Acidic hydrolysis of N-acyl-1-substituted 3-amino-1,2-dicarba-closo-dodecaboranes |
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| Authors: | Galina L Levit Alexander M Demin Marina A Ezhikova Valentina A Ol’shevskaya Victor P Krasnov |
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| Institution: | a I.Ya. Postovsky Institute of Organic Synthesis of RAS (Ural Div.), S. Kovalevskoy St., 20, Ekaterinburg, 620219, Russia
b A. N. Nesmeyanov Institute of Organoelement Compounds of RAS, Vavilova St., 28, Moscow, 119991, Russia |
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| Abstract: | Acidic hydrolysis of N-acyl 1-methyl- and 1-phenyl-3-amino-1,2-dicarba-closo-dodecaboranes has been studied. It has been shown that acidic hydrolysis of diastereomeric amides of 1-methyl-3-amino-1,2-dicarba-closo-dodecaborane results in the partial racemization of the target 3-amino-1-methylcarborane. Under the similar conditions, the hydrolysis of N-acyl-3-amino-1-phenyl-1,2-dicarba-closo-dodecaboranes resulted in amide bond cleavage accompanied by simultaneous deboronation with the removal of boron atom at position 6 of carborane cage and formation of 7,8-dicarba-nido-undecaborane derivative according to 11B and 1H NMR spectroscopy. |
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| Keywords: | 3-Amino-1 2-dicarba-closo-dodecaboranes Amides Acidic hydrolysis Racemization Deboronation NMR spectroscopy |
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