The reaction of iminoxy radical with phenols

p-Chlorobenzaldoxime dehydrodimer, which decomposed to iminoxy radicals on heating, reacts with substituted phenols giving acetylamino, t-butylt dimethyl, methoxy and phenyl substituted 2-(4'-chlorophenyl) benzoxazole derivatives. From 1- or 2-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.