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Regiochemistry of the addition of mercury salts to bornylene

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Abstract

The dependence of the regiochemistry of the mercuration of bornylene on the nature of the mercurating reagent and on the solvent has been found. The structures of the intermediate and transition state in these reactions have been proposed.

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References

  1. T. G. Traylor,Accouns. Chem. Res., 1969,2, 152.

    Google Scholar 

  2. R. D. Bach and R. F. Richter,J. Am. Chem. Soc., 1972,94, 4747.

    Google Scholar 

  3. V. R. Kartashov, T. N. Sokolova, E. V. Skorobogatova, Yu. K. Grishin, D. V. Bazhenov, V. A. Roznyatovskii, A. S. Koz'min, and N. S. Zefirov,Zh. Org. Khim., 1990,26, 1953 [J. Ogr. Chem. USSR, 1990,26 (Engl. Transl.)].

    Google Scholar 

  4. V. R. Kartashov, E. V. Skorobogatova, T. N. Sokolova, O. V. Vasil'eva, N. V. Malisova, Yu. K. Grishin, D. V. Bazhenov, and N. S. Zefirov,Zh. Org. Khim., 1991,27, 1240 [J. Ogr. Chem. USSR, 1991,27 (Engl. Transl.)].

    Google Scholar 

  5. T. T. Tidwell and T. G. Traylor,J. Org. Chem., 1968,33, 2614.

    Google Scholar 

  6. M. J. S. Dewar and K. M. Merz,Organometallics, 1985,4, 1967.

    Google Scholar 

  7. H. C. Brown and I. H. Kawakami,J. Am. Chem. Soc., 1973,95, 8665.

    Google Scholar 

  8. E. V. Skorobogatova, L. N. Povelikina, and V. R. Kartashov,Zh. Org. Khim., 1980,16, 2318 [J. Ogr. Chem. USSR, 1980,16 (Engl. Transl.)].

    Google Scholar 

  9. J. E. Galle and A. Hassner,J. Am. Chem. Soc., 1972,94, 3930.

    Google Scholar 

  10. G. Bodenhausen and R. Freeman,J. Am. Chem. Soc., 1978,100, 320.

    Google Scholar 

  11. J. K. M. Sanders and J. D. Mersh,Prog. Nucl. Magn. Reson. Spectrosc., 1982,15, 353.

    Google Scholar 

  12. A. P. Marchand and J. E. Rose,J. Am. Chem. Soc., 1968,90, 3724.

    Google Scholar 

  13. J. Paasivirta and P. Ayras,Suomen Kemist., 1970,B43, 82.

    Google Scholar 

  14. V. R. Kartashov, T. N. Sokolova, I. V. Timofeev, Yu. K. Grishin, D. V. Bazhenov, and N. S. Zefirov,Zh. Org. Khim., 1991,27, 2077 [J. Ogr. Chem. USSR, 1991,27 (Engl. Transl.)].

    Google Scholar 

  15. Yu. K. Grishin, D. V. Bazhenov, V. A. Roznyatovskii, M. A. Kazankova, V. R. Kartashov, and Yu, A. Ustynyuk,Metalloorg. Khim., 1988,1, 335 [Organomet. Chem. USSR, 1988,1 (Engl. Transl.)].

    Google Scholar 

  16. M. Barelle and M. Apparu,Tetrahedron, 1977,33, 1309.

    Google Scholar 

  17. V. R. Kartashov, T. N. Sokolova, O. V. Vasil'eva, Yu. K. Grishin, D. V. Bazhenov, and N. S. Zefirov,Metalloorg. Khim., 1993,6, 83 [Organomet. Chem. USSR, 1993,6 (Engl. Transl.)].

    Google Scholar 

  18. V. R. Kartashov, T. N. Sokolova, E. V. Skorobogatova, Yu. K. Grishin, D. V. Bazhenov, and N. S. Zefirov,Zh. Org. Khim., 1991,27, 261 [J. Ogr. Chem. USSR, 1991,27 (Engl. Transl.)].

    Google Scholar 

  19. V. R. Kartashov, E. V. Skorobogatova, N. V. Malisova, Yu. K. Grishin, D. V. Bazhenov, and N. S. Zefirov,Zh. Org. Khim., 1991,27, 2490 [J. Ogr. Chem. USSR, 1991,27 (Engl. Transl.)].

    Google Scholar 

  20. H. C. Brown and J. H. Kawakami,J. Am. Chem. Soc., 1973,95, 8665.

    Google Scholar 

  21. Weigand-Hilgetag,Metody eksperimenta v organicheskoi khimii [Experimental Procedures in Organic Chemistry], Khimiya, Moscow, 1968, 944 (Russ. Transl.).

    Google Scholar 

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 501–505, March, 1994.

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Sokolova, T.N., Kartashov, V.R., Timofeev, I.V. et al. Regiochemistry of the addition of mercury salts to bornylene. Russ Chem Bull 43, 461–465 (1994). https://doi.org/10.1007/BF01169727

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  • DOI: https://doi.org/10.1007/BF01169727

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