Liquid-phase oxidation of deactivated methylbenzenes by aqueous sodium hypochlorite catalyzed by ruthenium salts under phase-transfer catalytic conditions

Yoel Sasson, Guillermo D. Zappi, Ronny Neumann

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55 Citations (Scopus)

Abstract

Toluene and methylbenzene ring substituted with electron-withdrawing substituents were oxidized to the corresponding carboxylic acids. The oxidation system is biphasic consisting of an organic substrate phase and an aqueous sodium hypochlorite phase with both ruthenium and quaternary ammonium salts acting as catalysts. Yields are essentially quantitative after 2 h at room temperature with a stoichiometric ratio hypochlorite/toluene of 4.5:1 provided the pH of the aqueous phase is between 8.0 and 10.5. Kinetic studies show the reaction to be of first order in the substrate, zero order in sodium hypochlorite, and combined first order in the catalysts. The reaction mechanism consists of a RuO4-catalyzed hydride abstraction and a phase-transfer-catalyzed proton-dependent step.

Original languageEnglish
Pages (from-to)2880-2883
Number of pages4
JournalJournal of Organic Chemistry
Volume51
Issue number15
Publication statusPublished - 1986

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Sodium Hypochlorite
Ruthenium
Toluene
Salts
Hypochlorous Acid
Oxidation
Catalysts
Proton transfer
Liquids
Substrates
Carboxylic Acids
Ammonium Compounds
Hydrides
Kinetics
Electrons
Temperature

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Liquid-phase oxidation of deactivated methylbenzenes by aqueous sodium hypochlorite catalyzed by ruthenium salts under phase-transfer catalytic conditions",
abstract = "Toluene and methylbenzene ring substituted with electron-withdrawing substituents were oxidized to the corresponding carboxylic acids. The oxidation system is biphasic consisting of an organic substrate phase and an aqueous sodium hypochlorite phase with both ruthenium and quaternary ammonium salts acting as catalysts. Yields are essentially quantitative after 2 h at room temperature with a stoichiometric ratio hypochlorite/toluene of 4.5:1 provided the pH of the aqueous phase is between 8.0 and 10.5. Kinetic studies show the reaction to be of first order in the substrate, zero order in sodium hypochlorite, and combined first order in the catalysts. The reaction mechanism consists of a RuO4-catalyzed hydride abstraction and a phase-transfer-catalyzed proton-dependent step.",
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T1 - Liquid-phase oxidation of deactivated methylbenzenes by aqueous sodium hypochlorite catalyzed by ruthenium salts under phase-transfer catalytic conditions

AU - Sasson, Yoel

AU - Zappi, Guillermo D.

AU - Neumann, Ronny

PY - 1986

Y1 - 1986

N2 - Toluene and methylbenzene ring substituted with electron-withdrawing substituents were oxidized to the corresponding carboxylic acids. The oxidation system is biphasic consisting of an organic substrate phase and an aqueous sodium hypochlorite phase with both ruthenium and quaternary ammonium salts acting as catalysts. Yields are essentially quantitative after 2 h at room temperature with a stoichiometric ratio hypochlorite/toluene of 4.5:1 provided the pH of the aqueous phase is between 8.0 and 10.5. Kinetic studies show the reaction to be of first order in the substrate, zero order in sodium hypochlorite, and combined first order in the catalysts. The reaction mechanism consists of a RuO4-catalyzed hydride abstraction and a phase-transfer-catalyzed proton-dependent step.

AB - Toluene and methylbenzene ring substituted with electron-withdrawing substituents were oxidized to the corresponding carboxylic acids. The oxidation system is biphasic consisting of an organic substrate phase and an aqueous sodium hypochlorite phase with both ruthenium and quaternary ammonium salts acting as catalysts. Yields are essentially quantitative after 2 h at room temperature with a stoichiometric ratio hypochlorite/toluene of 4.5:1 provided the pH of the aqueous phase is between 8.0 and 10.5. Kinetic studies show the reaction to be of first order in the substrate, zero order in sodium hypochlorite, and combined first order in the catalysts. The reaction mechanism consists of a RuO4-catalyzed hydride abstraction and a phase-transfer-catalyzed proton-dependent step.

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