有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
9-アミノフェナントレンのスルホン化
太田 悦郎岡田 安雄
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ジャーナル フリー

1966 年 24 巻 1 号 p. 39-43

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9-Aminophenanthrene (1) gave an aminophenanthrene sulfonic acid (3) almost free from the isomers upon baking its bisulfate under various conditions. An excellent yield (98%) was attained when the reaction was carried out at 220°C under 4 mmHg. The structure of (3) was determined to be 9-aminophenanthrene-3- sulfonic acid based on the facts that (3) was synthesized by ammonolysis of 9-bromophenanthrene -3-sulfonic acid (2) and that (2) was derived by the Sandmeyer reaction from (3). Direct sulfonation of (1) with concentrated sulfuric acid proceeded with great ease and gave a mixed product of monosulf onic acids and polysulf onic acids even when the reaction was conducted at a low temperature so as to retain the major portion of the (1) unreacted. Trials to separate the mixture into its components failed to succeed.
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