Anhydrous tetrabutylammonium fluoride

Haoran Sun, Stephen G. DiMagno

Research output: Contribution to journalArticle

253 Citations (Scopus)

Abstract

Tetrabutylammonium fluoride (TBAF) is prepared at low temperature by nucleophilic aromatic substitution of hexafluorobenzene with tetrabutylammonium cyanide. Adventitious water is scavenged during this synthesis by the generated hexacyanobenzene, which readily adds water under basic conditions. Contrary to expectations, TBAF is stable to Hofmann elimination in polar aprotic solvents under anhydrous conditions. Added hydroxylic solvents are shown to catalyze the decomposition of TBAF and to catalyze proton exchange with DMSO. The synthetic utility of this salt is described briefly.

Original languageEnglish (US)
Pages (from-to)2050-2051
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number7
DOIs
StatePublished - Feb 23 2005

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Cyanides
Water
Ion exchange
Protons
Substitution reactions
Salts
Decomposition
Dimethyl Sulfoxide
Temperature
tetrabutylammonium
hexafluorobenzene

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Anhydrous tetrabutylammonium fluoride. / Sun, Haoran; DiMagno, Stephen G.

In: Journal of the American Chemical Society, Vol. 127, No. 7, 23.02.2005, p. 2050-2051.

Research output: Contribution to journalArticle

Sun, Haoran ; DiMagno, Stephen G. / Anhydrous tetrabutylammonium fluoride. In: Journal of the American Chemical Society. 2005 ; Vol. 127, No. 7. pp. 2050-2051.
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