system was also used for the coupling reaction of 2methoxy 4methylphenol. The corresponding carboncar bon coupling product was isolated with a regioselectivity of 95%.
Highlights
Phenolic polymers bearing a polyphenylene main chain structure have been mainly synthesized by the transition-metal-catalyzed coupling reactions of aryl halides, such as the Wurtz coupling, Ullmann reaction, Kumada-Tamao-Corriu coupling, etc [1,2,3,4]
The catalytic oxidative coupling polymerization (OCP) of 2,6-dimethylphenol is industrially utilized for the synthesis of poly(2,6-dimethyl-1,4phenylene ether) (PPE), which is one of the most common engineering plastics [5,6,7]
We reported that the OCP of the bifunctional p-alkoxyphenol monomer 2 (Scheme 2) using the commercially available and typical copper catalyst, di- -hydroxo-bis[(N,N,N’,N’tetramethylethylenediamine)copper(II)] chloride [CuCl (OH)-TMEDA] proceeds in a regioselective manner to afford a polymer with a CC-unit selectivity of up to 88% [17]
Summary
Phenolic polymers bearing a polyphenylene main chain structure have been mainly synthesized by the transition-metal-catalyzed coupling reactions of aryl halides, such as the Wurtz coupling, Ullmann reaction, Kumada-Tamao-Corriu coupling, etc [1,2,3,4]. These reactions are suitable for the regio and/or coupling selective formation of carbon-carbon bonds between aromatics. We reported that the OCP of the bifunctional p-alkoxyphenol monomer 2 (Scheme 2) using the commercially available and typical copper catalyst, di- -hydroxo-bis[(N,N,N’,N’tetramethylethylenediamine)copper(II)] chloride [CuCl (OH)-TMEDA] proceeds in a regioselective manner to afford a polymer with a CC-unit selectivity of up to 88% [17]. The OCP of the p-alkoxyphenols 1 with various metal catalysts was investigated, and novel manganese (II) acetylacetonate [Mn(acac)2]-ethylenediamine catalysts for the CC-selective coupling formation were found
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