191150-84-2

Upstream product

• 33046-41-2 (E)-6-phenyl-3-hexen-2-one 
• 75-91-2 tert.-butylhydroperoxide 
• 33046-41-2 6-phenylhex-3-en-2-one 
• 10027-74-4 2-hydroperoxy-2-methoxypropane 
• 80-15-9 Cumene hydroperoxide 

Relevant academic research and scientific papers

Efficient electrophilic and nucleophilic epoxidations utilizing a sulfonylperoxy radical and peroxysulfate species

Reaction of superoxide anion radical (O2-. with o-nitrobenzenesulfonyl chloride yields a o-nitrobenzenesulfonyl peroxy radical with strong oxidizing ability, which is capable of oxidizing aryl methylene moieties to aryl ketones and relatively electron-rich alkenes regioselectively to epoxides. The oxidizing species is tentatively attributed to the o-nitrobenzenesulfonyl peroxy radical of structure 1. Tetrabutylammonium peroxydisulfate (TBA)2S2O8, 2) was prepared by the reaction of tetrabutylammonium hydrogen sulfate with potassium peroxydisulfate. The epoxidation of enals and enones, such as α,β-unsaturated aldehydes or ketones, was efficiently achieved with 2 in the presence of hydrogen peroxide and base in acetonitrile or in methanol at 25°C. A base-sensitive substrate, such as cinnamaldehyde, could be successfully epoxidized under mild reaction conditions and in short reaction time.

Dearomative Intramolecular (4+3) Cycloadditions of Arenes with Epoxy and Aziridinyl Enolsilanes

An intramolecular (4+3) cycloaddition of epoxy and aziridinyl enolsilanes with benzene, naphthalene, and anthracene derivatives is reported. Highly functionalized polycyclic alcohols and amines are generated under relatively mild reaction conditions with yields up to 89 %. Optically enriched cycloadducts are obtained from cycloadditions of enantiomerically pure epoxides and aziridines.

Catalytic enantioselective peroxidation of α,β-unsaturated ketones

Despite the potential of chiral peroxides as biologically interesting or even clinically important compounds, no catalytic enantioselective peroxidation has been reported. With a chiral catalyst not only to induce enantioselectivity but also to convert a well established epoxidation pathway into a peroxidation pathway, the first efficient catalytic peroxidation has been successfully developed. Employing readily available α,β-unsaturated ketones and hydroperoxides and an easily accessible cinchona alkaloid catalyst, this novel reaction will open new possibilities in the asymmetric synthesis of chiral peroxides. Under different conditions a highly enantioselective epoxidation with the same starting materials, reagents, and catalyst has was also established. Copyright

Highly efficient epoxidation of electron-deficient olefins with tetrabutylammonium peroxydisulfate

The epoxidation of α,β-unsaturated carbonyl compounds such as enones and enals was efficiently achieved with tetrabutylammonium peroxydisulfate in the presence of equimolar amounts of hydrogen peroxide and NaOH in acetonitrile or methanol at 25 °C in excellent yields. Base-sensitive substrate such as cinnamaldehyde could be successfully epoxidized in short reaction time under mild reaction conditions.

Practical epoxidation of α,β-unsaturated ketones with tetra-n-butylammonium peroxydisulfate

α,β-Unsaturated ketones reacted with tetra-n-butylammonium peroxydisulfate in the presence of hydrogen peroxide and base in acetonitrile at 25 °C to give the corresponding epoxides in excellent yields.