Synthesis of substituted 1,1′-diaminoferrocenes from cyclo-2-pentene imines |
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Authors: | Katharina R Nikolaides |
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Institution: | Technische Universität München, Department Chemie, Lichtenbergstr. 4, D-85747 Garching, Germany |
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Abstract: | Condensation of anilines and primary aliphatic amines with 3,4-diphenylcyclo-2-pentenone leads to the corresponding diphenylcyclopentene imines in good yields of 72-90%. Deprotonation of these aminocyclopentadiene tautomers and reaction with FeCl2 leads to the synthesis of the respective 1,1′-diamino-3,3′,4,4′-tetraphenylferrocenes. Yields increase from 33% to 65% with a decrease in the steric bulk of the amine substituent. The observation that a successful conversion requires two equivalents of base is conceived on the basis of the discussed reaction mechanism. The molecular structure of 1,1′-dianilino-3,3′,4,4′-tetraphenylferrocene (3a), which was determined by single crystal X-ray analysis reveals a trans coordination of the two amine moieties with respect to the central Cp-Fe-Cp axis of the ferrocenyl backbone. |
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Keywords: | Ferrocene Aminoferrocene Diamines Silylamide route |
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