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Nucleophilic substitution in closo-decaborate [B10H10]2− in the presence of carbocations

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Abstract

Nucleophilic substitution at the exo-polyhedral boron atoms of claso-decaborate [B10H10]2- in the presence of carbocations, which were generated in situ from various halocarbons (triphe-nylmethyl chloride, 1-bromoadamantan, n-butyl bromide), was studied. The reactions carried out in nucleophilic solvents (cyclic ethers and thioethers, N,N-disubstituted amides, and car-boxylic acids) and in the presence of halocarbons afforded mono-and disubstituted compounds with the exo-polyhedral B—O and B—S bonds, which contained a molecule of the solvent as substituent. The structures of the compounds synthesized were confirmed by the IR, mass, and 1H, 11B, and 13C NMR spectra.

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References

  1. M. F. Hawthorne, Angew. Chem., Int. Ed., 1993, 32, 930.

    Google Scholar 

  2. A. H. Soloway, W. Tjarks, B. A. Barnum, F.-G. Rong, R. F. Barth, I. M. Codogni, J. G. Wilson, Chem. Rev., 1998, 98, 1515.

    Article  CAS  Google Scholar 

  3. V. A. Popov, K. Yu. Zhizhin, E. A. Malinina, V. M. Retivov, K. P. Staudhammer, N. T. Kuznesov, Mat. Sci. Forum, 2008, 587, 197.

    Article  Google Scholar 

  4. J. Plesek, Chem. Rev., 1992, 92, 269.

    Article  CAS  Google Scholar 

  5. R. Bernard, D. Cornu, B. Grüner, J.-F. Dozol, P. Miele, B. Bonnetot, J. Organomet. Chem., 2002, 657, 83

    Article  CAS  Google Scholar 

  6. T. Jelinek, B. Štibr, F. Mareš, J. Plešek, S. Heřmánek, Polyhedron, 1987, 6, 1737.

    Article  CAS  Google Scholar 

  7. D. Dou, I. J. Mavunkal, J. A. K. Bauer, C. B. Knober, M. F. Hawthorne, Inorg. Chem., 1994, 33, 6432.

    Article  CAS  Google Scholar 

  8. K. Yu. Zhizhin, V. N. Mustyatsa, E. A. Malinina, N. A. Votinova, E. Yu. Matveev, L. V. Goeva, I. N. Polyakova, N. T. Kuznetzov, Zh. Neorg. Khim., 2004, 49, 221 [Russ. J. Inorg. Chem. (Engl. Transl.), 2004, 49, 180].

    CAS  Google Scholar 

  9. K. Yu. Zhizhin, V. N. Mustyatsa, E. A. Malinina, I. N. Polyakova, N. T. Kuznetzov, Zh. Neorg. Khim., 2005, 50, 33 [Russ. J. Inorg. Chem. (Engl. Transl.), 2005, 50, 29].

    CAS  Google Scholar 

  10. W. Preetz, R. Bismarck, J. Organomet. Chem., 1991, 411, 25.

    Article  CAS  Google Scholar 

  11. I. B. Sivaev, A. A. Semioshkin, B. Brellochs, S. Sjoberg, V. I. Bregadze, Polyhedron, 2000, 19, 627.

    Article  CAS  Google Scholar 

  12. T. Peymann, K. Kück, D. Gabel, Inorg. Chem., 1997, 36, 5138.

    Article  CAS  Google Scholar 

  13. D. Gabel, S. Mai, O. Perleberg, J. Organomet. Chem., 1999, 581, 45.

    Article  CAS  Google Scholar 

  14. B. Brellochs, A. A. Semioshkin, Izv. Akad. Nauk, Ser. Khim., 1995, 421 [Russ. Chem. Bull. (Engl. Transl.), 1995, 44, 406].

  15. V. N. Mustyatsa, N. A. Votinova, K. A. Solntsev, N. T. Kuznetzov, Dokl. Akad. Nauk SSSR, 1988, 301, 1396 [Dokl. Chem. (Engl. Transl.), 1988, 301].

    CAS  Google Scholar 

  16. E. A. Malinina, K. Yu. Zhizhin, I. N. Polyakova, M. V. Lisovskiy, N. T. Kuznetzov, Zh. Neorg. Khim., 2002, 47, 1279 [Russ. J. Inorg. Chem. (Engl. Transl.), 2002, 47, 1158].

    Google Scholar 

  17. V. V. Drozdova, K. Yu. Zhizhin, E. A. Malinina, I. N. Polyakova, N. T. Kuznetzov, Zh. Neorg. Khim., 2007, 52, 1072 [Russ. J. Inorg. Chem. (Engl. Transl.), 2007, 52, 996].

    CAS  Google Scholar 

  18. K. Yu. Zhizhin, V. N. Mustyatsa, E. A. Malinina, N. A. Votinova, E. Yu. Matveev, L. V. Goeva, I. N. Polyakova, N. T. Kuznetzov, Zh. Neorg. Khim., 2004, 49, 221 [Russ. J. Inorg. Chem. (Engl. Transl.), 2004, 49, 180].

    CAS  Google Scholar 

  19. H. C. Miller, N. E. Miller, E. L. Muetterties, J. Am. Chem. Soc., 1963, 85, 3885.

    Article  CAS  Google Scholar 

  20. E. L. Muetterties, J. H. Baltnis, Y. T. Chia, W. N. Knoth, H. C. Miller, Inorg. Chem., 1964, 3, 444.

    Article  CAS  Google Scholar 

  21. H. Becker, G. Domshke, E. Fanghanel, Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin, 1990.

    Google Scholar 

  22. L. I. Ochertyanova, V. N. Mustyatsa, K. Yu. Zhizhin, O. N. Belousova, N. T. Kuznetzov, Neorg. materialy, 2004, 40, 188 [Inorg. Mater. (Engl. Transl.), 2004, 40, 144].

    Article  Google Scholar 

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Authors and Affiliations

  1. N. S. Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences, 31 Leninskyprosp., 119991, Moscow, Russian Federation

    V. M. Retivov, E. Yu. Matveev, M. V. Lisovskiy, G. A. Razgonyaeva, L. I. Ochertyanova, K. Yu. Zhizhin & N. T. Kuznetsov

  2. M. V. Lomonosov Moscow State Academy of Fine Chemical Technology, 86 prosp. Vernadskogo, 119571, Moscow, Russian Federation

    V. M. Retivov, E. Yu. Matveev, K. Yu. Zhizhin & N. T. Kuznetsov

Authors
  1. V. M. Retivov
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  2. E. Yu. Matveev
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  3. M. V. Lisovskiy
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  4. G. A. Razgonyaeva
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  5. L. I. Ochertyanova
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  6. K. Yu. Zhizhin
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  7. N. T. Kuznetsov
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Correspondence to K. Yu. Zhizhin.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 538–543, March, 2010.

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Retivov, V.M., Matveev, E.Y., Lisovskiy, M.V. et al. Nucleophilic substitution in closo-decaborate [B10H10]2− in the presence of carbocations. Russ Chem Bull 59, 550–555 (2010). https://doi.org/10.1007/s11172-010-0123-2

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  • DOI: https://doi.org/10.1007/s11172-010-0123-2

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