Phenolic oxidation of o,o '-dihalogenated phenols

A detailed inspection of phenolic oxidation products derived from the o,o'- dihalogenated cresol derivatives (1a - 1e) indicated that the bromo and chl oro substituents promoted the oxidation leading to the corresponding diaryl ethers, whereas the iodo derivatives provided the diaryls. Selective reduc tion of 6d and its tyrosine derivative afforded the corresponding diaryl et hers carrying two chlorine atoms (14, 15). interpretation of the selectivit y of the phenolic oxidation was attempted by employing theoretical calculat ions. (C) 1999 Elsevier Science Ltd. All rights reserved.