Nitration of 3,4,6-Tribromo-2,5-dimethylphenol and 3,4,5,6-Tetrabromo- 2-methylphenol; Towards a mechanism of formation of 6-Hydroxy-6-methyl- 2,5-dinitrocyclohex-3-enones

Abstract

The nitrations of the 2-methylphenols (1a) and (1b) give initially 4-nitrocyclohexa-2,5-dienones (6), which undergo further reaction to yield 2,5-dinitrocyclohex-3-enones (4). Reactions of these and other related compounds are reported which point towards a mechanism of formation of substituted 2,5-dinitrocyclohex-3-enones from 2-methylphenols.