Soluble Polymer-Supported Catalysts Containing Pendant Quaternary Onium Salt Residues for Regioselective Addition Reaction of Epoxy Compound with Active Ester

Abstract

Various soluble polymer-supported catalysts containing pendant quaternary onium salts were synthesised by the radical copolymerisation of p-chloromethylated styrene with styrene followed by the addition reaction of the resulting copolymers with tributylamine or trialkylphosphines. The catalytic activity of the soluble polymer-supported quaternary onium salts on the regioselective addition reaction of phenyl glycidyl ether (PIE) with S-phenyl thioacetate (PTA) was evaluated from the rates of the reaction and yields of the product, 1-phenoxy-3-(phenylthio)-2-propyl acetate (PPA). The catalytic activity was strongly affected by the content ofpendant quaternary onium salt in the polymer chains, by the structure of onium salt residues, and by the reaction solvents used