The products obtained when acetophenones are heated with nitric acid in the presence of acetic anhydride vary depending on the substituent on the aromatic ring. In most cases, when acetophenone or a substituted acetophenone is heated with nitric acid in the presence of acetic anhydride, the product obtained is a symmetrically substituted 3,4-dibenzoyloxadiazole-2-oxide (dibenzoylfuroxan). However, hydroxy-substituted acetophenones do not form furoxans under these conditions. Nitration of 4-hydroxyacetophenone yields 2,4-dinitrophenol and the acetyl group is lost. The purpose of this research is to elucidate the reaction mechanisms and understand why hydroxy-substituted acetophenones undergo substitution at the aromatic ring rather than the alpha carbon.

Reactions of acetophenones with nitric acid: The effect of ring substitution on α-nitration versus electrophilic aromatic substitution

255th National Meeting (2018)

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