The nitration of pentamethylphenol

Abstract

Nitration of pentamethylphenol (1) with nitrogen dioxide in benzene gives the four possible 2,5,6-trinitrocyclohex-3-enones (6), (7), (8) and (9), three 4,5,6-trinitrocyclohex-2-enones (10), (11) and [(12) or (13)], the 2-hydroxy-5,6-dinitrocyclohex-3-enone (14), quinone (17) and the 4-nitro dienone (3). The fuming nitric acid nitration of pentamethylphenol (1) for 90 h gives most of these products, except that 4-nitratomethyl-2,5,6-trinitrocyclohex-3-eones (21), (22), (23) and (24) are isolated. X-ray crystal structures are reported for compounds (6), (7), (8), (10), (11), (14) and (21).