リッター反応によるアクリルアミド誘導体の合成

抄録

This paper describes the results obtained in applying the Ritter reaction to syntheses of N-substituted acrylamides. N- [1- (p-chlorophenyl) ethyl] acrylamide (1a), N- [1- (p-chlorophenyl) isopropyl] acrylamide (1c) and N-[1- (p-chlorophenyl) -1-methylpropyl] acrylamide (1d) were prepared by the reaction of acrylonitrile and each one of p-chlorophenylmethylcarbinol, p-chloro-α, α-dimethylbenzyl alcohol and 2- (p-chlorophenyl) -2-butanol in the presence of concentrated sulfuric acid.
Similarly, N- [1- (p-chlorophenyl) ethyl] methacrylamide (1b) was prepared from methacrylonitrile.
When the reaction was carried out with N- (hydroxymethyl) -p-toluamide, N- (hydroxymethyl) -p-chlorobenzamide and N- (hydroxymethyl) -2-naphthamide, three methylene-bis-amides, i. e., N- (p-toluamidomethyl) acrylamide (3e), N- (p-chlorobenzamidomethyl) acrylamide (3f) and N- (2-naphthamidomethyl) acrylamide (3h) were obtained.
Reaction of N- (hydroxymethyl) acrylamide with benzonitrile or with methacrylonitrile could be achieved, and N-benzamidornethyiacrylamide (5) or N-acrylamidomethylmethacrylamide (6) was prepared.
Benzoyl peroxide catalyzed polymerization of (1a), (1b), (1c) and (1d) gave vinyl polymers.
Vinyl polymerization of (3e), (3f), (3h) and (5) were also investigated by potassium persulfate catalyst.
It was recognized that sodium tert-butoxide catalyzed polymer of (1a), (1d), (3f), (3h) and (5) were hydrogen migrated polymer at least predominantly.