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Anion-radicals in reaction of p-nitrochlorobenzene with nucleophilic reagents

  • Organic and Biological Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    A study was made of the kinetic rules for the formation of anion-radicals (AR) in the reactions of p-nitrochlorobenzene with KOH and sodium methylate. The AR of p-nitrochlorobenzene are formed in both reactions and, in addition, the AR of p-nitroanisole are formed in the reaction with CH3ONa.

  2. 2.

    It was discovered that p-nitroanisole exerts an initiating effect in the reaction of p-nitrochlorobenzene with CH3ONa.

  3. 3.

    Tetracyanoethylene and tetracyanoquinodimethane exhibit the reaction of p-nitrochlorobenzene with KOH. The scheme of a chain process was proposed for the reactions of aromatic nitro compounds with nucleophilic reagents.

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Literature cited

  1. S. M. Shein, L. V. Bryukhovetskaya, N. M. Bazhin, V. N. Panfilov, and V. V. Voevodskii, Abstracts of Eighth International Symposium on Free Radicals [in Russian], Novosibirsk (1967), p. 167.

  2. S. M. Shein, L. V. Bryukhovetskaya, F. V. Pishchugin, V. F. Starichenko, V. N. Panfilov, and V. V. Voevodskii, Zh. Strukt. Khim.,11, 243 (1970).

    Google Scholar 

  3. S. M. Shein, L. V. Bryukhovetskaya, A. D. Khmelinskaya, V. F. Starichenko, and T. M. Ivanova, Reaktsionnaya Sposobnost Organicheskikh Soedinenii, Tartuskii Gos. Univ., No. 4 (22), 1087 (1969).

    Google Scholar 

  4. L. A. Blyumenfel'd, L. V. Bryukhovetskaya, G. V. Fomin, and S.M. Shein, Zh. Fiz. Khim.,44, 931 (1970).

    Google Scholar 

  5. N. N. Vorozhtsov, Principles of Synthesis of Intermediates and Dyes [in Russian], Goskhimizdat (1955), p. 373.

  6. F. M. Vainshtein, I. I. Kukhtenko, E. I. Tomilenko, and E. A. Shilov, Zh Org. Khim.,3, 1654 (1967); L. F. Ovechkina, V. L Gunar, and S. I. Zav'yalov, Izv. Akad. Nauk SSSR, Ser. Khim., 2035 (1969).

    Google Scholar 

  7. N. M. Emanuel', E. T. Denisov, and Z. K. Maizus, Chain Reactions for Oxidation of Hydrocarbons in the Liquid Phase [in Russian], Nauka (1965), pp. 23, 49, 273; E. T. Denisov and N. M. Emanuel', Usp. Khim.,27, 392 (1958).

  8. P. Ashmore, Catalysis and Inhibition of Chemical Reactions [Russian translation], Mir (1966), p. 359.

  9. F. E. Stewart, M. Eisner, and W. P. Carper, J. Chem. Phys.,44, 2866 (1966); F. E. Stewart and M. Eisner, Mol. Phys.,12, 173 (1967); R. M. Hainer, A. Pryce, and L. Shields, J. Chem. Soc., B, 820 (1970).

    Google Scholar 

  10. E. Kozover, New Problems in Physical Organic Chemistry [Russian translation], Mir (1969), p. 36; T. Cairns, R. Carboni, D. Coffman, V. Engelhartt, R. Heckert, E. Little, E. McGeer, B. McKusick, W. Middleton, R. Scribner, C. Theobald, and H. Winberg, J. Am. Chem. Soc.,80, 2775 (1958).

  11. N. M, Emanuel' and D. G. Knorre, Course in Chemical Kinetics [in Russian], Vysshaya Shkola (1962), p. 309.

  12. S. M. Shein, A. D. Khmelinskaya, and V. V. Brovko, Zh. Org. Khim.,6, 781 (1970).

    Google Scholar 

  13. V. F. Starichenko, V. P. Sokolov, and S. M. Shein, Izv. Akad. Nauk SSSR, Ser. Khim., 1839 (1971).

  14. R. Foster and C. A. Fyfe, Rev. Pure Appl. Chem.,16, 61 (1966); N. J. Strauss, Chem. Rev.,70, 667 (1970).

    Google Scholar 

  15. N. M. Katkova, V. S. Vainer, V. V. Brovko, S. M. Shein, and Yu. N. Molin, Kinetika i Kataliz,11, 65 (1970); S. N. Selenin and M. L. Khidekel, Usp. Khim.,39, 209 (1970).

    Google Scholar 

  16. G. A. Russell and W. C. Danen, J. Am. Chem. Soc.,88, 5663 (1966).

    Google Scholar 

  17. N. Kornblum, R. E. Michel, and R. C. Kerber, J. Am. Chem. Soc.,88, 5662 (1966).

    Google Scholar 

  18. V. A. Tolkachev and A. I. Mikhailov, Pribory i Tekhn. Eksperim.,6, 95 (1964); Yu. N. Molin, V. M. Chibrikin, V. A. Shabalkin, and V. F. Shuvalova, Zavod. Lab.,32, 933 (1966).

    Google Scholar 

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1594–1601, July, 1973.

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Shein, S.M., Bryukhovetskaya, L.V. & Ivanova, T.M. Anion-radicals in reaction of p-nitrochlorobenzene with nucleophilic reagents. Russ Chem Bull 22, 1543–1549 (1973). https://doi.org/10.1007/BF00930058

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  • DOI: https://doi.org/10.1007/BF00930058

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