Abstract
Attempts were made to copolymerize p‐aminostyrene, p‐acetamidostyrene, N‐methyl‐p‐aceta‐midostyrene, N‐(4‐vinylphenyl) phthalimide, N‐vinyl succinimide, and N‐vinyl phthalimide with methyl acrylate complexed with ethyl aluminum sesquichloride. Only reactions involving N‐(4‐vinylphenyl)phthalimide and N‐vinyl phthalimide yielded alternating copolymers. N‐vinyl succinimide gave nonalternating copolymers insoluble in common solvents and the other monomers did not copolymerize. In some cases, the conventional radical copolymers were prepared for comparison purposes. The reactivity ratios of the free‐radical initiated copolymerization of methyl acrylate (I) with N‐(4‐vinylphenyl)phthalimide (II) were r~1~ = 0.14 and r~2~ 1.56. The alternating copolymers were studied by ^1^H‐NMR and ^13^C‐NMR spectroscopy. The alternating copolymer of N‐(4‐vinylphenyl)phthalimide with methyl acrylate was hydrazinolyzed to form the alternating copolymer of methyl acrylate with p‐aminostyrene. Hydrazinolysis of the alternating copolymer of methyl acrylate with N‐vinyl phthalimide removed the phthalimide moiety and generated vinyl amine units which readily cyclized with neighboring methyl acrylate units to form copolymers that contained five‐membered lactam rings. The infrared (IR) spectra of the hydrazinolyzed products contain bands due to amine or amide groups and are devoid of the characteristic bands of the phthalimide ring.