Yoji Hashida

The reactions of 2-substituted 4-chloro-6-(2-hydroxy-1-naphthyl)-1,3,5-triazines with several nucleophiles.

The nucleophilic substitution reactions of 2-methoxy- and 2-diethylamino-4-chloro-6-(2-hydroxy-1-naphthyl)-1,3,5-triazines (1) with aniline, diethylamine, sodium azide, and sodium methoxide were carried out and compared with the reactions of the corresponding derivatives of 4-chloro-6-(4-hydroxy-1-naphthyl)-1,3,5-triazine (2) and 4-chloro-6-(1-naphthyl)-1,3,5-triazine (3). Compound 1 was found to be more reactive than the corresponding (2) and (3), not only in the reactions of a neutral molecule, but also in those of anionic species. The results of the reactions of neutral species are interpreted in terms of the difference in solvation toward the substrates; however, the loss of coplanarity between the naphthalene and triazine nuclei may be responsible for the high reactivity of Compound 1 in the reactions of anionic species.