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Reaction of N,N′-disubstituted 1,4-benzoquinone diimines with sodium arenesulfinates

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Abstract

Radical anion 1,6-addition path in the reactions of N,N′-disubstituted 1,4-benzoquinone diimines with sodium arenesulfinates is favored by increase of the electron-donating power of the substituent in the para position of arenesulfinate ion and redox potential of the initial 1,4-benzoquinone diimine.

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References

  1. Adams, R. and Moje, W., J. Am. Chem. Soc., 1952, vol. 74, p. 5560.

    Article  CAS  Google Scholar 

  2. Adams, R. and Samuels, W.P., J. Am. Chem. Soc., 1955, vol. 77, p. 5383.

    Article  CAS  Google Scholar 

  3. Adams, R., Young, T.E., and Short, R.W.P., J. Am. Chem. Soc., 1954, vol. 76, p. 1114.

    Article  CAS  Google Scholar 

  4. Adams, R. and Acker, D.S., J. Am. Chem. Soc., 1952, vol. 74, p. 3657.

    Article  CAS  Google Scholar 

  5. Adams, R. and Nair, M.D., J. Am. Chem. Soc., 1956, vol. 78, p. 5927.

    Article  CAS  Google Scholar 

  6. Adams, R. and Young, T.E., J. Am. Chem. Soc., 1953, vol. 75, p. 3235.

    Article  CAS  Google Scholar 

  7. Adams, R. and Nair, M.D., J. Am. Chem. Soc., 1956, vol. 78, p. 5932.

    Article  CAS  Google Scholar 

  8. Burmistrov, K.S. and Burmistrov, S.I., Vopr. Khim. Khim. Technol., 1981, no. 65, p. 42.

    Google Scholar 

  9. Konovalova, S.A., Avdeenko, A.P., Pirozhenko, V.V., Ledeneva, O.P., and Santalova, A.A., Russ. J. Org. Chem. 2014, vol. 50, p. 1283.

    Article  CAS  Google Scholar 

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

    CAS  Google Scholar 

  11. Burmistrov, K.S. and Burmistrov, S.I., Zh. Org. Khim., 1980, vol. 16, p. 1487.

    CAS  Google Scholar 

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

    Google Scholar 

  13. Zefirov, Yu.V., Kristallografiya, 1997, vol. 42, p. 936.

    CAS  Google Scholar 

  14. 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.

    Google Scholar 

  15. Adams, R. and Nagarkatti, A.S., J. Am. Chem. Soc., 1950, vol. 72, p. 4601.

    Article  CAS  Google Scholar 

  16. Boger, D.L. and Zarrinmayeh, H., J. Org. Chem., 1990, vol. 55, p. 1379.

    Article  CAS  Google Scholar 

  17. Adams, R. and Reifschneider, W., Bull. Soc. Chim. Fr., 1958, vol. 25, p. 23.

    Google Scholar 

  18. Konovalova, S.A., Avdeenko, A.P., Pirozhenko, V.V., Goncharova, S.A., Shishkin, O.V., and Palamarchuk, G.V., Russ. J. Org. Chem., 2014, vol. 50, p. 1465.

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

  20. Willstatter, R. and Pfannenstiel, A., Ber., 1905, vol. 38, p. 2244.

    Article  CAS  Google Scholar 

  21. Adams, R. and Anderson, J., J. Am. Chem. Soc., 1950, vol. 72, p. 5154.

    Article  CAS  Google Scholar 

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Authors and Affiliations

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

    S. A. Konovalova, A. P. Avdeenko & A. A. Santalova

  2. Institute for Single Crystals, National Academy of Sciences of Ukraine, pr. Lenina 60, Kharkiv, 61001, Ukraine

    G. V. Palamarchuk, V. V. D’yakonenko & O. V. Shishkin

  3. Karazin Kharkiv National University, pl. Svobody 4, Kharkiv, 61022, Ukraine

    O. V. Shishkin

Authors
  1. S. A. Konovalova
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  2. A. P. Avdeenko
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  3. A. A. Santalova
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  4. G. V. Palamarchuk
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  5. V. V. D’yakonenko
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  6. O. V. Shishkin
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Corresponding author

Correspondence to S. A. Konovalova.

Additional information

Original Russian Text © S.A. Konovalova, A.P. Avdeenko, A.A. Santalova, G.V. Palamarchuk, V.V. D’yakonenko, O.V. Shishkin, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 1, pp. 48–56.

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Konovalova, S.A., Avdeenko, A.P., Santalova, A.A. et al. Reaction of N,N′-disubstituted 1,4-benzoquinone diimines with sodium arenesulfinates. Russ J Org Chem 51, 42–50 (2015). https://doi.org/10.1134/S1070428015010078

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  • DOI: https://doi.org/10.1134/S1070428015010078

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