Polymerization of vinylbenzamides

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Abstract
In the base‐catalyzed polymerization of p‐vinylbenzamide, hydrogen‐transfer polymerization occurs. The structure of the new polymer was identified. Various effects on the hydrogen‐transfer polymerization of p‐vinylbenzamide were studied. The infrared spectrum of the oligomer has characteristic absorptions of secondary amide, as well as weak absorption of the vinyl group. The oligomer also gives a hydrogen‐migrated polymer with anionic catalysts. From these facts a possible polymerization mechanism was proposed. The hydrogen‐transfer polymerization occurred most readily with the p‐vinylbenzamide, next and to a small extent with the meta‐substituted isomer, and hardly with the o‐substituted isomer. o‐Vinylbenzamide gives 3,4‐dihydroisocarbostyril.