Electric Literature of 1273-94-5, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.1273-94-5, Name is 1,1′-Diacetylferrocene, molecular formula is C14H6FeO2. In a Article£¬once mentioned of 1273-94-5
Formation and structural characterization of amino-substituted [3]ferrocenophanes derived from intramolecular Mannich-type coupling reactions at the metallocene framework
Treatment of lithium(1-dimethylamino-ethenyl)cyclopentadienide (5a) with FeCl2 generated the corresponding substituted ferrocene (2a) that rapidly underwent cyclization in a subsequent Mannich-type condensation reaction to yield the unsaturated dimethylamino-substituted [3]ferrocenophane 3a. The treatment of 1,1?-diacetylferrocene (1) with dimethylamine, diethylamine or piperidine in the presence of TiCl4 resulted in the formation of the analogously structured functionalized [3]ferrocenophanes 3a-3c, respectively, by a related intramolecular enamine-condensation pathway (complexes 3a and 3b were characterized by X-ray diffraction). Catalytic hydrogenation of 3a-c in THF at Pd/C gave the corresponding saturated amino-substituted [3]ferrocenophane systems 6a-c. The catalytic hydrogenation proceeds trans-product selectively with trans-6-cis-6 ratios ranging between ca. 5:1 and 7:1 for these examples (the complexes trans-6a¡¤HCl, trans-6b, and trans-6c were characterized by X-ray crystal structure analysis). Quaternization of 6a by treatment with methyliodide followed by the reaction with pyrrolidine led to amine exchange at the [3]ferrocenophane framework with the formation of 6d. The amine exchange proceeds stereoselectively with a predominant overall retention (the trans-6d-cis-6d ratio obtained is again ca. 7:1). The complex trans-6d was characterized by X-ray diffraction.
Formation and structural characterization of amino-substituted [3]ferrocenophanes derived from intramolecular Mannich-type coupling reactions at the metallocene framework
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Reference£º
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion