Poly(alkylene oxide) ionomers VIII. Synthesis of methyl ω‐alkenoates and methyl ω‐epoxyalkanoates

Abstract ω‐Alkenoic acids, either commercially available or synthesized, were esterified to their corresponding methyl esters. They were characterized by their infrared, 1 H‐, and 13 C‐NMR spectra. The ω‐alkenoates prepared were: propenoate (acrylic acid), butenoate, pentenoate, hexenoate, heptenoate, octenoate, nonenoate, and decenoate. These compounds were epoxidized with m ‐chloroperoxybenzoic acid to the corresponding methyl ω‐epoxyalkanoates. The rate of epoxidation of the double bond is found to increase as the double bond is separated from the carbomethoxy group by increasing numbers of methylene groups. When at least three methylene groups are inserted, the rate of epoxidation becomes constant and is similar to the epoxidation of ω‐olefins. The methyl ω‐epoxyalkanoates were characterized by their infrared, 1 H‐, and 13 C‐NMR spectra. Methyl ω‐alkenoates and methyl ω‐epoxyalkanoates were prepared and characterized, and their purification was studied in preparation for their investigation as monomers for olefin or epoxide polymerization using corrdination initiators.