Hydrophobic/hydrophilic effects on the titanium(IV)-catalyzed epoxidation of cyclohexene by tert-alkyl hydroperoxides: 2-methyl-l-phenyl-2-propyl hydroperoxide (MPPH) versus tert-butyl hydroperoxide (TBHP)

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DOIResolve DOI: http://doi.org/10.1023/A:1019074920329
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TypeArticle
Journal titleCatalysis Letters
ISSN1011-372X
Volume48
Issue1-Feb
Pages2124; # of pages: 4
AbstractThe epoxidation of cyclohexene in acetonitrile under argon at room temperature on a titanium(IV)-containing MCM41 silica catalyst is faster and gives a greater final yield of cyclohexene oxide when the oxygen atom donor is 2-methyl-l-phenyl-2-propyl hydroperoxide (MPPH) than when it is tert-butyl hydroperoxide. This is shown to be due to stronger retardation of the oxidation by tert-butyl alcohol (TBA) than by the alcohol derived from MPPH. The difference in retardation between these two alcohols is attributed to the greater hydrophilicity of TBA. Acetonitrile is a better solvent for this reaction than isooctane, pyridine and a variety of alcohols. These solvent effects are attributed to the hydrophilic nature of the catalyst.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC)
Peer reviewedYes
NPARC number21276590
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Record identifierefbb797c-5cf7-47f6-b615-3201e76f045d
Record created2015-10-13
Record modified2016-05-09
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