title: Generation of Magnesium Pentafluoropropen-2-olate from Hexafluoroisopropanol and Synthesis of 2,2,4,4,4-Pentafluoro-3,3-dihydroxyketones.
abstract: 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 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.
authors.affiliation: Department of BioMolecular Sciences, University of Mississippi , University, Mississippi 38677, United States.
authors.forename: Robert A
authors.initials: RA
authors.lastname: Hazlitt
authors.affiliation: Department of BioMolecular Sciences, University of Mississippi , University, Mississippi 38677, United States.
authors.forename: Que-Lynn
authors.initials: QL
authors.lastname: Tran
authors.affiliation: Department of BioMolecular Sciences, University of Mississippi , University, Mississippi 38677, United States.
authors.forename: Munia F
authors.initials: MF
authors.lastname: Sowaileh
authors.affiliation: Department of BioMolecular Sciences, University of Mississippi , University, Mississippi 38677, United States.
authors.forename: David A
authors.identifier: 0000-0002-5434-1690
authors.initials: DA
authors.lastname: Colby
mesh_terms: D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*
chemical_list: D006845:Hydrocarbons, Fluorinated; D009942:Organometallic Compounds; D020005:Propanols; C001337:hexafluoroisopropanol