Lithiacarboranes and 1,2,4-triazine 4-oxides: S N H reactions and ring transformations |
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Authors: | Chupakhin O N Prokhorov A M Kozhevnikov D N Rusinov V L Glukhov I A Starikova Z A Ol"shevskaya V A Kalinin V N Antipin M Yu |
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Institution: | (1) Urals State Technical University, 19 ul. Mira, 620002 Ekaterinburg, Russian Federation, Russia;(2) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation, Russia |
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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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Keywords: | nucleophilic substitution of hydrogen ring transformation 1 2 4-triazine carborane hetarylcarboranes |
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