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Cerium-Catalyzed Reaction of β-Dicarbonyl Compounds with Styrene and Atmospheric Oxygen

✍ Scribed by Jens Christoffers; Thomas Werner; Wolfgang Frey; Angelika Baro

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
174 KB
Volume
2003
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

The cerium‐catalyzed C−C coupling reaction of carbo‐ and heterocyclic β‐dicarbonyl compounds 1 with styrenes 4, using oxygen (air) as the oxidant, at ambient temperature, is reported. The reaction afforded a mixture of diastereoisomeric hydroperoxides 5 which could be transformed into the unique dioxo compounds 6 by disproportionation of the peroxo function under treatment with acetyl chloride/pyridine. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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## Abstract Three α‐cyclopropyl β‐dicarbonyl compounds have been used as probes for α‐radicals as electrophilic reaction intermediates in a cerium‐catalyzed α‐hydroxylation reaction with molecular oxygen. Since the cyclopropyl group did not ring‐open to products with a butenyl moiety, but was retai