
TY  - JOUR
A1  - Hartshorn, MP 
A1  - Robinson, WT 
A1  - Waller, AG 
A1  - Wright, GJ 
T1  - Reactions of 6-Benzyl-2-t-butyl-4,6-dimethyl-cyclohexa-2,4-dienone and 6-Benzyl-4-t-butyl-2,6-dimethylcyclohexa-2,4-dienone With Nitrogen Dioxide
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1989
VL  - 42
IS  - 9
SP  - 1547
EP  - 1568
KW  - 
UR  - https://doi.org/10.1071/CH9891547 
N2  - Reaction of the 2-t-butyl-4-methylcyclohexa-2,4-dienone (7) with nitrogen dioxide in benzene gives the four 4,5-dinitrocyclohex-2-enones (9)-(12), the three 2,5-dinitrocyclohex-3-enones (13)-(15), and the 2-hydroxy-5-nitrocyclohex-3-enone (17). Under the same reaction conditions the 4-t-butyl-2-methylcyclohexa-2,4-dienone (8) gives the four 2,5-dinitrocyclohex-3-enones (19)-(22), and the three 2-hydroxy-5-nitrocyclohex-3-enones (23)-(25). X-Ray structure determinations are reported for compounds (9), (10), (13), (14), (19) and (25). In solution at 40 the dinitro ketone (20) rearranges to give dinitro ketone (19) and 2-hydroxy-5-nitro ketones (23) and (24). The reaction mechanisms for the various reactions are discussed. 
ER  -

