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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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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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References

  1. V.A. Goluber, VD. Sholle, and E.G. Rozantsev, Izv Akad Nauk USSR Ser. Khim., 184(1970); 188(1970).

  2. T. Miyazawa, T. Endo, S. Shiihashi, and W. Okawarw, J. Org. Chem., 50(1985)1332.

    Article  CAS  Google Scholar 

  3. M.F. Semmehalk, C.S. Chou, and D.A. Corees, J. Am. Chem. Soc., l05(1983)4492.

    Article  Google Scholar 

  4. Y.-C. Liu, H.-X. Guo, and Z.-L. Liu, Acta Chimica Sinica, 187(1991).

  5. Y.-C. Liu, Z.-L. Liu, and H.-X. Guo, Chem. J. Chinese Univ. Engl. Ed., 4(1988)90.

    Google Scholar 

  6. M. Nego, K.R. Larson, and G.D. Mendenhall, J. Org. Chem., 51(1986)5390.

    Article  Google Scholar 

  7. a) K. Dimorth in F.L. Boschke (Ed.), Topics in Current Chemistry, Vol. 129, Springer-Vellag, Berlin, Heidelberg, 1985, p.99. b) H. Musso, Angew. Chem. Internat. Ed., 2(1963)723.

    Google Scholar 

  8. D.D. Perrin, W.L.F. Armonego, and D.R. Perrin, Purification of Laboratory Chemicals, 2nd. Ed., Permagnon Press, N.Y., 1976.

    Google Scholar 

  9. E. Mueller (Ed.), Methodnn der Organischen Chemie, Houben-Weyl, 4th Ed., Vol. VIc, Part 1 and 2, G. Thieme Verlag, Stuttgart, 1976.

    Google Scholar 

  10. S. Patai (Ed.), The Chemistry of the Hydroxyl Group, Part 1 and 2, Interscienee Publ., London, 1971.

    Google Scholar 

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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
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  2. Y. -C. Liu
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  3. Z. -L. Liu
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  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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  • DOI: https://doi.org/10.1163/156856792X00100

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