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

The preparation, (1)H, (13)C, and (19)F 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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2002-07, Vol.124 (26), p.7728-7736
Main Authors: BUCSI, Imre, TÖRÖK, Béla, IZA MARCO, Alfonso, RASUL, Golam, SURYA PRAKASH, G. K, OLAH, George A
Format: Article
Language:English
Subjects:
Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
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Summary:The preparation, (1)H, (13)C, and (19)F 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) (R(2)O/[HF](n,), R = Et, nPr) systems are also stable and suitable for fluorination reactions.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0124109