Skip to main content
SpringerLink
Log in

Halogenation of n-substituted p-quinone monoimines and p-quinone monooxime esters: VIII. Halogenation of N-aroyl(arylsulfonyl)-2,6-di-tert-butyl-1,4-benzoquinone monoimines and their reduced forms

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

Abstract

Chlorination of N-aroyl(arylsulfonyl)-2,6-di-tert-butyl-1,4-benzoquinone imines gave Z and E isomers of 4-arylsulfonylimino-2,6-di-tert-butyl-5,6-dichlorocyclohex-2-en-1-ones and Z isomers of 4-aroyl-(arylsulfonyl)imino-2,6-di-tert-butyl-5,5,6-trichlorocyclohex-2-en-1-ones, in which the tert-butyl group on the sp 3-hybridized carbon atom occupies exclusively the axial position. The formation of Z/E-isomeric structures is related to configurational stability of the chlorination products. The chlorination of 4-aroylamino-2,6-di-tertbutylphenols was found to be accompanied by replacement of one tert-butyl group by chlorine atom with formation of 4-aroylimino-6-tert-butyl-2,3,5,6-tetrachlorocyclohex-2-en-1-ones.

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. Avdeenko, A.P., Pirozhenko, V.V., Shishkin, O.V., Shishkina, S.V., Konovalova, S.A., and Ludchenko, O.N., Russ. J. Org. Chem., 2008, vol. 44, p. 542.

    Article  CAS  Google Scholar 

  2. Pirozhenko, V.V. and Avdeenko, A.P., Russ. J. Org. Chem., 1995, vol. 31, p. 1514.

    Google Scholar 

  3. Belov, V.V., Loban’, S.V., Burmistrov, K.S., and Prosyanik, A.V., Zh. Org. Khim., 1983, vol. 19, p. 825.

    CAS  Google Scholar 

  4. Avdeenko, A.P. and Konovalova, S.A., Russ. J. Org. Chem., 2006, vol. 42, p. 349.

    Article  CAS  Google Scholar 

  5. Polo, C., Ramos, V., and Torroba, T., Tetrahedron, 1998, vol. 54, p. 223.

    Article  CAS  Google Scholar 

  6. Zefirov, Yu.V. and Zorkii, P.M., Usp. Khim., 1989, vol. 58, p. 713.

    CAS  Google Scholar 

  7. Burgi, H.-B. and Dunitz, J.D., Structure Correlation, Weinheim: VCH, 1994, vol. 2, p. 741.

    Google Scholar 

  8. Avdeenko, A.P., Konovalova, S.A., Il’chenko, A.Ya., and Glinyanaya, N.M., Russ. J. Org. Chem., 2006, vol. 42, p. 64.

    Google Scholar 

  9. Sheldrick, G.M., SHELXTL PLUS. PC Version. A System of Computer Programs for the Determination of Crystal Structure from X-ray Diffraction Data. Rev. 5.1, 1998.

  10. Blessing, R.H., Acta Crystallogr., Sect. A, 1995, vol. 51, p. 33.

    Article  Google Scholar 

  11. Burmistrov, K.S., Doctoral (Chem.) Dissertation, Dnepropetrovsk, 1990.

  12. Titov, E.A. and Burmistrov, S.I., Ukr. Khim. Zh., 1960, vol. 26, p. 744.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Donbass State Machine-Building Academy, ul. Shkadinova 72, Kramatorsk, 84313, Ukraine

    A. P. Avdeenko, S. A. Konovalova & O. N. Ludchenko

  2. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, Kiev, 02660, Ukraine

    V. V. Pirozhenko

  3. Institute of Single Crystals, National Academy of Sciences of Ukraine, Kharkov, Ukraine

    O. V. Shishkin, G. V. Palamarchuk & R. I. Zubatyuk

Authors
  1. A. P. Avdeenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. V. Pirozhenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. V. Shishkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. G. V. Palamarchuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. R. I. Zubatyuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. S. A. Konovalova
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. O. N. Ludchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. P. Avdeenko.

Additional information

Original Russian Text © A.P. Avdeenko, V.V. Pirozhenko, O.V. Shishkin, G.V. Palamarchuk, R.I. Zubatyuk, S.A. Konovalova, O.N. Ludchenko, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 6, pp. 818–824.

For communication VII, see [1].

Rights and permissions

Reprints and permissions

About this article

Cite this article

Avdeenko, A.P., Pirozhenko, V.V., Shishkin, O.V. et al. Halogenation of n-substituted p-quinone monoimines and p-quinone monooxime esters: VIII. Halogenation of N-aroyl(arylsulfonyl)-2,6-di-tert-butyl-1,4-benzoquinone monoimines and their reduced forms. Russ J Org Chem 44, 807–813 (2008). https://doi.org/10.1134/S1070428008060055

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428008060055

Keywords

Search

Navigation