Diazotisation of Aromatic Primary Amines of Weak Basicity (Part 1) -Effects of Inorganic Salts-

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Other Title
  • 弱塩基性芳香族第一アミンのジアゾ化(その1) ―無機塩の影響―
  • 弱塩基性芳香族第一アミンのジアゾ化　Ｉ　　無機塩の影響

Description

In order to disclose side reactions in the diazotisation of aromatic primary amines of weak basicity, the reactions of 6-bromo-2, 4-dinitrobenzenediazonium [1] and 6-chloro-2, 4-dinitrobenzenediazonium compounds C2C'D with some inorganic salts in sulfuric acid have been investigated. In the reaction with NaNO2, [1'] gives not only 2, 3, 5-trinitrobromobenzene but also 1, 2- dibromo-3, 5-dinitrobenzene under a preferential replacement of the -NZ group even in the absence of copper catalyst in strong sulfuric acid. In the reactions with inorganic halides (KF, NaCI, NaBr, KI), [1] gives the corresponding halogen compounds by the replacement of -N2 group except in the case of KF. The yield of the halogen compound varies in the order: FCCl < Br <I.<BR>Similar results are obtained also in the reactions of C2C'. The reactions of dazonium compounds derived from 2, 4-dinitroaniline, p-nitroaniline, and aniline with inorganic halides have also been carried out. However, the, yield of the corresponding halogen compound decreases with decreasing number of the nitro groups on the aromatic nucleus.<BR>These results suggest that the replacement of -N, group in these reactions takes place by a bimolecular mechanism. Nucleophilic reagents of weak basicity and moderate nucleophilicity appear to react even in sulfuric acid with C. M and C2C'D under a cleavage of N2 group to give the corresponding substitution products.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1975 (12), 2178-2182, 1975-12-10

    The Chemical Society of Japan

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