Radical polymerization of furan with maleic anhydride through the diels—Alder adduct

Abstract

Equimolar reactions of furan (F), 2-methylfuran (MF), and 2,5-dimethylfuran (DMF) with maleic anhydride in acetone-d6 at 60°C were directly followed by NMR spectra. The rates of formation of the two isomers, endo and exo adducts, formed by the Diels—Alder reactions were in the order: endo form; DMF>F>MF; exo form; DMF> MF>F. The maximum conversions for the endo isomers observed in all cases suggest the isomerization of endo adducts to exo isomers. The polymers formed were not 1: 1 alternating copolymers, but homopolymers resulting from the Diels—Alder adducts of exo form. The complex formed in the reaction system might be the active intermediate for the Diels—Alder reaction, but not for the polymerization reaction.The reaction of furfuryl methacrylate with maleic anhydride provides another example where the Diels—Alder reaction participates in the polymerization reaction . © 1974, The Society of Polymer Science, Japan. All rights reserved.