Trifluoroperacetic Acid. Oxidation of Aromatic Rings

Article abstract of DOI:10.1021/jo01302a026

Trifluoroperacetic acid is an oxidizing reagent capable of converting alkylbenzenes to the corresponding aliphatic carboxylic acids.No trace of aromatic carboxylic acid is ever observed.Aromatic heterocyclic compounds do not behave like their hydrocarbon analogues.Quinoline and pyridine are oxidized to the corresponding N-oxides, and dibenzothiophene is oxidized to the sulfone.No destruction of the ring is found in these latter three cases.The reaction mixture of hydrogen peroxide and trifluoroacetic acid undergoes a decomposition reaction to form carbon dioxide and fluoroform.The rate of this decomposition is slow compared to the oxidation so that ist does not interfere with the primary reaction process.However, attempts to quantify the amount of aromatic carbons in a compound or mixture of compounds must be done with caution.