The Reactions of Aromatic Nitro Compounds with Sodium Hydrosulfide in Liquid Ammoniat

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  • TAKIKAWA Yuji
    Department of Applied Chemistry, Faculty of Engineering, Iwate University
  • TAKIZAWA Saburo
    Department of Applied Chemistry, Faculty of Engineering, Iwate University

Bibliographic Information

Other Title
  • 液体アンモニア中における芳香族ニトロ化合物と硫化水素ナトリウムとの反応

Description

As an extension of our series of experimental studies on nucleophilic substitution reaction of halobenzenes and halonitrobenzenes with NaSH in liquid ammonia, the reactions of aromatic nitro compounds with NaSH have been investigated.<BR>ms-Dianthryldisulfide was obtained nearly quantitatively by the reaction of 9-nitroanthracene [1] with NaSH in liquid ammonia.<BR>The reactions of following aromatic nitro compounds with NaSH were carried out in liquid ammonia; 1, 2-dinitrobenzene[2], 1-nitronaphthalene[3], 2-[4] and 4-nitrotoluenes[5], nitrobenzene C6j, 1, 3-dinitrobenzene[7], 2-nitroaniline[8], 4-nitrophenetole[9] and 4-nitrobiphenyl [10].<BR>The results are summarized as follows.<BR>1) In the reaction of [2], 2, 2'-dinitrodiphenyldisulfide was obtained.<BR>2) In the reaction of [3], 4, 4'-dinitrodinaphthyldisulfide and 4, 4'-diaminodinaphtyldisulfide were obtained.<BR>3) The methyl group was oxidized and the nitro group was reduced in the products of the reactions of [4] and [5].<BR>4) In the reactions of aromatic nitro compounds such as [6], [7], [8], [9] and [10], the corresponding substituted aniline and substituted azobenzene were preferentially obtained.<BR>The reaction mechanism are discussed.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1972 (4), 761-765, 1972-04-10

    The Chemical Society of Japan

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