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Reactions of Electrochemically Generated Alkoxy Phosphonium Ions

  • Hidenobu Ohmori
  • Hatsuo Maeda
  • Sayaka Matsumoto
  • Takashi Koide
  • Toshihide Maki
Conference paper

Abstract

Reactions of alkoxy triphenylphosphonium salts (1), prepared by a simple electrochemical procedure from primary and secondary alcohols, with nucleophiles indicated that a soft nucleophile is apt to attack at the α -carbon to give the corresponding Sn2 product, while a hard one at the phosphorus atom to regenerate the original alcohol. Thermal decomposition of 1 with BF4 - as counter anion has been shown to afford alkyl fluorides. One-pot dehydroxysubstitution reactions at the anomeric carbons of protected sugars has been effected via in situ decomposition of the corresponding electrochemically generated alkoxy phosphonium ions.

Keywords

Secondary Alcohol Tertiary Alcohol Phosphonium Salt Anomeric Carbon Undivided Cell 
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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Copyright information

© Springer Japan 1998

Authors and Affiliations

  • Hidenobu Ohmori
    • 1
  • Hatsuo Maeda
    • 1
  • Sayaka Matsumoto
    • 1
  • Takashi Koide
    • 1
  • Toshihide Maki
    • 2
  1. 1.Faculty of Pharmaceutical SciencesOsaka UniversityOsaka 565Japan
  2. 2.Facult of Pharmaceutical SciencesNagasaki UniversityOsaka 565Japan

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