76641-15-1Relevant academic research and scientific papers
ipso-Attack in the Nitration of Aromatic Amines. Part 2. Isolation of Salts and Other Products resulting from ipso-Attack
Helsby, Paul,Ridd, John H.
, p. 311 - 316 (2007/10/02)
In 70percent nitric acid at 0 deg C, NN,2,4,6-pentamethylaniline undergoes ipso-attack at the 4-position to form the relatively stable ipso-intermediate (2); this ion can be precipitated as the hexafluorophosphate.In more aqueous media, the dimethylamino group is displaced by water to form the hexadienone (4).In aqueous nitric acid at 0 deg C, NN,2,4-tetramethyl-6-nitroaniline undergoes both ipso-attack and addition of water to the ring to form the adduct (8); this ion can also be precipitated as the hexafluorophosphate.The reaction of NN,2,6-tetramethyl-4-methoxyaniline with 52 percent nitric acid at 0 deg C also involves displacement of the dimethylamino group and gives finally 2,6-dimethylbenzoquinone.The initial stages of the reactions of the above amines require the presence of nitrous acid and the reactions are inhibited by hydrazine.
Isolation and Further Reactions of Charged Species resulting from ipso-attack in the Nitration of Aromatic Amines
Helsby, Paul,Ridd, John H.
, p. 926 - 927 (2007/10/02)
Charged species resulting from ipso-attack in the nitration of aromatic amines can be precipitated as hexafluorophosphates but the isolation is complicated by addition and substitution reactions involving water in the solvent.
