Selenoxides as catalysts for epoxidation and Baeyer-Villiger oxidation with hydrogen peroxide

Aryl benzyl selenoxides are catalysts for the epoxidation of various olefinic substrates and the Baeyer-Villiger oxidation of aldehydes and ketones with H2O2 in CH2Cl2 at 2.5 mol% catalyst. Benzyl 3,5-bis(trifluoromethyl)phenyl selenoxide (4) was the most effective catalyst while 2-(dimethylamino)ph...

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Bibliographic Details
Published inSynlett no. 7; pp. 1100 - 1104
Main Authors Goodman, Margaret A., Detty, Michael R.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 03.05.2006
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
esters
selenoxide
ACIDS
STEPWISE MECHANISM
catalysis
METHYLTRIOXORHENIUM(VII)
ORGANOTELLURIUM(II) COMPOUNDS
SYN-ELIMINATION
oxidations
ALLYLIC ALCOHOLS
ORGANOSELENIUM CHEMISTRY
epoxidations
HOMOGENEOUS SOLUTION
OLEFINS
SELENIUM DIOXIDE
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Summary:Aryl benzyl selenoxides are catalysts for the epoxidation of various olefinic substrates and the Baeyer-Villiger oxidation of aldehydes and ketones with H2O2 in CH2Cl2 at 2.5 mol% catalyst. Benzyl 3,5-bis(trifluoromethyl)phenyl selenoxide (4) was the most effective catalyst while 2-(dimethylamino)phenyl benzyl selenoxide was the least. Mono-, di-, and trisubstituted alkenes were epoxidized and adarnantanone, cyclohexanone, and 3,4,5-trimethoxybenzaidehyde underwent Baeyer-Villiger oxidation using 4 and H2O2. Competition studies showed that epoxidation reactions were faster than Baeyer-Villiger oxidations although the selectivity varied only from 1.3:1 to 4.6:1.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2006-939692