Study of Oxidation of Terminal Unsaturated Compounds by Reagents Based on Dimethylsulfoxide

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Abstract

The products of reactions of styrene, phenylacelylene, and 1-bromo-1-phenylethane with HBr and Br2 in DMSO were studied for the first time by high-performance liquid chromatography and gas chromatography-mass spectrometry. Phenylglyoxal is the main product in the reactions with styrene and bromophenylethane, while dibromostyrenes are formed as the main products in the reaction with phenylacetylene. Schemes of the reactions of these substrates with the reagents are proposed. The reactions of nucleophilic addition and decomposition of the dimethylsulfoxonium salts formed are the key stages of the processes considered.

Original languageEnglish
Pages (from-to)153-157
Number of pages5
JournalRussian Journal of Organic Chemistry
Volume33
Issue number2
Publication statusPublished - Feb 1997

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Unsaturated compounds
Styrene
Dimethyl Sulfoxide
Phenylglyoxal
Oxidation
High performance liquid chromatography
Gas chromatography
Mass spectrometry
Salts
Decomposition
Substrates

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "The products of reactions of styrene, phenylacelylene, and 1-bromo-1-phenylethane with HBr and Br2 in DMSO were studied for the first time by high-performance liquid chromatography and gas chromatography-mass spectrometry. Phenylglyoxal is the main product in the reactions with styrene and bromophenylethane, while dibromostyrenes are formed as the main products in the reaction with phenylacetylene. Schemes of the reactions of these substrates with the reagents are proposed. The reactions of nucleophilic addition and decomposition of the dimethylsulfoxonium salts formed are the key stages of the processes considered.",
author = "Krasnokutskaya, {E. A.} and W. Habicher and Yusubov, {M. S.} and Filimonov, {V. D.}",
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AU - Filimonov, V. D.

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