Electrolytic partial fluorination of organic compounds. 77. Reactivity of anodically generated benzylic cation intermediates toward fluoride ions in acetonitrile

Toshiki Tajima, Hitoshi Kurihara, Atsushi Nakajima, Toshio Fuchigami

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4 Citations (Scopus)

Abstract

Anodic benzylic fluorination of alkylbenzenes was comparatively studied in MeCN using Et4NF-4HF as a supporting electrolyte and a fluorine source. The anodic benzylic fluorination proceeded except for some cumene derivatives and the yields of fluorinated products greatly depended on the stability of the benzylic cation intermediates. It was found that fluoride ions reacted with more stable benzylic cations preferentially, while acetamidation took place preferentially at less stable benzylic cations.

Original languageEnglish
Pages (from-to)155-160
Number of pages6
JournalJournal of Electroanalytical Chemistry
Volume580
Issue number1
DOIs
Publication statusPublished - 2005 Jun 15

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Keywords

  • Anodic benzylic fluorination
  • Electrochemical fluorination
  • Hammett's substituent constant
  • Stability of benzylic cation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemical Engineering(all)
  • Electrochemistry

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