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Synthesis of brominated 2-(tert-butyl-NNO-azoxy)anilmes

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Abstract

2-(tert-Butyl-NNO-azoxy)aniline was prepared by selective reduction of 2-(tert-butyl-NNO-azoxy)nitrobenzene. Its bromination yielded the correspondingpara-bromo- andortho, para-dibromoanilines (3a,b).meta-Bromoanilines (6a,b) were synthesized by selective replacement of theortho-bromine atoms in ortho,para-bromo(tert-butylazoxy)benzenes (5a,b) by ammonia in toluene under pressure.

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References

  1. 1.

    A. M. Churakov, S. L. Ioffe, and V, A. Tartakovsky,Mendeleev Commun., 1991, 101.

  2. 2.

    E. T. Apasov, B. A. Dzhetigenov, Yu. A. Strelenko, A. V. Kalinin, and V. A. Tartakovsky,Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 1394 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991,40, 1234 (Engl. Transl.)].

  3. 3.

    R. C. Zawalski and P. Kovacic,J. Org. Chem., 1979,44, 2130.

  4. 4.

    H. J. den Hertog and C. Jouwersma,Rec. Trav. Chim. Pays-Bas, 1953,72, 44.

  5. 5.

    T. J. De Bur and P. Dirks, inThe Chemistry of the Nitro and Nitroso Groups, Part 1, Ed. H. Feuer, Interscience Publ., Wiley & Sons, New York-London, 1970.

  6. 6.

    D. E. Ewing,Org. Magn. Reson., 1979,12, 499.

  7. 7.

    W. Gottardi,Monatsh. Chem., 1973,104, 1681.

  8. 8.

    W. Ando and H. Tsumaki,Synthesis, 1982, 263.

  9. 9.

    R. R. Holmes and R. P. Bayer,J. Am. Chem. Soc., 1960,82, 3454.

  10. 10.

    E. Bamberger,Ber., 1903,36, 3803.

  11. 11.

    F. B. Mallory, K. E. Schneller, and C. S. Wood,J. Org. Chem., 1961,26, 3312.

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1620–1623, September, 1994.

This work was carried out with the financial support of the Russian Foundation for Basic Research (Project No. 93-03-18461).

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Churakov, A.M., Smirnov, O.Y., Ioffe, S.L. et al. Synthesis of brominated 2-(tert-butyl-NNO-azoxy)anilmes. Russ Chem Bull 43, 1532–1535 (1994). https://doi.org/10.1007/BF00697142

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Key words

  • aromatic amino, azoxy, nitro, and nitroso compounds
  • selective reduction of a nitro group
  • bromination
  • selective nucleophilic substitution