Coupling routes to hexafluoro-1,3-butadiene, substituted-1,3-fluorine-containing butadienes and fluorinated polyenes
| Autor: | Donald J. Burton, Steven W. Hansen, Kathryn J. MacNeil, Charles R. Davis, Ling Xue, P. A. Morken |
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| Rok vydání: | 2008 |
| Předmět: |
chemistry.chemical_classification
Chemistry Organic Chemistry Iodide 1 3-Butadiene Fluorine containing Photochemistry Biochemistry Catalysis Inorganic Chemistry Coupling (electronics) chemistry.chemical_compound Stereospecificity Reagent Polymer chemistry Environmental Chemistry Physical and Theoretical Chemistry |
| Zdroj: | Journal of Fluorine Chemistry. 129:435-442 |
| ISSN: | 0022-1139 |
| DOI: | 10.1016/j.jfluchem.2007.11.004 |
| Popis: | Hexafluoro-1,3-butadiene was readily prepared via a variety of self-coupling processes, such as Cu(0) mediated self-coupling of iodotrifluoroethene, Pd(0) catalyzed coupling of iodotrifluoroethene with the trifluorovinylzinc reagent, and CuBr 2 mediated coupling of the trifluorovinylzinc reagent. Perfluoro-2,3-dimethyl-1,3-butadiene was readily synthesized by the reaction of pentafluoropropenyl-2-zinc reagent with either CuBr 2 or FeCl 3 . Alternatively, perfluoro-2,3-dimethyl-1,3-butadiene was prepared by oxidation of the pentafluoropropenyl-2-copper reagent with dioxygen. Cu(0) mediated coupling of an ( E )-substituted α,β-difluoro-β-iodostyrene provided the first useful route to a ( Z )( Z )-1,4-diaryl-1,3-tetrafluorobutadiene. Extension of the Cu(0) mediated coupling methodology to a perfluorodienyl iodide demonstrated a useful stereospecific route to perfluoropolyenes. |
| Databáze: | OpenAIRE |
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