Abstract
Anodic oxidation of ferrocenes bearing an electron-withdrawing substituent with a H-atom in the α-position (ferrocenylacetic acid 1a, ferrocenylacetonitrile 2a) has been investigated by cyclic voltammetry and by macroscale electrolysis in a flow cell fitted with a porous graphite felt anode. Oxidation of ferrocenes ( 1a, 2a) into their ferrocenium cations ( 1a +, 2a +) increases the acidity of the H-atom in the α-position to the cyclopentadienyl ligand. The deprotonation is favoured by a basic medium to give a radical ( 1b, 2b). According to the substrate, the radical can be oxidised ( 1b) or can dimerise ( 2b). Exhaustive electrolysis of 1a leads to ferrocenecarboxaldehyde after multi-step reactions (redox reactions and nucleophilic attack by H 2O). Electrolysis of 2a affords a dimer which was further oxidised into 1,2-diferrocenyl-1,2-dicyano ethylene.
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