Formation of thiocarbonyl compounds in the reaction of ebselen oxide with thiols

RS Glass, F Farooqui, M Sabahi…

Index: Glass, Richard S.; Farooqui, Firdous; Sabahi, Mahmood; Ehler, Kenneth W. Journal of Organic Chemistry, 1989 , vol. 54, # 5 p. 1092 - 1097

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Citation Number: 52

Abstract

Reaction of a-toluenethiol with Ebselen oxide, 2, affords dibenzyl disulfide and seleno sulfide 5, R= PhCHP. In the course of this reaction, thiobenzaldehyde is formed and can be trapped with cyclopentadiene in 90% yield. Reaction of 2-propene-1-thiol with 2 afforded thioacrolein dimer in 69% yield and seleno sulfide 5, R= CH2-CH= CH2. Trapping, stereochemical, and isotopic exchange studies were used to determine if in the reaction of ...