129218-82-2Relevant academic research and scientific papers
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.
