Formation of Thiocarbonyl Compounds in the Reaction of Ebselen Oxide with Thiols

Richard S. Glass, Firdous Farooqui, Mahmood Sabahi, Kenneth W. Ehler

Research output: Contribution to journalArticle

55 Scopus citations

Abstract

Reaction of a-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 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 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.

Original languageEnglish (US)
Pages (from-to)1092-1097
Number of pages6
JournalJournal of Organic Chemistry
Volume54
Issue number5
DOIs
StatePublished - Mar 1 1989

ASJC Scopus subject areas

  • Organic Chemistry

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