Abstract: Reactions of 1-nitro- and 1,8-dinitronaphthalenes with K2O2 in liquid ammonia at -33°C yield, respectively, mono- and dinitronaphthols. The ratio of the products with 1,2- and 1,4-arrangement of the nitro and hydroxy groups is 1:(1.0-1.3). Lowering the temperature to -60°C results in almost exclusive formation of the 1,4-isomers. Hydroxylation of 1,5-dinitronaphthalene by the action of K2O2 occurs both at the ortho and para positions with respect to the nitro group only in the presence of oxygen. Reactions of 4-chloronitrobenzene and 1,4-dinitrobenzene with K2O2 afford 4-nitrophenol in high yield, whereas nitrobenzene, 4,4′-dinitrobiphenyl, and 1,3-dinitrobenzene do not undergo hydroxylation by the action of K2O2 in liquid ammonia both under argon and in the presence of oxygen.

Cite: Malykhin E.V. , Shteingarts V.D.
Reactions of Aromatic Compounds with Nucleophilic Reagents in Liquid Ammonia. XV. Hydroxylation of Aromatic Nitro Compounds with Potassium Peroxide
Russian Journal of Organic Chemistry. 1997. V.33. N5. P.636-643. Scopus РИНЦ

Identifiers:

Scopus	2-s2.0-0031329376
Elibrary	13265994