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Oxidative cross-coupling of some 2,6- and N,N-disubstituted aniline derivatives with 4-aminophenol mediated by cerium(IV) ions in aqueous perchloric acid

Durch Cer(IV)-Ionen induzierte oxidative Kreuzkupplung einiger 2,6- und N,N-disubstituierter Anilinderivate mit 4-Aminophenol in wässriger Perchlorsäure

  • Anorganische Und Physikalische Chemie
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Summary

The mechanism of the oxidation of mixtures of 2,6-dimethylaniline (1), N,N-dimethylaniline (2), 2,6-diethylaniline (3), N,N-diethylaniline (4), N-methylaniline (5), 2,6-difluoroaniline (6), and 2,3,5,6-tetrafluoroaniline (7) with 4-aminophenol (8) by cerium(IV) ions in aqueous perchloric acid has been investigated. The indoaniline salts [O=C6H4=N-C6H2(R 1)2NH(R 2)2]+ClO −4 (R 1=H,R 2=CH3, C2H5 orvice versa) are formed as intermediates in the cross-coupling reaction; they undergo oxidation to imino-4-benzoquinone (9) and its corresponding derivatives by cerium(IV) ions in high yields. The mechanism of this process is discussed.

Zusammenfassung

Die Oxidation von Mischungen von 2,6-Dimethylanilin (1), N,N-Dimethylanilin (2), 2,6-Diethylanilin (3), N,N-Diethylanilin (4), N-Methylanilin (5), 2,6-Difluoranolin (6) und 2,3,5,6-Tetrafluoranilin (7) mit 4-Aminophenol (8) durch Cer(IV)-Ionen in wässriger Perchlorsäure wurde untersucht. Als Zwischenprodukte der Kreuzkupplungsreaktion treten die Indoanilinsalze [O=C6H4=N-C6H2(R 1)2NH(R 2)2]+ClO −4 (R 1=H,R 2=CH3, C2H5 oder umgekehrt) auf. Diese werden durch Cer(IV)-Ionen in hohen Ausbeuten zu Imino-4-benzochinon (9) und seinen entsprechenden Derivaten oxidiert. Der Mechanismus dieses Vorgangs wird diskutiert.

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References

  1. Liotta D, Arabiser J, Short JW, Saindane M (1983) J Org Chem48: 2932

    Google Scholar 

  2. Katsoulis DE, Pope MT, (1989) J Chem Soc Dalton Trans 1483

  3. Shimizu M, Orita H, Hayakawa T, Takehira K (1989) Tetrahedron Lett30(4): 471

    Google Scholar 

  4. Dockal ER, Cass QB, Brocksom TJ, Brocksom U, Correa AG (1985) Synthetic Comm15(11): 1033

    Google Scholar 

  5. Hussain A, Jenkins TC, Perkins MJ, (1979) J Chem Soc Perkin I, 2809

  6. Minisci F, Citterio A, Vismara E, Fontana F, De Bernardinis S (1989) J Org Chem54: 728

    Google Scholar 

  7. Zimmer H, Lankin DC, Horgan SW (1971) Chem Rev71: 229

    Google Scholar 

  8. McKillop A, Perry DM, Edwards M, Autus S, Farkas L, Nogrady N, Taylor EC J (1976) Org Chem41: 282

    Google Scholar 

  9. Dziegieć J (1997) Zh Obshch Khim (in press)

  10. Ignaczak M, Dziegieć J, Grzejdziak A, Seliger P (1993) Elektrokhim29(N7): 878

    Google Scholar 

  11. Seliger P, Grzejdziak A, Dziegiec J (1994) Elektrokhim30(N12): 1482

    Google Scholar 

  12. Stewart JJP (1990) Journal of Computer-Aided Molecular Design4: 1

    Google Scholar 

  13. Smith GF, Getz C (1940) Ind Eng Chem Anal Ed12: 339

    Google Scholar 

  14. Dziegieć J (1994) Polish J Appl Chem38(1): 43

    Google Scholar 

  15. Dziegieć J, Seliger P (1995) Polish J Appl Chem39(3): 95

    Google Scholar 

  16. Desider GP, Lepri L, Heimler D (1974) J Electroanal Chem52: 93

    Google Scholar 

  17. Bacon J, Adams RN (1968) J Am Chem Soc90: 6596

    Google Scholar 

  18. Hand RL, Nelson RF (1974) J Am Chem Soc96: 850

    Google Scholar 

  19. Hand RL, Nelson RF (1978) Electrochem Soc125: 1059

    Google Scholar 

  20. Sharma LR, Manchanda AK, Singh G, Verma RS (1982) Electrochim Acta27: 223

    Google Scholar 

  21. Ignaczak M, Dziegieć J (1989) Kinet Kataliz30(5): 1026

    Google Scholar 

  22. Nickel UJ (1986) Imag Tech12: 181

    Google Scholar 

  23. Fisher R (1914) US Pat 1,102,028

  24. Niwa T, Murata Y, Maeda S (1988) Mitsubishi Chem Ind Ltd DE 3,524,516, pr 7

  25. Koechlin J, Witt T (1881) German Patent No. 15, 915

  26. Bayrac A (1897) Ann Chim7(10): 18

    Google Scholar 

  27. Gnehm F, Bots R (1904) J Prakt Chem69: 162

    Google Scholar 

  28. Heller F (1912) Ann392: 16

    Google Scholar 

  29. Fieser L, Thompson HT (1939) J Am Chem Soc61: 376

    Google Scholar 

  30. Vittum PW, Brown GH (1946) J Am Chem Soc68: 2235

    Google Scholar 

  31. Vittum PW, Brown GH (1947) J Am Chem Soc69: 152

    Google Scholar 

  32. Vittum PW, Brown GH (1949) J Am Chem Soc71: 2287

    Google Scholar 

  33. Dziegiec J (1985) Chem Stos29: 263

    Google Scholar 

Download references

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Authors and Affiliations

  1. Department of General and Inorganic Chemistry, University of Łódź, PL-90136, Łódź, Poland

    S. Domagała & J. Dziegieć

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  1. S. Domagała
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  2. J. Dziegieć
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Domagała, S., Dziegieć, J. Oxidative cross-coupling of some 2,6- and N,N-disubstituted aniline derivatives with 4-aminophenol mediated by cerium(IV) ions in aqueous perchloric acid. Monatsh Chem 128, 749–757 (1997). https://doi.org/10.1007/BF00807085

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  • DOI: https://doi.org/10.1007/BF00807085

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