Abstrakt: |
Reaction of 2-hydroxy-3,4,5,6-tetramethylbenzonitrile (1c) with nitrogen dioxide gives predominantly the 4,5,6-trinitrocyclohex-2-enones (9) and (10a,b), with lower yields of the 4-nitro dienone (5a) and the 6-hydroxy-4,5-dinitrocyclohex-2-enone (6). Reaction of 2-hydroxy-3,5-dimethylbenzonitrile (2b) with nitrogen dioxide gave the C4-epimeric 6-hydroxy-4,5-dinitrocyclohex-2-enones (11) and (12). Reaction of 2-hydroxy-3,5,6-trimethyl- benzene-1,4-dicarbonitrile (4) with nitrogen dioxide gave the 4-hydroxy dienone (15) and the 6-hydroxy dienone (16). X-Ray structure determinations are reported for compounds (6), (9) and (11). |