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Oxidative Cleavage of C=C Bonds with Singlet Molecular Oxygen Generated from Monoacetylated Bishydroperoxides

Davood Azarifar*, Zohreh Najminejad

*Faculty of Chemistry, Bu-Ali Sina University, 65178 Hamedan, Iran, Email:

D. Azarifar, Z. Najminejad, Synlett, 2013, 24, 1377-1382.

DOI: 10.1055/s-0033-1338947


The oxidative cleavage of C=C bonds adjacent to aryl and alkyl moieties was efficiently achieved with monoacetylated bishydroperoxides. Base-mediated fragmentation of monoacetylated bishydroperoxides generates singlet molecular oxygen as active oxidant in situ. All the reactions furnished the respective carbonyl compounds in good yields at room temperature within short reaction times.

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Key Words

peroxides, alkenes, singlet molecular oxygen, oxidation, aldehydes, ketones

ID: J60-Y2013