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Baeyer–Villiger Oxidations with Hydrogen Peroxide in Fluorinated Alcohols: Lactone Formation by a Nonclassical Mechanism
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2002
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Chemical EngineeringEngineeringCatalytic SynthesisFluorous SynthesisOrganic ChemistryOrganometallic CatalysisCatalysisSynthetic ChemistryChemistryBaeyer–villiger OxidationsConventional SolventsHeterocycle ChemistryDeoxygenationHydrogen PeroxideCyclohexanone ReactBiomolecular EngineeringFluorinated Alcohols
What a difference the solvent makes! Unlike in conventional solvents, nonstrained ketones such as cyclohexanone react smoothly with hydrogen peroxide in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) to give lactones. The reaction proceeds via an isolatable spiro-bisperoxide, which undergoes a highly exothermic acid-catalyzed rearrangement to two equivalents of lactone (see Equation and IR thermogram). Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2002/z19329_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.