Stable dialkyl ether/poly(hydrogen fluoride) complexes: Dimethyl ether/poly(hydrogen fluoride), a new, convenient, and effective fluorinating agent

Imre Bucsi, Béla Török, Alfonso Iza Marco, Golam Rasul, G. K.Surya Prakash, George A. Olah

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

The preparation, 1H, 13C, and 19F NMR structural characterization as well as with DFT-based theoretical calculations of stable dialkyl ether/poly(hydrogen fluoride) complexes are reported. Dimethyl ether/poly(hydrogen fluoride) (DMEPHF), are stable complexes of particular interest and use. The DFT calculations, that are in agreement with NMR data, suggest a cyclic poly(hydrogen fluoride) bridged structure for DMEPHF. The complex, DME-5 HF was found to be a convenient and effective new fluorinating agent with the ease. of workup and applied to several fluorination reactions, such as the hydrofluorination and bromofluorination of alkenes, and fluorination of alcohols giving good to excellent yield with high selectivity. Homologous dialkyl ether/poly(hydrogen fluoride) (R2O/[HF]n R = Et, nPr) systems are also stable and suitable for fluorination reactions.

Original languageEnglish
Pages (from-to)7728-7736
Number of pages9
JournalJournal of the American Chemical Society
Volume124
Issue number26
DOIs
Publication statusPublished - Jul 3 2002

ASJC Scopus subject areas

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

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