Oxidation of Sulfur-Containing Compounds with HOF-CH3CN

Shlomo Rozen*, Yifat Bareket

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

87 Scopus citations

Abstract

The HOF-CH3CN complex, easily prepared by passing F2 through aqueous acetonitrile, is an exceptionally efficient oxygen transfer agent. All types of sulfides have been oxidized to sulfones in excellent yields, in a few minutes at room temperature. The reaction proceeds through the formation of sulfoxides which at low temperatures of around -75°C could be isolated in good yields. It was demonstrated through a reaction with thianthrene 5-oxide (20) that HOF·CH3CN is strongly electrophilic in nature. Sulfides with an electron-depleted sulfur atom such as perfluoroalkyl or aryl sulfides, which could not be well oxidized by any other method, were also efficiently converted to the corresponding sulfones in minutes. Thiophenes are generally hard to oxidize to the corresponding S-dioxides since the conditions required by the orthodox oxidants encourage consecutive typical ene and diene reactions. HOF·CH3CN requires short reaction times and low temperatures, thus enabling the isolation of thiophene dioxides, some of which could not be made by any other way. It seems that apart from unprotected amines, other functional groups such as aromatic rings, ketones, hydroxyls, and ethers do not interfere, since the sulfur atom reacts considerably faster.

Original languageEnglish
Pages (from-to)1457-1462
Number of pages6
JournalJournal of Organic Chemistry
Volume62
Issue number5
DOIs
StatePublished - 1997

Fingerprint

Dive into the research topics of 'Oxidation of Sulfur-Containing Compounds with HOF-CH3CN'. Together they form a unique fingerprint.

Cite this