Elsevier

Electrochimica Acta

Volume 35, Issue 7, July 1990, Pages 1167-1171
Electrochimica Acta

Electroorganic reactions on organic electrodes—XII. Functional group-selective reduction using electrodes coated with LB-films of a quaternary ammonium salt: selective reduction of hydroxyl groups of α-hydroxyaldehydes

https://doi.org/10.1016/0013-4686(90)80034-LGet rights and content

Abstract

Glassy carbon electrodes coated with LB(Langmuir—Blodgett)-films of a dimethyldioctadecylammonium salt were found to reduce selectively the hydroxyl groups of α-hydroxyaldehydes having reducible hydroxyl and formyl groups at the same carbon atoms. Similar selective reduction was also observed at an uncoated glassy carbon electrode in a cathodic solution containing a tetraethylammonium salt as a co-supporting electrolyte in high concentrations such as 500 mM.

Reduction mechanism was also discussed from electrochemical and organic-chemical aspects.

References (63)

  • S. Jaouannet et al.

    J. electrochem. Chem.

    (1980)
  • L. Horner et al.

    Tetrahedron Lett.

    (1968)
  • L. Horner et al.

    Tetrahedron Lett.

    (1971)
  • L. Horner et al.

    Tetrahedron Lett.

    (1973)
  • L. Horner et al.

    Electrochim. Acta

    (1974)
  • R. Hazard et al.

    Tetrahedron Lett.

    (1979)
  • R. Hazard et al.

    Tetrahedron

    (1982)
  • E. Kariv et al.

    Electrochem. Acta

    (1973)
  • J. Hermolin et al.

    J. electroanal. Chem.

    (1976)
  • M. Jubault et al.

    Electrochim. Acta

    (1974)
  • M. Jubault et al.

    Electrochim. Acta

    (1976)
  • M. Jubault et al.

    Electrochim. Acta

    (1980)
  • K. Köster et al.

    J. electroanal. Chem.

    (1982)
  • K. Köster et al.

    J. electroanal. Chem.

    (1983)
  • K. Köster et al.

    J. electroanal. Chem.

    (1983)
  • E. Tronel-Peyroz et al.

    J. electroanal. Chem.

    (1981)
  • J. Berthelot et al.

    Electrochim. Acta

    (1983)
  • S. Letellier

    Electrochim. Acta

    (1980)
  • H. Lund et al.

    Electrochim. Acta

    (1974)
  • T. Nonaka et al.

    Electrochim. Acta

    (1981)
  • M.M. Baizer

    J. electrochem. Soc.

    (1964)
  • W.J.W. van Tilborg et al.

    J. R. Netherlands chem. Soc.

    (1979)
  • R. Hazard et al.

    Nouv. J. Chim.

    (1982)
  • L. Horner
  • J.T. Andersson et al.
  • L. Horner et al.

    Chem.-Ing.-Tech.

    (1972)
  • D. Brown et al.

    Liebigs Ann. Chem.

    (1977)
  • L. Horner et al.

    Liebigs Ann. Chem.

    (1978)
  • L. Horner et al.

    Chem. Ber.

    (1978)
  • L. Horner et al.

    Tetrahedron Lett.

    (1970)
  • L. Horner et al.

    Liebigs Ann. Chem.

    (1977)
  • Cited by (7)

    View all citing articles on Scopus
    View full text