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Functionalized α-bromocyclopropylmagnesium bromides: Generation and some reactions

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Abstract

Functional derivatives of gem-dibromocyclopropanes (ethers and esters of gemdibromocyclopropylmethanol, 2,2-dibromocyclopropanecarboxylic acids and their esters) undergo partial hydrodebromination at the treatment with isopropyl magnesium bromide (3–6 mol-equiv) in THF and then in methanol at −60°C affording the corresponding monobromides in 64–95% yields. The addition of nonsolvated magnesium bromide to the reaction mixture results in the considerable reduction of the amount of the Grignard reagent (from 6 to 3 mol-equiv). This allows achieving the partial hydrodebromination of 2,2-dibromocyclopropanecarboxylic acids.

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References

  1. Fedorynski, M., Chem. Rev., 2003, vol. 103, p. 1099.

    Article  CAS  Google Scholar 

  2. Jonczyk, A. and Fedorynski, M., Meth. Org. Chem. (Houben-Weyl)., 1997, E17a, p. 589.

    Google Scholar 

  3. Bolesov, I.G., Berd, M.S., Tverezovskii, V.V., and Kostikov, R.R., Sovremennye problemy organicheskoi khimii (Modern Problems of Organic Chemistry), St. Petersburg: Izd. SPb. Gos. Univ., 2001, vol. 13, p. 80.

    Google Scholar 

  4. Baird, M.S., Chem. Commun., 1974, p. 197.

    Google Scholar 

  5. Baird, M.S. and Reese, C.B., Chem. Commun. D, 1970, p. 1519; Regonnet, B. Santelli, M., and Bertrand, M., Bull. Soc. Shim., 1973, p. 3119.

    Google Scholar 

  6. Baird, M.S., Huber, F.A., Tverezonsky, V.V., and Bolesov, I.G., Tetrahedron Lett., 1998, vol. 39, p. 9081.

    Article  CAS  Google Scholar 

  7. Baird, M.S., Licence, P., Tverezovsky, V.V., Bolesov, I.G., and Slegg, W. Tetrahedron., 1999, vol. 55, p. 2773.

    Article  CAS  Google Scholar 

  8. Seyferth, D. and Lambert, J.R.L., J. Organometal. Chem., 1975, vol. 88, p. 287.

    Article  CAS  Google Scholar 

  9. Seyferth, D. and Prokai, B., J. Org. Chem., 1966, vol. 31, p. 1702.

    Article  CAS  Google Scholar 

  10. Satoh, T., Miura, M., Sakai, K., and Yokoyama, Y., Tetrahedron, 2006, vol. 62, p. 4253.

    Article  CAS  Google Scholar 

  11. Inoue, R., Shinokubo, H., and Oshima, K., Tetrahedron Lett., 1996, vol. 37, p. 5377.

    Article  CAS  Google Scholar 

  12. Vu, V.A., Marek, I., Polborn, K., and Knochel, P., Angew. Chem., Int. Ed., 2002, 351; Kopp, F., Sklute, G., Polborn, K., Marek, I., and Knochel, P., Org. Lett., 2005, vol. 7, p. 3789.

    Google Scholar 

  13. Baird, M.S., Nizovtsev, A.V., and Bolesov, I.G., Tetrahedron, 2002, vol. 58, p. 1581.

    Article  CAS  Google Scholar 

  14. Colov’eva, V.A., Berd, M.S., and Bolesov, I.G., Russ. J. Org. Chem., 2005, vol. 41, p. 1423.

    Google Scholar 

  15. Salaun, J., Russ. J. Org. Chem., 1997, vol. 33, p. 806.

    Google Scholar 

  16. Sheshenev, A.E., Berd, M.S., and Bolesov, I.G., Russ. J. Org. Chem., 2005, vol. 41, p. 1635.

    Google Scholar 

  17. Nizovtsev, A.V., Cand. Sci. (Chem.) Dissertation, Moscow, 2002, p. 136.

    Google Scholar 

  18. Tverezovskii, V.V., Cand. Sci. (Chem.) Dissertation, Moscow., 1999, p. 109.

    Google Scholar 

  19. Gunther, H., NMR Spectroscopy: an Introduction, Chichester: Wiley, 1980.

    Google Scholar 

  20. Stein, C.A., Morton, T.H., Tetrahedron Lett., 1973, vol. 49, p. 4933.

    Article  Google Scholar 

  21. Al Dulayyumi, J.R., Baird, M.S., Bolesov, I.G., Nizovtsev, A.V., and Tverezovsky, V.V., J. Chem. Soc., Perkin Trans., 2000, p. 1603.

    Google Scholar 

  22. Uhlig, W., J. Organometal. Chem., 1994, vol. 469, p. 129.

    Article  Google Scholar 

  23. Toney, J. Stucky, G.D., J. Organometal. Chem., 1971, vol. 28, p. 5.

    Article  Google Scholar 

  24. Seebach, D., J. Organometal. Chem., 1985, vol. 285, p. 1.

    Article  CAS  Google Scholar 

  25. Ioffe, S.T. and Necmeyanov, A.N., Metody elementoorganicheskoi khimii (Methods of Organoelemetal Chemistry), Moscow: Izd. ASSM, 1963; March, J., Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, New York: J. Wiley & Sons, Inc., 1985, p. 158.

    Google Scholar 

  26. Richey, H.G. Jr., Grignard Reagents New Development, Chichester: J. Willey & Sons, Ltd, 2000.

    Google Scholar 

  27. Sydnes, L.K. and Skare, S., Can. J. Chem., 1984, vol. 62, p. 2073.

    Article  CAS  Google Scholar 

  28. Perrin, D.D., Armarego, W.L.F., and Perrin, D.R., Purification of Laboratory Chemicals, 3rd ed., Oxford: Pergamon, Press, 1988, p. 115.

    Google Scholar 

  29. Latypova, M.M., Katerinich, L.V., Baranova, I.N., Plemenkov, V.V., and Bolesov, I.G., Russ. J. Org. Chem., 1982, vol. 18, p. 2552.

    CAS  Google Scholar 

  30. Talalaeva, T.V. and Kocheshkov, K.A., Metody elementoorganicheskoi khimii (Methods of Organoelemental Chemistry), Moscow: Nauka, 1971.

    Google Scholar 

  31. Furuhata, A. and Matsui, M., Agric. Biol. Chem., 1987, vol. 51, p. 1185.

    Article  CAS  Google Scholar 

  32. Makosza, M. and Fedorynski, M. Synth. Commun., 1973, vol. 3, p. 305.

    Article  CAS  Google Scholar 

  33. Wang, M.-X., Feng, G.-Q., and Zheng, Q.-Y., Tetrahedron, Asymmetry, 2004, vol. 15, p. 347.

    Article  CAS  Google Scholar 

  34. Sydnes, L.K. and Scattebol, L., Helv. Chim. Acta, 1975, vol. 58, p. 2061.

    Article  CAS  Google Scholar 

  35. Sydnes, L.K. and Skare, S., Acta Chem. Scand. B, 1984, vol. 41, p. 2073.

    Google Scholar 

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Authors and Affiliations

  1. Lomonosov Moscow State University, Moscow, 119992, Russia

    I. G. Bolesov & V. A. Solov’eva

  2. Department of Chemistry, University of Wales Bangor, LL 57 2 UW, Gwynedd, UK

    M. S. Baird

Authors
  1. I. G. Bolesov
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  2. V. A. Solov’eva
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  3. M. S. Baird
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Corresponding author

Correspondence to V. A. Solov’eva.

Additional information

Original English Text © I.G. Bolesov, V.A. Solov’eva, M.S. Baird, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 11, pp. 1604–1616.

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Bolesov, I.G., Solov’eva, V.A. & Baird, M.S. Functionalized α-bromocyclopropylmagnesium bromides: Generation and some reactions. Russ J Org Chem 49, 1580–1593 (2013). https://doi.org/10.1134/S1070428013110043

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  • DOI: https://doi.org/10.1134/S1070428013110043

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