MICROPEROXIDASE H2O2-MEDIATED ALKOXYLATING DEHALOGENATION OF HALOPHENOL DERIVATIVES IN ALCOHOLIC MEDIA/

The results of this study report the H2O2 driven microperoxidase-8 (MP S)-catalyzed dehalogenation of halophenols such as 4-fluorophenol, 4-c hlorophenol, 4-bromophenol, and 2-fluorophenol in alcoholic solvents, In methanol, the conversion of the para-halophenols and 2-fluorophenol to, respectively, 4-methoxyphenol and 2-methoxyphenol, as the major d ehalogenated products is observed, In ethanol, 4-ethoxyphenol is the p rincipal dehalogenated product formed from 4-fluorophenol. Two mechani sms are suggested for this MP8-dependent alkoxylating dehalogenation r eaction, In one of these mechanisms the oxene resonant form of compoun d I of MP8 is suggested to react with methanol forming a cofactor-pero xide-alkyl intermediate. This intermediate reacts with the reactive pi -electrons of the substrate, leading to the formation of the alkoxyphe nols and the release of the fluorine substituent as fluoride anion.