The oxidation of acetophenones to arylglyoxals with aqueous hydrobromic acid in dimethyl sulfoxide

MB Floyd, MT Du, PF Fabio, LA Jacob…

Index: Floyd, M. Brawner; Du, Mila T.; Fabio, Paul F.; Jacob, Linda A.; Johnson, Bernard D. Journal of Organic Chemistry, 1985 , vol. 50, # 25 p. 5022 - 5027

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Citation Number: 87

Abstract

The reaction of acetophenones with aqueous hydrobromic acid (HBr) in dimethyl sulfoxide (MezSO) leads to the formation of arylglyoxals in good yield. Evidence has been obtained which suggests that this oxidation is mediated by a low concentration of molecular bromine, with the consecutive intermediacy of the a-bromoand a-hydroxyacetophenones. The reaction of a-bromoacetophenone 2 with MelSO alone provides the arylglyoxal 4 with the ...