Synthesis of poly(diethyl 2-acetamido-2-vinylbenzyl-malonate). Potential precursor for poly(vinylphenylalanine)

Abstract

Recently, the direct 'step growth' polymerization of protected amino acids or dipeptide 'monomers' was carried out. These polymerization reactions involved functional groups located at the amino acid side chains. However, we have initiated a program wherein the side groups in amino acids have been modified with a vinyl group. The vinyl substituted amino acids can then be polymerized via addition type polymerizations. This paper presents our investigations into the synthesis and polymerization of diethyl 2-acetamido-2-vinylbenzyl-malonate and its attempted hydrolysis to obtain polymers with pendant free amino acids. An attempt has also been made to alkylate poly(chloromethylsytrene) with diethyl 2-acetamido malonate using a phase transfer catalyst (PTC).