The direct ketohydroxylation of a variety of 1-aryl-1-alkenes with H2O2, catalyzed by the inexpensive 12-tungstophosphoric acid/cetylpyridinium chloride system under very mild conditions, was achieved. Various acyloins were obtained in good yields and high regioselectivies.
Ketones Q 0350 Direct, Efficient, and Inexpensive Formation of α-Hydroxyketones from Olefins by Hydrogen Peroxide Oxidation Catalyzed by the 12-Tungstophosphoric Acid/ Cetylpyridinium Chloride System. -For substrates without an aromatic ring attached to the sp 2 carbon only epoxidation is observed. Alkenes with electron-withdrawing groups on C-2 show no reaction. 1,1-Disubstituted and trisubstituted ethylene derivatives are cleaved to give ketones (VII). -(ZHANG, Y.; SHEN, Z.; TANG, J.; ZHANG, Y.; KONG, L.; ZHANG*, Y.; Org.
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