A new route to functional polymers: Synthesis of functional polymer-supported esters from a weak acid ion exchange resin

Treatment of Amberlite IRC-50, a weak acid cation exchange resin containing methacrylic acid residues, with tetra-n-butylammonium hydroxide or benzyltrimethylammonium hydroxide gives the corresponding polymer-supported quaternary ammonium salts. These react smoothly, in nucleophilic substitution reactions, with a range of alkyl halides or sulfonates to give side chain esters with saturated hydrocarbon groups, with quaternary ammonium or sulfonate salt groups, with halide or alcohol groups at the terminus of spacer chains, with 1,2-diol groups, with acetylenic groups or with anthracene residues. These polymer-supported species have a variety of potential applications.