The reaction of 4-t-Butyl-2,6-dimethylphenol with nitrogen dioxide ; the formation of four 2,5,6-Trinitrocyclohex-3-enones and 4-t-Butyl-c-6-hydroxy-2,6-dimethyl-r-2,c-5-dinitrocyclohex-3-enone

Abstract

Reaction of 4-t-butyl-2,6-dimethylphenol (13) with nitrogen dioxide in cyclohexane proceeds with some nitro-de-t-butylation, but reaction in benzene yields the four possible 2,5,6-trinitrocyclohex- 3-enones (18), (19), (20), (21) and the hydroxy dinitro ketone (22). The structures and stereochemistry of these products were determined by single-crystal X-ray analysis. The mechanistic significance of the formation of these trinitro ketones (18)-(21) is discussed.