Über die Synthese von substituierten 2-Aminopyrrolinen, 2. Mitt. |
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Authors: | W Klötzer |
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Institution: | 1. Institut für Organische und Pharmazeutische Chemie der Universit?t Innsbruck, Innsbruck, ?sterreich
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Abstract: | Geminal dimethyl substituted N-acylaziridines react with diphenylacetonitrite (as anion), the course of the reaction depending on the nature of the acyl group. N-carbethoxy-2.2-dimethylaziridine undergoes abnormal aziridine ring opening at the gem.-substituted C atom and migration of the carbethoxy group accompanied by 5-membered ring closure to yield as major product N-2-carbethoxylamino-3.3-diphenyl-4.4-dimethylpyrroline-1 (1). In contrast, N-tosyl-2.2-dimethylaziridine undergoes normal ring opening at the less substituted C-atom with retention of the tosyl group on the original N-atom to form N-1-tosyl-2-imino-3.3-diphenyl-5.5-dimethylpyrrolidine (10). Deacylation of the N-carbethoxy- and N-tosyl derivatives yields the substituted 2-aminopyrrolines3, 9 and11. |
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