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

Author(s): S. Quideau | L. Pouységu | A. Ozanne | J. Gagnepain

Journal: Molecules
ISSN 1420-3049

Volume: 10;
Issue: 1;
Start page: 201;
Date: 2005;
Original page

Keywords: Iodanes | phenols | anilines | dearomatization | cyclohexadienones | orthoquinol imines

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.
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