Skip to main content
SpringerLink
Log in

Reaction of some N-substituted 1,4-benzoquinone imines with sodium arenesulfinates

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

Abstract

N-Arylsulfonyl, N-aroyl, and N-[arylsulfonylimino(phenyl)methyl] derivatives of 1,4-benzoquinone imine reacted with sodium arenesulfinates to give 1,4-, 1,6-, and 6,1-addition products which were formed according to two concurrent paths: direct nucleophilic addition of arenesulfinate anion to neutral quinone imine molecule and radical ion addition of arenesulfinate radical to radical anion derived from quinone imine.

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. Burmistrov, K.S., Nichvoloda, V.M., Markov, V.I., and Romanchenko, V.A., Zh. Org. Khim., 1986, vol. 22, p. 1306.

    CAS  Google Scholar 

  2. Nichvoloda, V.M., Burmistrov, K.S., and Markov, V.I., Zh. Org. Khim., 1985, vol. 21, p. 1069.

    CAS  Google Scholar 

  3. Nichvoloda, V.M., Alaev, Yu.N., Luk’yanenko, L.V., Markov, V.I., and Burmistrov, K.S., Zh. Org. Khim., 1986, vol. 22, p. 1111; Avdeenko, A.P. and Koshechko, V.G., Zh. Obshch. Khim., 1974, vol. 44, p. 1459.

    CAS  Google Scholar 

  4. Avdeenko, A.P., Konovalova, S.A., Roman’kov, D.A., Burmistrov, K.S., Nichvoloda, V.M., Shishkin, O.V., Zubatyuk, R.I., and Palamarchuk, G.V., Russ. J. Org. Chem., 2009, vol. 45, p. 48.

    Article  CAS  Google Scholar 

  5. Avdeenko, A.P., Konovalova, S.A., Roman’kov, D.A., Ludchenko, O.N., and Marchenko, I.L., Russ. J. Org. Chem., 2009, vol. 45, p. 383.

    Article  CAS  Google Scholar 

  6. Avdeenko, A.P., Konovalova, S.A., Mikhailichenko, O.N., Shelyazhenko, S.V., Pirozhenko, V.V., and Yagupol’skii, L.M., Russ. J. Org. Chem., 2012, vol. 48, p. 221.

    Article  CAS  Google Scholar 

  7. Spravochnik khimika (Chemist’s Handbok), Nikol’skii, B.P., Ed., Leningrad: Khimiya, 1964, 2nd ed., vol. 2, p. 352.

    Google Scholar 

  8. Burmistrov, K.S., Toropin, N.V., Vakulenko, A.V., Yurchenko, A.G., and Markov, V.I., Vopr. Khim. Khim. Tekhnol., 2000, no. 2, p. 30.

    Google Scholar 

  9. Avdeenko, A.P., Pirozhenko, V.V., Yagupol’skii, L.M., and Marchenko, I.L., Russ. J. Org. Chem., 2001, vol. 37, p. 991.

    Article  CAS  Google Scholar 

  10. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Jr., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 03, Revision C.01, Wallingford CT: Gaussian, 2004.

    Google Scholar 

  11. Becke, A.D., Phys. Rev. A, 1988, vol. 38, p. 3098.

    Article  CAS  Google Scholar 

  12. Becke, A.D., J. Chem. Phys., 1993, vol. 98, p. 5648.

    CAS  Google Scholar 

  13. Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, p. 785.

    Article  CAS  Google Scholar 

  14. Volko, S.H., Wilk, L., and Nusair, M., Can. J. Phys., 1980, vol. 58, p. 1200.

    Article  Google Scholar 

  15. Hohenberg, R. and Kohn, W., Phys. Rev., 1964, vol. 136, p. B864.

    Article  Google Scholar 

  16. Parr, R.G. and Yang, W., Density Functional Theory of Atoms and Molecules, New York: Oxford Univ., 1989.

    Google Scholar 

  17. Rassolov, V.A., Pople, J.A., Ratner, M.A., and Windus, T.L., J. Chem. Phys., 1998, vol. 109, p. 1223.

    CAS  Google Scholar 

  18. Rassolov, V.A., Ratner, M.A., Pople, J.A., Redfern, P.C., and Curtiss, L.A., J. Comput. Chem., 2001, vol. 22, p. 976.

    Article  CAS  Google Scholar 

  19. Schleyer, P.v.R., Schreiner, P.R., Allinger, N.L., Clark, T., Gasteiger, J., Kollman, P., and Schaefer, H.F. III, Encyclopedia of Computational Chemistry, Chichester: Wiley, 1998, p. 1792.

    Google Scholar 

  20. Glendening, E.D., Badenhoop, J.K., Reed, A.E., Carpenter, J.E., Bohmann, J.A., Morales, C.M., and Weinhold, F., NBO 5.0, Madison: Theoretical Chemistry Institute, Univ. of Wisconsin, 2001.

    Google Scholar 

  21. Burmistrov, S.I. and Titov, E.A., Zh. Obshch. Khim., 1952, vol. 22, p. 999.

    CAS  Google Scholar 

  22. Avdeenko, A.P., Burmistrov, K.S., Dubina, V.L., and Skripets, V.I., Ukr. Khim. Zh., 1980, vol. 46, p. 1081.

    CAS  Google Scholar 

  23. Whitmore, F.C. and Hamilton, F.H., Org. Synth., 1922, vol. 2, p. 89.

    Article  Google Scholar 

  24. Avdeenko, A.P. and Konovalova, S.A., Russ. J. Org. Chem., 2006, vol. 42, p. 669.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  26. Pirozhenko, V.V., Burmistrov, K.S., Belov, V.V., and Nichvoloda, V.N., Ukr. Khim. Zh., 1992, vol. 58, p. 68.

    CAS  Google Scholar 

  27. Avdeenko, A.P., Konovalova, S.A., and Ludchenko, O.N., Russ. J. Org. Chem., 2009, vol. 45, 1799.

  28. Avdeenko, A.P., Konovalova, S.A., and Ludchenko, O.N., Russ. J. Org. Chem., 2010, vol. 46, p. 1629.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Donbass State Engineering Academy, ul. Shkadinova 72, Kramatorsk, 84313, Ukraine

    S. A. Konovalova, A. P. Avdeenko & I. L. Marchenko

Authors
  1. S. A. Konovalova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. P. Avdeenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. L. Marchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. A. Konovalova.

Additional information

Original Russian Text © S.A. Konovalova, A.P. Avdeenko, I.L. Marchenko, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 7, pp. 991–1003.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Konovalova, S.A., Avdeenko, A.P. & Marchenko, I.L. Reaction of some N-substituted 1,4-benzoquinone imines with sodium arenesulfinates. Russ J Org Chem 50, 973–985 (2014). https://doi.org/10.1134/S1070428014070082

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428014070082

Keywords

Search

Navigation