Mild and Selective Oxygenation of Sulfides to Sulfoxides and Sulfones by Perfluoro-cis-2,3-dialkyloxaziridines

Sulfides are oxidized to sulfoxides by stoichiometric amounts of perfluoro-cis-2,3-dialkyloxaziridines 2. The reactions proceed at -40 degrees C with nearly complete selectivity and very good yields. Sulfoxides are also oxidized easily by 2 under mild conditions to corresponding sulfones. The oxidat...

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Published inJournal of organic chemistry Vol. 59; no. 10; pp. 2762 - 2765
Main Authors DesMarteau, Darryl D, Petrov, Viacheslav A, Montanari, Vittorio, Pregnolato, Massimo, Resnati, Giuseppe
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.05.1994
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIDATION
OXAZIRIDINES
CHEMISTRY
DIOXIRANES
SHEEP
RATS
ALBENDAZOLE
DIMETHYLDIOXIRANE
METABOLITE
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Summary:Sulfides are oxidized to sulfoxides by stoichiometric amounts of perfluoro-cis-2,3-dialkyloxaziridines 2. The reactions proceed at -40 degrees C with nearly complete selectivity and very good yields. Sulfoxides are also oxidized easily by 2 under mild conditions to corresponding sulfones. The oxidation of some bioactive sulfides (promazine, albendazole, biotin, and others) is also reported.
Bibliography:istex:4E402311C7B1EBC32668A555C26A7C39531B1D8A
ark:/67375/TPS-FTD20HT0-Z
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00089a020