Highly fluorinated heterocycles. Part XVIII. 2-Difluoromethyl- and 2-trifluoromethyl- hexa- and penta- fluoro-oxolans
| Autor: | John Colin Tatlow, J. Anthony Smith, James Burdon, Paul L. Coe |
|---|---|
| Rok vydání: | 1991 |
| Předmět: |
chemistry.chemical_classification
Aluminium chloride Trifluoromethyl Aluminium fluoride Double bond Potassium Organic Chemistry chemistry.chemical_element HEXA Biochemistry Medicinal chemistry Cobalt trifluoride Inorganic Chemistry chemistry.chemical_compound chemistry medicine Environmental Chemistry Organic chemistry Physical and Theoretical Chemistry Isomerization medicine.drug |
| Zdroj: | Journal of Fluorine Chemistry. 51:179-196 |
| ISSN: | 0022-1139 |
| DOI: | 10.1016/s0022-1139(00)80289-4 |
| Popis: | 2-Methyltetrahydrofuran with potassium tetrafluorocobaltate(III) at 200 °C gave largely 3H, 4H-2-difluoromethyltrifluoro-3-oxolen. Further fluorination of this by cobalt trifluoride at 120–150 °C afforded many of the stereoisomers expected from saturation of the double bond, and from further replacement of one, and of two hydrogens; viz:- four 3H, 4H-2-difluoromethyl- and two 3H, 4H-2-trifluoromethyl- pentafluoro-oxolans; two 3H- and two 4H- 2- difluoromethylhexafluoro-oxolans; two 3H- and two 4H- 2-trifluoromethylhexafluoro-oxolans. The two trans-3, 4-difluoro-adducts of the starting 3-oxolen were the major individual products, followed by the two cis-analogues, which altogether comprised some 63% of the material isolated. These trans-isomers were interconverted by heated aluminium fluoride, and the 4H/3H-stereoisomer reacted with aluminium chloride by exchanging the α-fluorines for chlorines. |
| Databáze: | OpenAIRE |
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