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1-Oxo-2,2,6,6-Tetramethyl-4-Chloropiperidinium Perchlorate. a New Facile Oxidant for Phenol Coupling

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The title compound (1) oxidizes 2,6-di-tert-butylphenol (2), 2, 6-di-tert-butyl-4-methylphenol (3), 2,6-di-tert-butyl-4-(diphercylmethyl)phenol (4), and β-naphthol (5), to quinones in good yield under mild conditions in acetonitrile. For unsubstituted phenols the reaction takes place in two ways, phenol (6) is oxidized to quinhydrone (7), while the oxidation products of the phenols, α-naphthol, catechol and 2,4-dihydroxyl-naphthol were only polymers.

Affiliations: 1: Department of Chemistry Lanzhou University Lanzhou, Gansu 730000, CHINA


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