Synthetic methods and reactions. XLVI. Oxidation of organic compounds with uranium hexafluoride in haloalkane solutions

Journal Article · Tue Aug 15 20:00:00 EDT 1978 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00485a024· OSTI ID:6548379

Olah, G A; Welch, J

Uranium hexafluoride was found to be an active, yet selective, oxidizing agent for organic compounds. It is very effective in oxidizing methyl ethers, benzylic bromides, N,N-dimethylalkylamines, hydrazenes, benzylic alcohols, and oximes to carbonyl compounds. Benzyl and benzhydryl ethers were cleaved to the parent alcohols. The intermediate oxonium ions formed in the oxidation of ethers were trapped with dithiols to yield 1,2-dithiolanes and 1,3-dithianes. The stability of the intermediate complexes was demonstrated by trapping experiments with n-butyllithium. Fluorination reactions with UF/sub 6/ were also studied. 13 tables; 43 references.

• Research Organization: Univ. of Southern California, Los Angeles
• OSTI ID: 6548379
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 100:17; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400301 -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
400702* -- Radiochemistry & Nuclear Chemistry-- Properties of Radioactive Materials
ACTINIDE COMPOUNDS
ALCOHOLS
ALDEHYDES
AMINES
AROMATICS
BROMINATED AROMATIC HYDROCARBONS
CARBONYLS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
ETHERS
FLUORIDES
FLUORINATION
FLUORINE COMPOUNDS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED AROMATIC HYDROCARBONS
HALOGENATION
HYDRAZONES
HYDROXY COMPOUNDS
KINETICS
METHYL ETHER
ORGANIC BROMINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXIMES
REACTION KINETICS
TRAPPING
URANIUM COMPOUNDS
URANIUM FLUORIDES
URANIUM HEXAFLUORIDE
YIELDS