Naphthalene 1,8-Disulfide
Naphthalene 1,8-Disulfide
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1,8-二硫化萘
DOI：
10.1021/jo01023a001
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发表时间：
1965
影响因子：
3.6
通讯作者：
A. Hoffmann
中科院分区：
文献类型：
--
作者：
A. Zweig;A. Hoffmann
结果合成。从Desai和Tilak的结果来看，1，8-萘二硫化物（I）似乎是由Lanfrey首先制备的，10他使萘和硫在热铁管中相互作用。Price和Smiles 11也报道了从1-氨基萘-8-磺酸开始制备I。我们最初试图重复价格和微笑的工作是相当混乱的。然而，中间体的表征（参见实验部分），表明，尽管有一些不必要的步骤，这些工人确实准备了I。普莱斯和微笑报告的路径（虚线）和我们发现发生的反应（实线）在图I中描述。因此，二硫化物-二磺酸盐（IV）直接由铜-二氧化硫处理重氮盐（II）获得，并且不需要用碘化氢进一步处理11。用五氧化二磷处理IV并不像以前的工作者所推测的那样得到二磺酰氯9 '11，而是形成环状硫砜（V）（一种新化合物）。用锌-盐酸还原，然后将所得二硫醇（VI）空气氧化，得到I。萘-1，8-二硫醇（VI）也容易甲基化得到1，8-双（甲硫基）萘（VII）。11
ResultsSynthetic.—From the results of Desai and Tilak, 9 it appears that naphthalene 1, 8-disulfide (I) was first prepared by Lanfrey, 10 who caused naphthalene and sulfur to interact in a hot iron tube. Price and Smiles11 also reported the preparation of I, starting with 1-aminonaphthalene-8-sulfonic acid. Our initial attempts to repeat the work of Price and Smiles were rather confusing. Characterization of the intermediates, however (cf. Experimental Section), indicated that, despite some unnecessary steps, these workers had indeed prepared I. The route reported by Price and Smiles (broken lines) and the reactions which we have found to occur(full lines) are depicted in Chart I. Thus, the disulfide-bissulfonic acid salt (IV) is obtained directly from copper-sulfurdioxide treatment of the diazonium salt (II) and further treatment with hydrogen iodide11 is unnecessary. Treat-ment of IV with phosphorus pentachloride does not give the disulfonyl chloride as previous workers had assumed9’11 but rather the cyclic thiosulfone (V)(a new compound) is formed. This, on zinc-hydrochloric acid reduction, followed by air oxidationof the resulting dithiol (VI), gives I. Naphthalene-1, 8-dithiol (VI) is also readily methylated to give 1, 8-bis (methylthio)-naphthalene (VII). 11