91734-80-4Relevant academic research and scientific papers
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
Hartshorn, Michael P.,Readman, Jennifer M.,Robinson, Ward T.,Vaughan, John,Whyte, Andrew R.
, p. 1693 - 1704 (2007/10/02)
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).
The Reaction of 4-t-Butyl-2,6-dimethylphenol with Nitrogen Dioxide; the Formation of Four 2,5,6-Trinitrocyclohex-3-enones and 4-t-Butyl-c-6-hydroxy-2,6-dimethyl-r-2,c-5-dinitrocyclohex-3-enone
Hartshorn, Michael P.,Penfold, Bruce R.,Sutton, Kevin H.,Vaughan, John
, p. 809 - 818 (2007/10/02)
Reaction of 4-t-butyl-2,6-dimethylphenol (13) with nitrogen dioxide in cyclohexane proceeds with some nitro-de-t-butylation, but reaction in benzene yields the four possible 2,5,6-trinitrocyclohex-3-enones (18), (19), (20), (21) and the hydroxy dinitro ketone (22).The structures and stereochemistry of these products were determined by single-crystal X-ray analysis.The mechanistic significance of the formation of these trinitro ketones (18)-(21) is discussed.
