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Synthetic Methods and Reactions. 46.1 Oxidation of Organic Compounds with Uranium Hexafluoride in Haloalkane Solutions

  • University of Southern California

Research output: Contribution to journalArticlepeer-review

47 Scopus citations

Abstract

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, hydrazones, 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 UF6 were also studied.

Original languageEnglish
Pages (from-to)5396-5402
Number of pages7
JournalJournal of the American Chemical Society
Volume100
Issue number17
DOIs
StatePublished - 1978

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