Journal of Organic Chemistry p. 1092 - 1097 (1989)
Update date:2022-07-31
Topics:
Glass, Richard S.
Farooqui, Firdous
Sabahi, Mahmood
Ehler, Kenneth W.
Reaction of α-toluenethiol with Ebselen oxide, 2, affords dibenzyl disulfide and seleno sulfide 5, R = PhCH2.In the course of this reaction, thiobenzaldehyde is formed and can be trapped with cyclopentadiene in 90percent yield.Reaction of 2-propene-1-thiol with 2 afforded thioacrolein dimer in 69percent yield and seleno sulfide 5, R = CH2-CH=CH2.Trapping, stereochemical, and isotopic exchange studies were used to determine if in the reaction of 2 with 1-heptanethiol, cyclohexanethiol, and N-acetyl-D,L-cysteine thiocarbonyl compounds heptanethial, cyclohexanethione, and 2-acetamino-3-thioxopropanoic acid (α-thioformyl-N-acetylglycine), respectively, are also formed.These studies showed that free thiocarbonyl compounds are not formed in these reactions.
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