OXIDATION OF KETONES, ALDEHYDES, AND CARBOXYLIC ACIDS
Oxidation of Ketones
Aliphatic ketones are oxidised in both acetonitrile[1,2] and trifluoracetic acid[3] at potentials less positive than required for the analogous hydrocarbons. The oxidation process is irreversible in both solvents and cyclic voltammetry peak potentials are around 2.7 V vs. sce. Loss of an electron from the carbonyl oxygen lone pair is considered to be the first stage in the reaction. In acetonitrile, two competing processes then ensue. Short chain, α-branched ketones cleave the carbon-carbonyl bond to give the more stable carbocation, which is then quenched by reaction with
acetonitrile and water. The fate of the carbonyl residue has not been clarified. Longer ...
Get Electrochemical Reactions and Mechanisms in Organic Chemistry now with the O’Reilly learning platform.
O’Reilly members experience books, live events, courses curated by job role, and more from O’Reilly and nearly 200 top publishers.
