二, 三のエチレンヂアミン型化合物の究極メチル化に就て

抄録

Hoffmann's exhaustive methylation was carried out on N-(β-dimethylaminoethyl)-α-pyridone (I), -α-quinnolone (II), -phthalimidine (III), -α-piperidone (IV), -α-pyrrolidone (V), phenylacetic acid-(β-dimethylaminoethylmethylamide) (VI), -(β-dimethylaminoethylamide) (VII) and benzoie acid-(β-dimethylaminoethylamide) (VIII). It was found that compounds in which the H-atom attached to C-atom in β-position is easily liberated as a proton undergo olefin decomposition to give N-vinyl compounds, as in (I) and (II) where N-vinyl-α-pyridone and -α-quinolone, respectively, are formed. Other compounds such as (IV), (V) and (VI) undergo alcoholic decomposition. (III) is an intermediate of these two, while (VII) and (VIII) give some products which are assumed to be due to N-vinyl compound formed by olefin decomposition. The ease or difficulty in liberation of H at β-C as a proton depends on the effect of the lactam ring or acid amide radical, becoming easier as these tend to negative effect. The author has made some explanations of these decomposition reactions from electronic theory.