γ-Radiation-Initiated Formation of Phenol and Diphenyl Ether from Halobenzenes

The formation of phenol was observed in aqueous alkaline solutions of chlorobenzene. Diphenyl ether was formed in aqueous tert-butanol solutions of chlorobenzene and bromobenzene in the presence of phenoxide ions. An increase in the temperature of irradiation resulted in an increase in the yields of phenol and diphenyl ether. At a temperature higher than 150°C, chain reactions of phenol and diphenyl ether formation occurred. It is likely that the dissociation of halobenzene radical anions is the rate-limiting step of the processes.