Ozonization of phenothiazine and its analogues

Article abstract of DOI:10.1246/bcsj.57.2526

When phenothiazine and phenoxazine were ozonized in dichloromethane, the cation radicals and the ozonate anion radicals were detected, whereas, in the ozonization of phenoxathiin and thianthrene, these radicals were not observed. Formation of these radicals was more favorable as greater was the polarity of the solvent and lower was the oxidation potential of the substrate. Ozonization of phenothiazine and phenoxazine in polar solvents was explained by the electron-transfer mechanism accompanied by the electrophilic ozone attack, and that of phenoxathiin and thianthrene by the electrophilic ozone attack alone.