104927-33-5Relevant academic research and scientific papers
REACTION OF AROMATIC COMPOUNDS WITH NUCLEOPHILIC REAGENTS IN LIQUID AMMONIA. VII. DIRECTION OF HYDROXYLATION OF 3-SUBSTITUTED (Cl, Br, I, NO2) NITROBENZENES WITH POTASSIUM HYDROXIDE
Malykhin, E. V.,Kolesnichenko, G. A.,Shteingarts, V. D.
, p. 720 - 726 (2007/10/02)
The reaction of 3-chloro-, 3-bromo-, and 3-iodonitrobenzenes with potassium hydroxide and oxygen in liquid ammonia (-33 deg C) leads to the formation of nitrohalogenophenols, corresponding to substitution of the hydrogen atom at the orto and para positions of the ring in relation to the nitro group by a hydroxy group.In the case of the last two substrates it also leads to the corresponding 2-halogeno-3',4'-dinitrodiphenylamines.In view of the fact that substitued diphenylamines are formed under the same conditions as a result of the reaction of 3-nitroaniline with 3-halogenonitrobenzenes it is suggested that 3-bromo- and 3-iodonitrobenzenes are partly converted into 3-nitroaniline through the intermediate formation of 3-nitrodehydrobenzene.During dehydroxylation in the absence of oxygen the proportion of the phenols corresponding to substitution of the hydrogen atom at the para position to the nitro group by the hydroxy group increases, and the degree of transformation of the inital compounds decreases. 2,4-Dinitrophenol is formed with a low yield during the reaction of 1,3-nitrobenzene and potassium hydroxide in the presence of oxygen or in an atmosphere of argon.
