Electroorganic reactions. Part 57.† DDQ mediated anodic oxidation of 2-methyl- and 2-benzylnaphthalenes

Utley, J.H.P.; Rozenberg, G.G.
June 2003
Journal of Applied Electrochemistry;Jun2003, Vol. 33 Issue 6, p525
Academic Journal
Electron-rich 2-methyl and 2-benzylnaphthalenes are efficiently converted into the corresponding carboxaldehyde or ketone by mediated electrolysis in the presence of about 25 mol % of DDQ. The reaction conditions are simple (constant current, undivided cell of 500 ml volume, graphite electrodes, aqueous acetic acid at 80 °C) and the construction of a reaction profile (products vs charge) shows the intermediate formation of side-chain acetoxy and hydroxy derivatives and the parallel formation of a byproduct involving side-chain substitution by DDQ.


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