フェナントレン誘導体の研究 (第5報)
Perkin-Oglialoro反応成績体の幾何異性について その1
1962 年 82 巻 8 号 p. 1115-1120
詳細
1962 年 82 巻 8 号 p. 1115-1120
The Perkin-Oglialoro reaction was carried out on phenylacetic acid, 2-nitro-4, 5-methylenedioxybenzaldehyde, and 2-nitro-4, 5-dimethoxybenzaldehyde and α-phenyl-2-nitromethylenedioxycinnamic acid (I and II) and α-phenyl-2-nitro-4, 5-dimethoxy-cinnamic acid (V and VI) were obtained, by which the presence of hitherto unknown stereoisomers was clarified.
The effect of Perkin-Oglialoro reaction on the formation of stereoisomers under various conditions was examined and the formation ratio was found to be affected approximately by the following conditions:
1) Formation ratio of the trans type increased when inorganic salt of phenylacetic acids was used.
2) Formation ratio of the cis type increased by the use of an organic base as the condensation agent rather than inorganic salt of phenylacetic acids.
3) Under the use of a same agent, the higher reaction temperature resulted in higher formation of the cis type and the lower temperature increased the formation of the trans type.
The ultraviolet absorption spectra of the stereoisomers were compared.
