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

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

doi:10.1021/jo00266a018

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

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

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

59 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 language	English (US)
Pages (from-to)	1092-1097
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	54
Issue number	5
DOIs	https://doi.org/10.1021/jo00266a018
State	Published - Mar 1 1989

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Organic Chemistry

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@article{ef44129373404d03bd523f6eb290c22d,

title = "Formation of Thiocarbonyl Compounds in the Reaction of Ebselen Oxide with Thiols",

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.",

author = "Glass, {Richard S.} and Firdous Farooqui and Mahmood Sabahi and Ehler, {Kenneth W.}",

year = "1989",

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day = "1",

doi = "10.1021/jo00266a018",

language = "English (US)",

volume = "54",

pages = "1092--1097",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Formation of Thiocarbonyl Compounds in the Reaction of Ebselen Oxide with Thiols

AU - Glass, Richard S.

AU - Farooqui, Firdous

AU - Sabahi, Mahmood

AU - Ehler, Kenneth W.

PY - 1989/3/1

Y1 - 1989/3/1

N2 - 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.

AB - 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.

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DO - 10.1021/jo00266a018

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 5

ER -

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

Abstract

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