1-oxo-2,2,6,6-tetramethyl-4-chloropiperidinium perchlorate. A new facile oxidant for phenol coupling (original) (raw)

Abstract

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-(dipnenylmethyl)phenol (4), and p-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.

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Author notes

1. H. -X. Guo
   Present address: Shanghai Institute of Organic Chemistry, 345 Ling-ling Lu, 200032, Shanghai, China

Authors and Affiliations

1. Department of Chemistry, Lanzhou University, 730000, Lanzhou, Gansu, China
   H. -X. Guo, Y. -C. Liu, Z. -L. Liu & C. -L. Li

Authors

1. H. -X. Guo
2. Y. -C. Liu
3. Z. -L. Liu
4. C. -L. Li

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Guo, H.X., Liu, Y.C., Liu, Z.L. et al. 1-oxo-2,2,6,6-tetramethyl-4-chloropiperidinium perchlorate. A new facile oxidant for phenol coupling.Res Chem Intermed 17, 137–143 (1992). https://doi.org/10.1163/156856792X00100

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• Received: 11 February 1992
• Accepted: 03 April 1992
• Issue date: June 1992
• DOI: https://doi.org/10.1163/156856792X00100

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