Preparation of first examples of RFCCIF4 molecules. A study of the fluorination of selected 1-iodoalk-1-ynes with xenon difluoride/boron trifluoride
| Autor: | Vadim V. Bardin, Hermann-Josef Frohn |
|---|---|
| Rok vydání: | 2013 |
| Předmět: |
Organic Chemistry
Xenon difluoride Chemie chemistry.chemical_element Nuclear magnetic resonance spectroscopy Triple bond Biochemistry Medicinal chemistry Compound C-6 Inorganic Chemistry chemistry.chemical_compound chemistry Fluorine Environmental Chemistry Molecule Reactivity (chemistry) Physical and Theoretical Chemistry Boron trifluoride |
| Zdroj: | Journal of Fluorine Chemistry. 146:98-104 |
| ISSN: | 0022-1139 |
| DOI: | 10.1016/j.jfluchem.2013.01.006 |
| Popis: | First examples of alk-1-yn-1-yliodine(V) molecules, CF 3 C CIF 4 and C 6 F 13 C CIF 4 , were prepared by fluorination of the corresponding 1-iodoperfluoroalk-1-ynes with XeF 2 in 1,1,1,3,3-pentafluorobutane (PFB) in the presence of BF 3 . The reaction of 1-iodo-2-(4-heptafluorotolyl)ethyne, 4-CF 3 C 6 F 4 C CI, with XeF 2 (1.5 equiv) and BF 3 resulted in a mixture of 4-CF 3 C 6 F 4 C CIF 2 (main product), 4-CF 3 C 6 F 4 C CIF 4 , and trans -(4-CF 3 C 6 F 4 )CF CFI, whereas under the action of 3 equiv of XeF 2 /BF 3 a complex mixture of polyfluoroorganics and IF 5 resulted. Non-fluorinated C 4 H 9 C CI reacted with XeF 2 /BF 3 preferentially under fluorine addition across the triple bond and gave mainly C 4 H 9 CF 2 CF 2 I. The differing reactivity of C n F 2 n +1 C CI and C 4 H 9 C CI is in accordance with the experimentally proved different reactivity of the triple bond in C 6 F 13 C CH and C 4 H 9 C CH toward XeF 2 /BF 3 in PFB. Compound C 6 F 13 C CH was inert whereas C 4 H 9 C CH was converted into C 4 H 9 CF 2 CF 2 H (main product) under the same conditions. |
| Databáze: | OpenAIRE |
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