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Transformations of para-Substituted Benzylcyclopropanes, Allylbenzenes, and Diphenylmethanes under Nitration with Nitric Acid in Acetic Anhydride

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Abstract

Electrophilic nitration of benzylcyclopropanes, allylbenzenes, and diphenylmethanes containing ortho, para-orienting substituents in the para position of the benzene ring results mainly in replacement of the cyclopropylmethyl, allyl, or benzyl group, respectively (ipso substitution). The nitration of 4-cyclopropylallylbenzene is not accompanied by nitrodealkylation, and the products are only 2- and 3-nitro-4-cyclopropylallylbenzenes.

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REFERENCES

  1. Blackstock, D.J., Crethey, I.R., Fischer, A., Hartshorn, M.P., Richards, R.E., Vanghan, J., and Wright, G.J., Tetrahedron Lett., 1970, vol. 11, p. 2793.

    Google Scholar 

  2. Fischer, A., Henderson, G.N., and Thompson, R.J., Aust. J. Chem., 1978, vol. 31, p. 1241.

    CAS  Google Scholar 

  3. Fischer, A. and Roderer, R., Can. J. Chem., 1976, vol. 54, p. 423.

    CAS  Google Scholar 

  4. Fischer, A. and Roderer, R., J. Chem. Soc., Chem. Commun., 1975, no. 19, p. 798.

  5. Fischer, A. and Roderer, R., Can. J. Chem., 1976, vol. 54, p. 3978.

    CAS  Google Scholar 

  6. Shabarov, Yu.S., Mochalov, S.S., Matveeva, N.B., and Stepanova, I.P., Zh. Org. Khim., 1975, vol. 11, p. 568.

    CAS  Google Scholar 

  7. Moodie, R.B., Schofield, K., and Tobin, G.D., J. Chem. Soc., Chem. Commun., 1978, no. 4, p. 180.

  8. Mochalov, S.S., Matveeva, N.B., Stepanova, I.P., and Shabarov, Yu.S., Zh. Org. Khim., 1977, vol. 13, p. 1639.

    CAS  Google Scholar 

  9. Mochalov, S.S., Smirnova, M.M., Geiderikh, A.V., and Shabarov, Yu.S., Vestn. Mosk. Gos. Univ., Ser. 2: Khim., 1987, vol. 28, p. 368.

    Google Scholar 

  10. Karpova, V.V., Mochalov, S.S., and Shabarov, Yu.S., Zh. Org. Khim., 1982, vol. 18, p. 310.

    CAS  Google Scholar 

  11. Fedotov, A.N., Trofimova, E.V., Mochalov, S.S., and Shabarov, Yu.S., Zh. Org. Khim., 1988, vol. 24, p. 1413.

    CAS  Google Scholar 

  12. Shabarov, Yu.S., Potapov, V.K., and Levina, R.Ya., Zh. Obshch. Khim., 1964, vol. 34, p. 3127.

    CAS  Google Scholar 

  13. Shabarov, Yu.S. and Mochalov, S.S., Zh. Org. Khim., 1972, vol. 8, p. 293.

    CAS  Google Scholar 

  14. Shabarov, Yu.S. and Mochalov, S.S., Zh. Org. Khim., 1972, vol. 8, p. 2085.

    CAS  Google Scholar 

  15. Shabarov, Yu.S., Mochalov, S.S., Fedotov, A.N., and Kalashnikov, V.V., Khim. Geterotsikl. Soedin., 1975, p. 1195.

  16. Moodie, R.B., Schofield, K., and Weston, J.B., J. Chem. Soc., Perkin Trans. 2, 1976, p. 1089.

  17. Shabarov, Yu.S. and Mochalov, S.S., Zh. Org. Khim., 1973, vol. 9, p. 56.

    CAS  Google Scholar 

  18. Shabarov, Yu.S. and Mochalov, S.S., Zh. Org. Khim., 1973, vol. 9, p. 2044.

    CAS  Google Scholar 

  19. Mochalov, S.S., Gazzaeva, R.A., Fedotov, A.N., Trofimova, E.V., Trushkov, I.V., and Zefirov, N.S., Russ. J. Org. Chem., 2004, vol. 40, p. 1098.

    CAS  Google Scholar 

  20. Close, W.I., J. Am. Chem. Soc., 1957, vol. 79, p. 1455.

    CAS  Google Scholar 

  21. Klowoen, M.H. and Boelens, M., Recl. Trav. Chim. Pays-Bas, 1960, vol. 79, p. 1022.

    Google Scholar 

  22. Einhorn, J., Pesportes, S.H., Pemerseman, P., and Royer, R., J. Chem. Res., Synop., 1983, p. 98.

  23. Schiemann, G. and Pillarsky, R., Chem. Ber., 1929, vol. 62, p. 3035.

    Google Scholar 

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Authors and Affiliations

  1. Faculty of Chemistry, Lomonosov Moscow State University, Vorob’evy gory 1, Moscow, 119234, Russia

    S. S. Mochalov, A. N. Fedotov, B. P. Archegov, E. V. Trofimova, Yu. S. Shabarov & N. S. Zefirov

  2. Khetagurov North Osetian State University, ul. Vatutina 46, Vladikavkaz, North Osetia, 362015, Russia

    R. A. Gazzaeva

Authors
  1. S. S. Mochalov
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  2. R. A. Gazzaeva
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  3. A. N. Fedotov
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  4. B. P. Archegov
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  5. E. V. Trofimova
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  6. Yu. S. Shabarov
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  7. N. S. Zefirov
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__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 3, 2005, pp. 415–424.

Original Russian Text Copyright © 2005 by Mochalov, Gazzaeva, Fedotov, Archegov, Trofimova, Shabarov, Zefirov.

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Mochalov, S.S., Gazzaeva, R.A., Fedotov, A.N. et al. Transformations of para-Substituted Benzylcyclopropanes, Allylbenzenes, and Diphenylmethanes under Nitration with Nitric Acid in Acetic Anhydride. Russ J Org Chem 41, 406–416 (2005). https://doi.org/10.1007/s11178-005-0179-x

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  • DOI: https://doi.org/10.1007/s11178-005-0179-x

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