Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2006, Issue 11, Pages 2601-2608Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200600061
Keywords
cerium; catalysis; dicarbonyl compounds; oxidation; dioxygen; cyclopropane derivatives
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Three alpha-cyclopropyl beta-dicarbonyl compounds have been used as probes for alpha-radicals as electrophilic reaction intermediates in a cerium-catalyzed alpha-hydroxylation reaction with molecular oxygen. Since the cyclopropyl group did not ring-open to products with a butenyl moiety, but was retained in the products, a localized unpaired electron at the alpha position can be excluded during the course of the reaction. The alpha-cyclopropyl-substituted substrates were prepared by aldol or Claisen reactions. Other substrates with alpha-methyl, aisopropyl, and alpha-tert-butyl substituents were prepared and converted under the a-hydroxylation conditions in order to estimate steric influences on the yield of the reaction.
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