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Use of hydrogen fluoride and its complexes with bases for introduction of fluorine atoms into organic molecules

G.G.Furin

Novosibirsk Institute of organic chemistry named after N.N.Vorozhtsov 
Siberian branch of the Academy of Science of Russian Federataion

Fax: +7-3822-344752
e-mail: furin@nioch.nsc.ru

Annotation

The review summarizes and systematizes up-to-date data on fluorinating ability of anhydrous hydrogen fluoride and its complexes with bases of unsaturated organic compounds, alcohols, diazoketones, hydrazones and oximes of ketones, 3,3-dialkyl-1-aryltriazenes, aryldiazosulfides etc.. It contains an analysis of main achievements in use of anhydrous hydrogen fluoride as a fluorinating agent to produce ozone-friendly freons in gas and liquid phases both without catalysts and in the presence of latter. There has been examined factors influencing opening three-membered cycles containing oxygen and nitrogen atoms. The review contains examples of practical application of different groups of fluoroorganic compounds, rational methods of their production and their role in development of modern industry . 

Contents

Introduction. Hydrogen fluoride as a basic stock substance in chemical industry.

1. Fluorination with anhydrous hydrogen fluoride and its complexes with bases of compounds from different classes.

1.1.Hydrofluorination of unsaturated compounds
1.1.1. Influence of anhydrous hydrogen fluoride on unsaturated compounds
1.1.2. Hydrofluorination of unsaturated compounds by hydrogen fluoride complexes with bases
1.1.3. Reactions of anhydrous hydrogen fluoride and its complexes containing bases with acetylene derivatives
1.1.4. Fluorination of alkenes with hydrogen fluoride in the presence of catalysts
1.1.5. Fluorination of unsaturated compounds with hydrogen fluoride in the presence of electrophilic reagents

2. Processes of replacement of functional groups with fluorine atoms.

2.1. Replacement of oxy-group with fluorine under effect of hydrogen fluoride complexes containing bases.
2.2. Reactions with hydroxylamines, hydrazones and oximes of ketones.
2.3. Reactions with diazoketones, 3,3-dialkyl-1-aryltriazenes and aryldiazosulfides.
2.4. Exchange reactions of haloids under effect of hydrogen fluoride in the presence of catalysts

3. Opening nitrogen- and oxygen-containing three-membered heterocycles

3.1.Opening an epoxy ring by anhydrous hydrogen fluoride and its complexes with bases.
3.2. Opening nitrogen-containing three-membered heterocycles.

Conclusion. 

References

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