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Lithiacarboranes and 1,2,4-triazine 4-oxides: S N H reactions and ring transformations

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Abstract

The reactions of 1-lithia-1,2- or 1,7-dicarba-closo-dodecaborane with 1,2,4-triazine 4-oxides can follow two competitive pathways: deoxygenative nucleophilic substitution of hydrogen to form 1-(1,2,4-triazin-5-yl)-1,2- or 1,7-dicarba-closo-dodecaboranes and the transformation of the 1,2,4-triazine ring into the triazoline ring giving rise to 1-(2-acetyl-1-aroyl-3-aryl-1,2,4-triazolin-5-yl)-1,2-dicarba-closo-dodecaboranes. Introduction of the electron-withdrawing triazine ring into the carborane cage substantially facilitates deboronation to give 1-(1,2,4-triazin-5-yl)-1,2-1,7-dicarba-nido-undecaboranes.

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Authors and Affiliations

  1. Urals State Technical University, 19 ul. Mira, 620002 Ekaterinburg, Russian Federation, Russia

    O. N. Chupakhin, A. M. Prokhorov, D. N. Kozhevnikov & V. L. Rusinov

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation, Russia

    I. A. Glukhov, Z. A. Starikova, V. A. Ol"shevskaya, V. N. Kalinin & M. Yu. Antipin

Authors
  1. O. N. Chupakhin
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  2. A. M. Prokhorov
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  3. D. N. Kozhevnikov
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  4. V. L. Rusinov
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  5. I. A. Glukhov
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  6. Z. A. Starikova
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  7. V. A. Ol"shevskaya
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  8. V. N. Kalinin
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  9. M. Yu. Antipin
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Chupakhin, O.N., Prokhorov, A.M., Kozhevnikov, D.N. et al. Lithiacarboranes and 1,2,4-triazine 4-oxides: S N H reactions and ring transformations. Russian Chemical Bulletin 53, 1223–1231 (2004). https://doi.org/10.1023/B:RUCB.0000042277.99035.a8

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  • DOI: https://doi.org/10.1023/B:RUCB.0000042277.99035.a8

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