Abstract: p-Chlorobenzaldoxime dehydrodimer, which decomposed to iminoxy radicals on heating, reacts with substituted phenols giving acetylamino, t-butyl, dimethyl, methoxy and phenyl substituted 2-(4'-chlorophenyl)benzoxazole derivatives. From 1-or2-naphthol, 8-hydroxyquinoline and bisphenol A,2-(4'-chlorophenyl)naphth[2,1-d]oxazole(6), 2-(4'-chlorophenyl)naphth[1,2-d]oxazole(5), 2-(4'-chlorophenyl)oxazolo[4,5-h]quinoline(7) and 2,2-bis[5'-(2'-(4"-chlorophenyl)benzoxazolyl)]-propane(8) were obtained. This is a new kind of radical substitution reaction. And a mechanism of the reaction is proposed.

Key words: Iminoxy radical, Radical substitution reaction, Benzoxazole