The nitration of 4-Nitro- and 4-Bromo-2,6-dimethylphenols; X-Ray Crystal Structures of t-6-Hydroxy-2,6-dimethyl-r-2,4,t-5-trinitrocyclohex-3-enone, r-2,t-6-Dihydroxy-2,6-dimethyl-4,t-5-dinitrocyclohex-3-enone and 4-Bromo-t-6-hydroxy-2,6-dimethyl-r-2,t-5-dinitrocyclohex-3-enone

Abstract

The nitration of 2,6-dimethyl-4-nitrophenol (1b), with either fuming nitric acid in acetic acid or nitrogen dioxide in dichloromethane, gives the C2-epimeric hydroxy trinitro ketones (4) and (5), the dinitro phenol (6) and the dihydroxy dinitro ketone (7). The nitration of the 4-bromo phenol (1c) is accompanied by some nitro- debromination and compounds (4), (5) and (13)-(17) are isolated. X-ray structure determinations are reported for compounds (5), (7) and (14).