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Stable dialkyl ether/poly(hydrogen fluoride) complexes: dimethyl ether/poly(hydrogen fluoride), a new, convenient,
Imre Bucsi1, Béla Török, Alfonso Iza Marco
1Loker Hydrocarbon Research Institute, Department of Chemistry, University of Southern California, University Park, Los Angeles, CA 90089-1661, USA.
Journal of the American Chemical Society
|June 27, 2002
Summary
Stable dialkyl ether/poly(hydrogen fluoride) complexes were synthesized and characterized. The dimethyl ether/poly(hydrogen fluoride) complex (DME-5 HF) is an effective fluorinating agent for various organic reactions, offering high yields and selectivity.
Area of Science:
- Organic Chemistry
- Fluorination Chemistry
- Computational Chemistry
Background:
- Dialkyl ether/poly(hydrogen fluoride) complexes are of interest for synthetic applications.
- Understanding the structure and reactivity of these complexes is crucial for developing new fluorinating agents.
Purpose of the Study:
- To report the preparation and structural characterization of stable dialkyl ether/poly(hydrogen fluoride) complexes.
- To evaluate the potential of these complexes as novel fluorinating agents in organic synthesis.
Main Methods:
- Synthesis and characterization using NMR spectroscopy ((1)H, (13)C, (19)F).
- Density Functional Theory (DFT) based theoretical calculations for structural elucidation.
- Application in various fluorination reactions including hydrofluorination, bromofluorination, and alcohol fluorination.
Main Results:
- Stable dialkyl ether/poly(hydrogen fluoride) complexes were successfully prepared.
- DFT calculations and NMR data confirmed a cyclic poly(hydrogen fluoride) bridged structure for dimethyl ether/poly(hydrogen fluoride) (DMEPHF).
- The DME-5 HF complex demonstrated excellent efficiency as a fluorinating agent, yielding good to excellent results with high selectivity in various reactions.
Conclusions:
- Dialkyl ether/poly(hydrogen fluoride) complexes, including homologous systems (R = Et, nPr), are stable and viable for fluorination.
- DME-5 HF is a convenient and effective new fluorinating agent with easy workup procedures.
- This study expands the toolkit for selective fluorination in organic chemistry.
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