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Blockhaus, Tobias; Zott, Fabian L.; Zehetmaier, Peter M.; Klein-Hessling, Christian and Sünkel, Karlheinz (2022): Tricyanated Ferrocenes;Isolation, structure, electrochemistry and DFT calculations. In: Zeitschrift für Anorganische und Allgemeine Chemie, Vol. 649, No. 1 [PDF, 949kB]


1,2,3- Tricyanoferrocene and 1,3-dibromo-2,4,5-tricyanoferrocene have been synthesized via metallation and usage of dimethylmalononitrile (DMMN) as cyanating agent. They are the first compounds where three nitrile functions could be introduced into the ferrocene sceleton. Further studies on the electrophilic cyanation of lithiated haloferrocenes [Fe(C5HmX4-mLi)(C5H5)] (X=Cl, Br;m=0-3) show the formation of complex mixtures of cyano-halo-ferrocenes [Fe{C5HmX5-m-n(CN)(n)}(C5H5)] (m=0-3, n=0-3) most likely induced by halogen-dance reactions. The molecular and crystal structures of [Fe{C5H2(CN)(3)}(C5H5)] and [Fe(C5Cl4CN)(C5H5)] are discussed. Cyclic voltametric studies of both tricyanoferrocenes show irreversible oxidations at very high potentials (E-onset approximate to 845 mV and 945 mV, respectively, vs FcH/FcH(+)).

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