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Reactions of cyclopropanes with potassium dihaloiodates

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Abstract

Reactions of potassium dihaloiodates with arylcyclopropanes and polycyclic compounds containing a cyclopropane fragment characterized by different degrees of strain lead to formation of mixed 1,3-halogenation products. If iodohalogenation should give rise to products having a iodine atom in the benzylic position, 1,3-dichloro or 1,3-dibromo derivatives are formed. Iodohalogenation of exo-tricyclo[3.2.1.02,4]octane is stereoselective and is accompanied by Wagner-Meerwein rearrangement.

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References

  1. Atkinson, P.H., Cambie, R.C., Dixon, G., Noall, W., Rutledge, S., and Woodgate, D., J. Chem. Soc., Perkin Trans. 1, 1977, p. 230.

  2. Gazzaeva, R.A., Shabarov, Yu.S., and Saginova, L.G., Zh. Org. Khim., 1984, vol. 20, p. 220.

    CAS  Google Scholar 

  3. Pisanova, E.V., Shabarov, Yu.S., and Saginova, L.G., Zh. Org. Khim., 1981, vol. 17, p. 1337.

    Google Scholar 

  4. Saginova, L.G., Bondarenko, O.B., Gazzaeva, R.A., and Shabarov, Yu.S., Zh. Org. Khim., 1985, vol. 21, p. 526.

    CAS  Google Scholar 

  5. Saginova, L.G. and Shabarov, Yu.S., Zh. Org. Khim., 1977, vol. 13, p. 2535.

    CAS  Google Scholar 

  6. Zefirov, N.S., Sereda, G.A., Sosonyuk, S.E., Zyk, N.V., and Lihomanova, T.I., Synthesis, 1995, p. 1359.

  7. Sosonyuk, S.E., Cand. Sci. (Chem.) Dissertation, Moscow, 1999.

  8. Fialkov, Ya.I., Mezhgaloidnye soedineniya (Interhalogen Compounds), Kiev: Akad. Nauk USSR, 1958, p. 395.

    Google Scholar 

  9. Olah, G.A., Bollinger, J.M., Mo, Y.K., and Brinich, J.M., J. Am. Chem. Soc., 1972, vol. 94, p. 1164.

    Article  CAS  Google Scholar 

  10. Fokin, A.A., Schreiner, P.R., Gunchenko, P.A., Peleshanko, S.A., Shubina, T.E., Isaev, S.D., Tarasenko, P.V., Kulik, N.I., Schiebel, H.-M., and Yurchenko, A.G., J. Am. Chem. Soc., 2000, vol. 122, p. 7317.

    Article  CAS  Google Scholar 

  11. Todres, Z.V., Ion-radikaly v organicheskom sinteze (Radical Ions in Organic Synthesis), Moscow: Khimiya, 1986, p. 240.

    Google Scholar 

  12. Potapov, V.M., Stereokhimiya (Stereochemistry), Moscow: Khimiya, 1988, p. 124.

    Google Scholar 

  13. Stewart, J.J.P., J. Comput. Chem., 1989, vol. 10, p. 209.

    Article  CAS  Google Scholar 

  14. Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972.

    Google Scholar 

  15. Bräuer, G., Handbuch der präparativen anorganischen Chemie, Stuttgart: Enke, 1981. Translated under the title Rukovodstvo po neorganicheskomu sintezu, Moscow: Mir, 1985, vol. 2, p. 343.

    Google Scholar 

  16. Grigor’ev, E.V., Saginova, L.G., and Kleimenova, I.Yu., Khim. Geterotsikl. Soedin., 2003, p. 1053.

  17. Miranda, M.A., Pérez-Prieto, J., Font-Sanchis, E., Kónya, K., and Scaiano, J.C., J. Org. Chem., 1997, vol. 62, p. 5713.

    Article  CAS  Google Scholar 

  18. Grigor’ev, E.V. and Saginova, L.G., Khim. Geterotsikl. Soedin., 2003, p. 120.

  19. LaLonde, R.T., Ferrara, P.B., and Debboli, A.D., J. Org. Chem., 1972, vol. 37, p. 1094.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Vorob’evy gory 1, Moscow, 119992, Russia

    N. V. Zyk, A. Yu. Gavrilova, O. B. Bondarenko & O. A. Mukhina

  2. Moscow State Pedagogical University, Moscow, Russia

    V. N. Tikhanushkina

Authors
  1. N. V. Zyk
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  2. A. Yu. Gavrilova
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  3. O. B. Bondarenko
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  4. O. A. Mukhina
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  5. V. N. Tikhanushkina
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Correspondence to A. Yu. Gavrilova.

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Original Russian Text © N.V. Zyk, A.Yu. Gavrilova, O.B. Bondarenko, O.A. Mukhina, V.N. Tikhanushkina, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 3, pp. 347–361.

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Zyk, N.V., Gavrilova, A.Y., Bondarenko, O.B. et al. Reactions of cyclopropanes with potassium dihaloiodates. Russ J Org Chem 47, 340–354 (2011). https://doi.org/10.1134/S1070428011030031

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  • DOI: https://doi.org/10.1134/S1070428011030031

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