N-arylammonio- and N-pyridinium-substituted derivatives of dodecahydro-closo-dodecaborate(2-) |
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| Authors: | Andrea Vöge Enno Lork Detlef Gabel |
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| Institution: | a Department of Chemistry, University of Bremen, Leobener Str. NW2 C3020, D-28357 Bremen, Germany
b Department of Chemistry, Technical University of Istanbul, Maslak 34469, Istanbul, Turkey |
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| Abstract: | We report two methods for preparing N-arylammonio, N-pyridyl and N-arylamino dodecaborates: heating of the tetrabutylammonium salt of dodecahydro-closo-dodecaborate(2-) with aryl and pyridyl amines, or nucleophilic attack of closo-B12H11NH2]2− on a strongly deactivated aromatic system. With aryl amines we obtained 1-closo-B12H11N(R1)2C6H5]− (R1 = H, CH3). With 4-(dimethylamino)pyridine, 1-closo-(B12H11NC5H4)-4-N(CH3)2]−, with a bond between the boron and the pyridinium nitrogen, was obtained. A presumable mechanism for this kind of reactions is reported. By nucleophilic substitution, two products, 1-closo-(B12H11NHC6H3)-3,4-(CN)2]2− and 1-closo-(B12H11NHC6H2)-2-(NO2)-4,5-(CN)2]2−, were formed with 4-nitrophthalonitrile and 1-chloro-2,4-dinitrobenzene gave 1-closo-(B12H11NHC6H3)-2,4-(NO2)2]2−. For 1-closo-B12H11N(CH3)2C6H5]− and 1-closo-(B12H11NHC6H3)-2,4-(NO2)2]2− single crystal X-ray structures were obtained. |
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| Keywords: | Aromatic substitution B-pyridinium Hofmann elimination Hydroamination Dodecahydro-closo-dodecaborate |
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