Skip to main content
SpringerLink
Log in

Reactions of 1-Halo-4-nitroanthraquinones with C-Nucleophiles

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

1-Fluoro-4-nitroanthraquinone reacts with C-nucleophiles, yielding the corresponding fluorine replacement products. Reactions of 1-chloro-4-nitroanthraquinone with the same nucleophiles result in formation of mixtures of dechlorination and denitration products whose ratio is determined by both charge and orbital interactions. Steric structure of the nucleophile can also affect the regioselectivity of substitution.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. Kurdyumova, T.N., Organicheskie poluprodukty i krasiteli. Khimiya antrakhinonov (Organic Intermediate Products and Dyes. Chemistry of Anthraquinones), Moscow: Khimiya, 1969, no. 4, pp. 94-104.

    Google Scholar 

  2. Slosar, J., Sterba, V., and Vecera, M., Collect. Czech. Chem. Commun., 1969, vol. 34, no. 9, pp. 2763-2770.

    Google Scholar 

  3. Klimenko, L.S., Mainagashev, I.Ya., Leonenko, E.V., and Gritsan, N.P., Izv. Ross. Akad. Nauk, Ser. Khim., 1995, no. 10, pp. 1988-1994.

  4. Tabatskaya, A.A., Beregovaya, I.V., and Vlasov, V.M., Russ. J. Org. Chem., 1998, vol. 34, no. 6, pp. 861-866.

    Google Scholar 

  5. Tabatskaya, A.A. and Vlasov, V.M., Russ. J. Org. Chem., 1997, vol. 33, no. 5, pp. 700-704.

    Google Scholar 

  6. Gorelik, M.V., Titova, S.P., and Kanor, M.A., Zh. Org. Khim., 1992, vol. 28, no. 11, pp. 2294-2300.

    Google Scholar 

  7. Stahly, G.P., J. Org. Chem., 1985, vol. 50, no. 17, pp. 3091-3094; Buncel, E. and Manderville, R.A., J. Phys. Org. Chem., 1993, vol. 6, no. 2, pp. 71-82.

    Google Scholar 

  8. Bordwell, F.G. and Hughes, D.L., J. Org. Chem., 1983, vol. 48, no. 13, pp. 2206-2215.

    Google Scholar 

  9. Cervera, M., Marquet, J., and Martin, X., Tetrahedron, 1996, vol. 52, no. 7, pp. 2557-2564.

    Google Scholar 

  10. Brooke, G.M., Chambers, R.D., Drury, C.J., and Bower, M.J., J. Chem. Soc., Perkin Trans. 1, 1993, no. 18, pp. 2201-2209.

  11. Bliznyuk, A.A. and Voityuk, A.A., Zh. Strukt. Khim., 1986, vol. 27, no. 4, pp. 190-191.

    Google Scholar 

  12. Tabatskaya, A.A. and Vlasov, V.M., Zh. Org. Khim., 1991, vol. 27, no. 6, pp. 1285-1297.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Siberian Division, Russian Academy of Sciences, Vorozhtsov Novosibirsk Institute of Organic Chemistry, pr. Akademika Lavrent'eva 9, Novosibirsk, 630090, Russia

    A. A. Tabatskaya & I. V. Beregovaya

Authors
  1. A. A. Tabatskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. V. Beregovaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tabatskaya, A.A., Beregovaya, I.V. Reactions of 1-Halo-4-nitroanthraquinones with C-Nucleophiles. Russian Journal of Organic Chemistry 37, 410–415 (2001). https://doi.org/10.1023/A:1012444810981

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1012444810981

Keywords

Search

Navigation