Useful Electro-Oxidative Conversions of Aromatic Compounds

  • James H. P. Utley
  • Gregor G. Rozenberg
Conference paper


Conditions for the direct and indirect side-chain oxidation of methylnaphthalenes were explored, together with substituent effects likely to influence the acidity of their radical-cations. That substituent effects alter the electron demand at side-chain positions was shown using chemical shifts (13C) at the benzylic carbons of 2-benzylnaphthalenes substituted at the para position of the benzyl group. However, the reactivity of 2-methylnaphthalenes in direct anodic oxidation ranges from exclusive dimerisation to exclusive nuclear substitution with negligible attack at the methyl group.

In contrast DDQ is an effective side-chain oxidant for electron-rich 2-methylnaphthalenes. An indirect method was devised in which non-stoichiometric amounts of DDQ are used with continuous anodic regeneration in an undivided cell and at constant current.


Aromatic Aldehyde Constant Current Substituent Effect Anodic Regeneration Graphite Anode 
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Copyright information

© Springer Japan 1998

Authors and Affiliations

  • James H. P. Utley
    • 1
  • Gregor G. Rozenberg
    • 1
  1. 1.Department of ChemistryQueen Mary and Westfield College (University of London)LondonUK

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