34013-60-0Relevant articles and documents
The first preparation of episulfones from episulfides: Oxidation using Oxone/trifluoroacetone
Johnson, Paul,Taylor, Richard J. K.
, p. 5873 - 5876 (1997)
For the first time, episulfones have been prepared by oxidation of the corresponding episulfides. Seven examples are given, most of which proceed in good to excellent yield. The first oxidation of an episulfoxide to an episulfone is also reported as part of a preliminary mechanistic study.
REACTIONS OF EPISULPHOXIDES AND EPISULPHIDES WITH ORGANOLITHIUM REAGENTS
Bonini, Bianca F.,Maccagnani, Gaetano,Mazzanti, Germana,Zani, Paolo
, p. 115 - 121 (2007/10/02)
Reactions of aryl-substituted episulphoxides and episulphides with butyl- and phenyllithium, lithium di-isopropyl amide and lithium dimethylcuprate have been examined.The following reaction paths could be observed: a) attack at sulphur leading to olefins with complete retention of configuration at the carbon skeleton; b) attack at proton leading to a vinyl sulphenate in the case of episulphoxides, or to a thiolate anion, in the case of episulphides, trapped as methyl vinyl sulphoxide or methyl vinyl sulphide, respectively; c) attack at carbon, observed only in thereaction of styrene episulphoxide with lithium dimethylcuprate, leading to a saturated sulphenate anion trapped as alkyl methyl sulphoxide.Mechanisms and stereochemistry of these processes are discussed.
