Synthesis and Polymerization of N-Arylitaconimides: Free Radically and Anionic ally

N-Phenyl-, N-p-tolyl-, N-p-methoxyphenyl, N-o-ethyl phenyl-, and N-p-chlorophenylitaconimides were prepared from the corresponding taxonomic acids. These monomers were polymerized free radically to yield low molecular weight polymers. With the exception of N-p-chlorophenylitaconimide, all the above monomers polymerized anionic ally using n-butyl lithium as initiator. N-o-Ethylphenylitaconimide formed a cross-linked polymer when polymerized anionic ally. The inability of N-arylitaconimides to produce high molecular weight polymers was attributed to the allelic hydrogen's of the monomers.