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Useful Electro-Oxidative Conversions of Aromatic Compounds

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

Abstract

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.

Keywords

Aromatic Aldehyde Constant Current Substituent Effect Anodic Regeneration Graphite Anode 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

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    BASF AG-GE patent 2848397 (1980); BASF AG-GE patent 2855508 (1980); BASF AG-GE patent 2935398 (1981);Google Scholar
  2. (2).
    I. Fussing, M. Güllü, O. Hammerich, A. Hussain, M.F. Nielsen and J.H.P. Utley, J. Chem. Soc., Perkin Trans. 2, 1996, 649; O. Hammerich and M.F. Nielsen, Acta Chem. Scand.,in press; J. Heinze, A. Smie, R. Müller, P. Hübler, P. Tschunky and K. Meerholz, Abstract 1272, 192nd ECS Meeting, Paris 1997;Google Scholar
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    U.H. Brinker, M. Tyner III and W.M. Jones, Synthesis, 1975, 671Google Scholar

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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