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Molecules 2005, 10(1), 201-216; doi:10.3390/10010201

Oxidative Dearomatization of Phenols and Anilines via λ3- and λ5-Iodane-Mediated Phenylation and Oxygenation

Institut Européen de Chimie et Biologie and Laboratoire de Chimie des Substances Végétales, Centre de Recherche en Chimie Moléculaire, Université Bordeaux 1, France
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Received: 28 May 2004 / Accepted: 25 July 2004 / Published: 31 January 2005
(This article belongs to the Special Issue Hypervalent Iodine)
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Abstract

Treatment of 2-methylphenols with chloro(diphenyl)-λ3-iodane led to theirregioselective dearomatizing 2-phenylation into cyclohexa-2,4-dienone derivatives via aproposed ligand coupling reaction. In the same vein of investigation, treatment of2-methylanilines with the λ5-iodane 2-iodoxybenzoic acid IBX reagent led to theirregioselective dearomatization into previously undescribed ortho-quinol imines.
Keywords: Iodanes; phenols; anilines; dearomatization; cyclohexadienones; orthoquinol imines Iodanes; phenols; anilines; dearomatization; cyclohexadienones; orthoquinol imines
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Quideau, S.; Pouységu, L.; Ozanne, A.; Gagnepain, J. Oxidative Dearomatization of Phenols and Anilines via λ3- and λ5-Iodane-Mediated Phenylation and Oxygenation. Molecules 2005, 10, 201-216.

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