Polymeric catalysis: Imidazoles grafted onto poly(vinylamine). I. Synthesis and grafting of imidazolylalkanoic acids

Abstract

Some Ω-(1-imidazolyl) and Ω-[4(5)-imidazolyl]alkanoic acids were synthesized and grafted onto poly(vinylamine) with an amide bond. These water-soluble grafts were used to study the kinetics of the esterolysis of activated phenyl esters. The 1-substituted imidazoles were prepared by the reaction of the sodium salt of imidazole with the ethyl Ω-bromoalkanoates. The 4(5)-substituted imidazoles were prepared from urocanic acid or 4(5)-hydroxymethylimidazole. The Ω-(1-imidazolyl)alkanoic acids were grafted onto poly(vinylamine) via their acyl–guanidine derivatives; the 3-[4(5)-imidazolyl]propanoic acid was grafted with a water-soluble carbodiimide.