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Microperoxidase/H2O2-mediated Alkoxylating Dehalogenation of Halophenol Derivatives in Alcoholic Media

Microperoxidase/H2O2-mediated Alkoxylating Dehalogenation of Halophenol Derivatives in Alcoholic Media

A M Osman, S Boeren, M G Boersma, C Veeger, I M Rietjens

Proc Natl Acad Sci U S A. 1997 Apr 29;94(9):4295-9.

PMID: 9113983

Abstract:

The results of this study report the H2O2-driven microperoxidase-8 (MP8)-catalyzed dehalogenation of halophenols such as 4-fluorophenol, 4-chlorophenol, 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 dehalogenated products is observed. In ethanol, 4-ethoxyphenol is the principal dehalogenated product formed from 4-fluorophenol. Two mechanisms are suggested for this MP8-dependent alkoxylating dehalogenation reaction. In one of these mechanisms the oxene resonant form of compound I of MP8 is suggested to react with methanol forming a cofactor-peroxide-alkyl intermediate. This intermediate reacts with the reactive pi-electrons of the substrate, leading to the formation of the alkoxyphenols and the release of the fluorine substituent as fluoride anion.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP622628	4-Ethoxyphenol		622-62-8	Price

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