In the Friedel-Crafts reaction of xylenes with either cyanuric chloride or 2, 4-dichloro-6-methoxy-S-triazine (DCMT), the differences in reactivity with xylene isomers and their condensed products were investigated. The initial rates of the reaction with cyanuric chloride were determined to be (-dx/dt)t=o=85, 182 and 30 (mol%)(hr
-1) for o-, m-, and p-xylene, respectively. When DCMT was used, the reactivity again decreased in the following order ; m->o->p-xylene. 2, 4, 6-Tris(2', 5'-dimethylphenyl)-s-triazine (mp 112-113.5°C) was obtained from p-xylene and cyanuric chloride in a yield of 6.9%. Upon treatment with DCMT, o- or m-xylene gave 2, 4-his (dimethylphenyl)-s-triazine-6-(1H)-onecorresponding to the original xylene in a yield of 12%. Similar reaction using p-xylene, however, was very difficult.
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