Free-Radical Reagents. 2. Oxidation and Addition Products from the Reaction of Di-tert-butyliminoxyl with Phenols

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The blue, persistent free-radical di-tert-butyliminoxyl, t-Bu2C=NO (1), oxidizes p-hydroquinones and catechol in organic solvents to the corresponding quinones in good yield. With simple phenols, the reaction takes three pathways. 2-Naphthol and 9-phenanthrol are oxidized to the corresponding o-quinones, while 1-naphthol, phenol, and 2,6-di-tert-butylphenol give 4,4-disubstituted oxime ethers. Para-substituted phenols afford cyclohexadienones with one di-tert-butyliminoxyl at the original para position. Some of these adducts can be prepared by cooxidation of 1–H and the phenol with ceric ion. Rate constants for some of the reactions of 1 with phenols have been measured by kinetic EPR spectroscopy. © 1986, American Chemical Society. All rights reserved.

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Journal of Organic Chemistry