3-Hydroxy-2,6-dinitroacetophenone: an Unusual Substitution Pattern Resulting from Nitration of 3-Hydroxyacetophenone

Article abstract of DOI:10.1107/S0108270195007451

Nitration of 3-hydroxyacetophenone gives 2,6-dinitro-3-hydroxyacetophenone, C8H6N2O6, in which the nitro groups have entered the sterically least favourable positions in the aromatic nucleus.None of the expected substitution in the 4-position was observed.The two nitro groups flanking the carbonyl side chain are different in that one is in the plane of the aryl ring but the other is twisted well out of the plane.