OXIDATION OF AROMATIC RINGS
Radical-Cations
Aromatic hydrocarbons are oxidised through loss of an electron from the highest occupied π-molecular orbital. This process generates a π-delocalised radical-cation. The electron transfer process is generally irreversible in acetonitrile under normal conditions because the radical-anion reacts rapidly with extraneous nucleophiles, including residual water. A second irreversible oxidation wave is seen at more positive potentials due to the formation of a transitory dication. Solutions of 9,10-diphenylanthracene radical-cation however can be prepared in acetonitrile using an electrochemical flow cell system and the reaction with water followed by uv-spectroscopy [1]. For some substrates, in ...
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