Abstract
A direct reaction between ferrocene (FcH) and tetracyanoethylene (TCNE) in various solvents and within a wide range of temperatures has been investigated in order to optimize the preparation of tricyanovinylferrocene. Under optimized reaction conditions, tricyanovinylferrocene was prepared in ∼26% yield along with cyanoferrocene as a major reaction product in the reaction between 1 equiv of FcH and 2 equiv of TCNE for 10 min in sulfolane at 110 °C. It was proposed that the reaction proceeds via a single-electron-transfer step, which results in the formation of a spectroscopically detected [FcH]•+[TCNE]•- intermediate followed by homolytic cleavage of the C−CN bond. The possible phase transition in tricyanovinylferrocene has been tested by X-ray crystallography at 173 and 293 K. The prominent visible band observed in the UV−vis spectrum of tricyanovinylferrocene has been unambiguously assigned to a metal-to-ligand charge-transfer transition on the basis of experimental and theoretical (TDDFT) data, while i...
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