N. Maeno, T. Itagaki, S. Uno
Oct 1, 1972
Citations
0
Influential Citations
5
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Several 4- or 5-substituted O-(s-triazinyl)-2-aminophenols were synthesized, and the kinetics of the Smiles rearrangement of these compounds have been studied spectrophotometrically in methanol, ethanol, and 2-propanol in order to make clear the effects of substituents on the rearrangement. Substituents in the s-triazine nucleus were found to affect the progress of the reaction to a great extent by changing the positive character of the triazine-ring carbon. On the other hand, a substituent in the aminophenol moiety affects both the nucleophilic reactivity of the attacking amino group and the stability of the leaving phenoxide anion or the reactivity of the s-triazinyl group, but the effect on the amino group was found to be predominant, the effect of a substituent in the aminophenol moiety was smaller than that of the substituents in the s-triazine nucleus.