Diphenyl Etherを基核とするAcid Hydrazide誘導体の合成研究 (第14報)

Diphenyl Ether誘導体のHydrazine Hydrateによる開裂反応 その8

抄録

Diphenyl ether derivatives possessing hydroxyl in different positions, with the nitro group present in the position para to the phenoxyl, hardly submits to cleavage of ether-oxygen forming a diphenyl ether by the action of hydrazine hydrate at ordinary pressure which the reaction proceeds at higher pressure to form 4-nitrophenylhydrazine (II) and the corresponding amino-hydroxydiphenyl ether derivative (V). Under some conditions, (II) is further decomposed to nitrobenzene (IIa) and 4-nitroaniline (IIb) (cf. Chart 1).
When the nitro group is present in the position ortho to the phenyl, hydrazinolysis occurs easily to form 2-nitrophenylhydrazine (IX) and the corresponding dihydrobenzene derivative. Of these, (IX) easily undergoes dehydration reaction to form 1-hydroxybenzotriazole (IXa) (cf. Chart 3).