Generation of Magnesium Pentafluoropropen-2-olate from Hexafluoroisopropanol and Synthesis of 2,2,4,4,4-Pentafluoro-3,3-dihydroxyketones
| Autor: | David A. Colby, Robert A. Hazlitt, Munia F. Sowaileh, Que-Lynn Tran |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Hydrocarbons
Fluorinated Molecular Structure Propanols 010405 organic chemistry Chemistry Magnesium Organic Chemistry Periodinane chemistry.chemical_element 010402 general chemistry 01 natural sciences Article 0104 chemical sciences chemistry.chemical_compound Fragmentation (mass spectrometry) Amide Organometallic Compounds Molecule Organic chemistry Group 2 organometallic chemistry |
| Zdroj: | J Org Chem |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | 2,2,4,4,4-Pentafluoro-3,3-dihydroxyketones are valuable precursors to difluoroenolates, following fragmentation during the release of trifluoroacetate; however, there are few synthetic strategies to prepare this unique class of compound. We have addressed this issue and report a mild, two-step synthesis of 2,2,4,4,4-pentafluoro-3,3-dihydroxyketones from aldehydes. Specifically, aldehydes are treated with pentafluoropropen-2-olate, generated from a new fragmentation of hexafluoroisopropanol with a mixed Mg/Li amide, to give pentafluoroalcohols. A subsequent oxidation with Dess-Martin periodinane provides the targets in good isolated yields. |
| Databáze: | OpenAIRE |
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