The Reactions of Some Substituted 2-Hydroxybenzonitriles With Nitrogen Dioxide: X-Ray Structures of 2-Cyano-t-6-hydroxy-3,4,5,6-tetramethyl-r-4,t-5-dinitrocyclohex- 2-enone, 2-Cyano-3,4,5,6-tetramethyl-r-4,t-5,t-6-trinitrocyclohex-2-enone and 2-Cyano-c-6-h-4,6-dimethyl-r-4,c-5-dinitrocyclohex-2-enone

Abstract

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).