Oxidation of phenol ortho- and meta-fluoroderivatives with cerium (4) perchlorates

Stoichiometry of oxidation of 2- and 3-fluorophenol, as well as 2,3- and 2,6-difluorophenol by cerium (4) perchlorate in HClO4 aqueous solutions has been determined. Processes of oxidation of high-molecular condensation products are the stages limiting the rate of the reactions in case of 2-, 3-fluorophenol and 2,3-difluorophenol; stages of oxidation of 4,4'-diphenoquinone and n-benzoquinone fluoroderivatives play the role for 2,6-difluorophenol and 2-fluorophenol. Oxidation rate of 2,6-difluorophenol is also limited by the oxidation stage of 4-phenoxyphenol fluoroderivative. On the basis of experimental data and quantum-mechanical calculations the mechanisms of the processes studied are suggested