Olefin Epoxidation with Bis(trimethylsilyl) Peroxide Catalyzed by Inorganic Oxorhenium Derivatives. Controlled Release of Hydrogen Peroxide

The replacement of organometallic rhenium species (e.g., CH3ReO3) by less expensive and more readily available inorganic rhenium oxides (e.g., Re2O7, ReO3(OH), and ReO3) can be accomplished using bis(trimethylsilyl) peroxide (BTSP) as oxidant in place of aqueous H2O2. Using a catalytic amount of a p...

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Published inJournal of organic chemistry Vol. 66; no. 13; pp. 4713 - 4718
Main Authors Yudin, Andrei K, Chiang, Jay P, Adolfsson, Hans, Copéret, Christophe
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 29.06.2001
Subjects
Alkenes - chemistry
Catalysis
Hydrogen Peroxide - chemistry
Peroxides - chemistry
Pyridines - chemistry
Rhenium - chemistry
Silanes - chemistry
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Summary:The replacement of organometallic rhenium species (e.g., CH3ReO3) by less expensive and more readily available inorganic rhenium oxides (e.g., Re2O7, ReO3(OH), and ReO3) can be accomplished using bis(trimethylsilyl) peroxide (BTSP) as oxidant in place of aqueous H2O2. Using a catalytic amount of a proton source, controlled release of hydrogen peroxide helps preserve sensitive peroxorhenium species and enables catalytic turnover to take place. Systematic investigation of the oxorhenium catalyst precursors, substrate scope, and effects of various additives on olefin epoxidation with BTSP are reported in this contribution.
Bibliography:ark:/67375/TPS-7X03D4WC-3
istex:599738720856DC29AE226F825DD1E3CD31337193
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo010369m