1955 年 75 巻 4 号 p. 449-453
The diphenyl ether derivatives possessing a nitro group in the ortho-position undergo hydrazinolysis by the action of hydrazine hydrate at an ordinary pressure. The three kinds of methyl o-nitro-diphenyl ether-carboxylate (I) undergo cleavage of the ether-bond oxygen constituting the diphenyl ether and form o-nitrophenylhydrazine (II) and hydroxybenzoic acid hydrazide (III). (II) further undergoes dehydration and is isolated as 1-hydroxybenzotriazole (IIa) and only a minute amount of the objective o-nitrodiphenyl ether-carboxylic acid hydrazide (IV) is obtained. Similar cleavage occurs in 2-nitrodiphenyl ether-carboxylic acid (V) and 2-nitro-4′-chlorodiphenyl ether but 2-nitrodiphenyl ether and 2-nitromethyldiphenyl ether (VI) do not undergo this cleavage reaction by hydrazine hydrate.