Reaction of N-alkoxycarbonylaziridines with nitriles |
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Authors: | T Hiyama H Koide S Fujita H Nozaki |
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Institution: | Department of Industrial Chemistry, Kyoto University, Yoshida, Kyoto, Japan |
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Abstract: | The acid catalysed reaction of acetonitrile or benzonitrile with N-alkoxycarbonylaziridines, 1a and 1b yields the corresponding 1-alkoxycarbonyl-2-imidazolines, 2ax, 2ay, and 2bx. The imidazolines obtained by the reaction of N-ethoxycarbonyl-2,3-tetramethyleneaziridine (1c) with acetonitrileor benzonitrile are labile and are readily hydrolysed to trans-cyclohexane-1,2-diamine derivatives (3cx or 3cy). The nitrile-addition supposedly proceeds SN2 type CN bond cleavage and CN bond formation. |
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