Ligand and pH Influence on Manganese-Mediated Peracetic Acid Epoxidation of Terminal Olefins

Nineteen MnII complexes were screened for the catalytic epoxidation of terminal olefins using peracetic acid. Few of these complexes are efficient catalysts at pH < 2, but many are effective at 1 mol % catalyst loading at pH 4. With 0.1 mol % loading, four complexes epoxidize 1-octene in ∼80% yie...

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Bibliographic Details
Published inOrganic letters Vol. 6; no. 18; pp. 3119 - 3122
Main Authors Murphy, Andrew, Pace, Allyson, Stack, T. Daniel P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.09.2004
Amer Chemical Soc
Subjects
Alkenes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Epoxy Compounds - chemical synthesis
Epoxy Compounds - chemistry
Hydrogen-Ion Concentration
Ligands
Manganese - chemistry
Molecular Structure
Peracetic Acid - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
MECHANISM
COMPLEXES
HYDROGEN-PEROXIDE
ALKENE EPOXIDATIONS
H2O2
CATALYSTS
ELECTRON-DEFICIENT OLEFINS
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Summary:Nineteen MnII complexes were screened for the catalytic epoxidation of terminal olefins using peracetic acid. Few of these complexes are efficient catalysts at pH < 2, but many are effective at 1 mol % catalyst loading at pH 4. With 0.1 mol % loading, four complexes epoxidize 1-octene in ∼80% yield in 5 min. The relative reactivity of the catalysts toward different olefins was probed using a multicomponent intermolecular competition reaction.
Bibliography:Medline
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ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol048846l