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 in:Organic letters 2004-09, Vol.6 (18), p.3119-3122
Main Authors: Murphy, Andrew, Pace, Allyson, Stack, T. Daniel P
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Catalysis
Epoxy Compounds - chemical synthesis
Epoxy Compounds - chemistry
Hydrogen-Ion Concentration
Ligands
Manganese - chemistry
Molecular Structure
Peracetic Acid - chemistry
Stereoisomerism
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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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol048846l