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Kinetics and mechanism of RuCl2PPh3)3-catalyzed oxidation of sulfides by N-methylmorpholine N-oxide
Jayaraman Rajaram, Joseph C. Kuriacose
Published in
1989
Volume: 49
   
Issue: 2
Pages: 153 - 163
Abstract
Oxidation of dibutylsulfide, diphenylsulfide, methylphenylsulfide and dibenzylsulfide to the corresponding sulfoxides by N-methylmorpholine N-oxide (NMO) catalyzed by RuCl2(PPh3)3 in DMF solvent is reported. The reaction is first order in both catalyst and N-oxide. The order with respect to the substrate is variable, being zero at higher concentrations and fractional at lower concentrations. The order of reactivity observed for the substrates is as follows: dibutylsulfide ≈ dibenzylsulfide > methylphenylsulfide > diphenylsulfide. RuCl2(PPh3)3 oxidizes olefins to form epoxides at a slower rate. The order of reactivity observed for the two types of substrates parallels their nucleophilicity (sulfides > alkenes). Spectral studies indicate 1:1 complex formation between RuCl2(PPh3)3 and the sulfides. The active oxidant is the Ru(IV)oxo complex formed by the oxidation of Ru(II) by NMO. © 1989.
About the journal
JournalJournal of Molecular Catalysis
ISSN03045102
Open AccessNo
Concepts (11)
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    Catalysis--reaction kinetics
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    CATALYSTS--RUTHENIUM COMPOUNDS
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    ORGANIC COMPOUNDS--CATALYSIS
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    Organometallics--applications
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    DIBENZYLSULFIDE
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    DIBUTYLSULFIDE
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    DICHLOROTRIS(TRIPHENYL PHOSPHINE)RUTHENIUM
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    DIPHENYLSULFIDE
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    METHYLMORPHOLINE OXIDE
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    METHYLPHENYLSULFIDE
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    SULFUR COMPOUNDS