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Ring Opening Metathesis Polymerization of 7-Oxabicyclo[2.2.1]Hept-5-Ene-2,3- Dicarboxylic Acid, Dimethyl Ester
Published: 03 November 2014 by MDPI in The 18th International Electronic Conference on Synthetic Organic Chemistry session Polymer and Supramolecular Chemistry
Abstract: All the monomers used in ring opening metathesis polymerization ( ROMP) were synthesized by two step reactions. The first step of the synthesis was the Diels-Alder reaction between furan and maleic anhydride to produce exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride. The second step was to prepared 7-oxabicyclo[2.2.1]hept-5-ene-2,3- dicarboxylic acid, dimethyl ester by Fischer estrification of exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride in refluxing methanol.7-Oxabicyclo[2.2.1]hept-5-ene-2,3- dicarboxylic acid, dimethyl ester was polymerized by ROMP catalyzed by commercially available ruthenium catalyst Ru(PPh3)2(Cl)2(CHPh) at defined concentrations relative to the monomer. Depending on the molar ratio of the monomer to the catalyst polymers with different large molecular weight were obtained. Molecular weights and polydispersities were confirmed by gel permeation chromatography. Monomers and polymers were also analyzed by FT-IR.Polyanions of poly (7-oxanorbornene-2,3-dicarboxylate) were prepared by hydrolysis of poly (dimethyl-7-oxabicyclo (2.2.1) hept-5-ene-2,3-dicarboxylic acid).It is worth noting that the polyanions in aqueous solution form a gel, were lubricious.The properities of the prepared polymers will be discussed in full paper.
Keywords: Ring Opening Metathesis Polymerization; 7- oxanorbornene derivatives; polyanion