Hydrogen migration polymerization of N‐substituted acrylamides

The modes of polymerization of N‐substituted acrylamides catalyzed by sodium tert‐butoxide at 105°C. were investigated by means of IR spectra. N‐cyclohexylacrylamide gave a vinyl polymer. All other monomers (N‐substituents were benzyl, p‐phenethyl, p‐anisyl, p‐tolyl, phenyl, and m‐chlorophenyl) gave hydrogen‐migrated polymers, i.e., poly‐N‐substituted‐β‐alanines. Thus electron‐releasing or ‐attracting effects of the N‐substituents, i.e., acidities of migrating amide‐hydrogens, might be responsible for the choice of type of polymerization.