The Reactions of Aromatic Carbonyl Compounds with Sodium Hydrosulfide in Liquid Ammonia

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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

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Other Title
  • 芳香族カルボニル化合物に対する硫化水素ナトリウム-液体アンモニア溶液の作用
  • ホウコウゾク カルボモル カゴウブツ ニ タイスル リュウカ スイソ ナトリウム-エキタイ アンモニア ヨウエキ ノ サヨウ
  • The Reactions of Organic Compounds with Sodium Hydrosulfide in Liquid Ammonia. IX
  • 有機化合物に対する硫化水素ナトリウム-液体アンモニア溶液の作用 (第9報)

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Through a series of experimental studies hitherto done, it has been found that in the reactions of the various organic compounds with sodium hydrosulfide in liquid ammonia, nucleophilic substitution, oxidation-reduction and addition reactions take place.<BR>In this paper, the reactions of aromatic carbonyl compounds with sodium hydrosulfide in the presence of ammonium chloride is discussed.<BR>The reaction of benzaldehyde (1) with sodium hydrosulfide and ammonium chloride was carried out in liquid ammonia, and thiobenzamide and benzyl disulfide were obtained. Sodium hydrosulfide and ammonium chloride were let to react with the following aromatic carbonyl compounds in liquid ammonia; 4-anisaldehyde (2), 4-dimethylamino (3) and 4-hydroxybenzaldehyde (4), benzophenone (5), benzil (6) and benzoin (7).<BR>1) In the reactions of (2) and (3), the corresponding thiobenzamide and benzyl disulfide were obtained.<BR>2) In the reaction of (4), 4-hydroxythiobenzamide, 4, 4'-dihydroxybenzyl sulfide and 4-hydroxy benzamidine·2H2O were formed.<BR>3) In the reaction of (5), dibenzhydryldisulfide was the main product.<BR>4) In the reactions of (6) and (7), condensation products and reduction products were formed.

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