Friedel-Crafts Reactions of Phenols with Cyanuric Chloride

HORIKOSHI Yoshio, OHTO Yukio, SEKIGUCHI Shizen, MATSUI Kohji

doi:10.1246/nikkashi.1974.530

Reactions of phenols with Cyanuric chloride in the presence of aluminium chloride were carried out in e-dichlorobenzene and benzene. ln the reactionof p-chlorophenol with cyanuric chloride in a molar ratio of 3:1, only tris(P-chlorophenoxy)-s-triazine was obtained as a result of O-s-triazinylation ef chlorophenol, whi1e in the case of P-cresol, 2-(5-methyl-2-hydroxyphenyl)-4, 6-bis(P-tolyloxy)-s-triazine and 2, 4-bis(5-methyl-2-hydroxyphenyl)-6-(P-telyloxy)-s--triazine were obtained as the C-s-triazinylation preducts in addition to tris(p-tolyloxy)-striazine. ln the cases of m-cresol, resorcinol, ev-and B-naphthel, however, all the reaction products wereoftype, showing that the l course of these reactions depended mainly upon the reactivites of phenols towards electrophiles; theO-condensation predominated when phenol of low reactivity was used, while the C--condensation predominated when phenol of high reactivity was employed, and boththe O- and C-condensations occurred in the case of phenol of medium reactivity sueh as P-cresol. ln the cases of m-cresol, resorcinol and B-naphthol, the C-condensation took place at the ortho position of hydroxy group and condensation products centaining two or three phenol nuclei in one s-triazine ring were obtained, even when the reactions with cyanuric chloride were carried out in a mo!ar ratioof1:1. ln these cases it is suggested that the phenols reacted preferentially withprimary and/or secondary condensation products whese residual chlorine atoms areassumed to be more reactive than those of cyanuric chloride by the presence of achelate ring in the aluminium chloride eomplexes.

Friedel-Crafts Reactions of Phenols with Cyanuric Chloride

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