Reactions of 3,5-Dimethylbenzene-1,4-diazoöxide

When 3,5-dimethylbenzene-1,4-diazoöxide was heated or irradiated with ultraviolet light in chlorinated hydrocarbons, the corresponding diazonium salt was obtained. When heated in chlorobenzene, the diazoöxide formed a mixture of hydroxybiphenyls and the diazonium salt. These results suggest the formation of an intermediate with free radical character. With boron trifluoride, a hydrated complex was obtained. The decomposition of the diazoöxide in tetrahydrofuran, thermally or photochemically, gave a one-to-one copolymer with the solvent. The product was crystalline under certain conditions. A cationic mechanism for this copolymerization is suggested.