Phenolic oxidation of o,o'-dihalogenated phenols

Article abstract of DOI:10.1016/S0040-4020(99)00217-3

A detailed inspection of phenolic oxidation products derived from the o,o'-dihalogenated cresol derivatives (1a - 1e) indicated that the bromo and chloro substituents promoted the oxidation leading to the corresponding diaryl ethers, whereas the iodo derivatives provided the diaryls. Selective reduction of 6d and its tyrosine derivative afforded the corresponding diaryl ethers carrying two chlorine atoms (14, 15). Interpretation of the selectivity of the phenolic oxidation was attempted by employing theoretical calculations.