Notes- Reduction of Conjugated 1,4-Diketones with Tin Amalgam
Notes- Reduction of Conjugated 1,4-Diketones with Tin Amalgam
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注释 - 用锡汞齐还原共轭 1,4-二酮
DOI：
10.1021/jo01081a053
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发表时间：
1960
期刊：
影响因子：
--
通讯作者：
J. Schaefer
中科院分区：
文献类型：
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作者：
J. Schaefer
我们目前正在进行的1，4-二酮氧化反应动力学的研究已经使一系列这类化合物的合成成为必要。由于不饱和1，4-二酮容易获得，烯键的还原为这些物质提供了方便的途径。实现这种转化的常用还原剂是乙酸中的锌;然而，这种还原经常伴随着严重的副反应，这使得它不能作为合成工具。在1，4-二苯基-2-丁烯-1，4-二酮（I）的还原研究中，Lutz 1· 2报道了五种不同的双分子还原产物沿着所需的饱和二酮。为了开发一种可靠的将1，4-烯二酮转化为1，4-二酮的体系，我们寻找了一种更特异的还原剂，我们发现，汞齐化锡和酸将以高产率迅速地将不饱和1，4-二酮还原为饱和衍生物，在所研究的情况下没有任何可检测到的副反应。以锡汞齐和盐酸为还原剂，在乙醇中还原碘得到1，4-二苯基丁烷-1，4-二酮（II），产率90%。1，4-对氯苯基-2-丁烯-
A kinetic study of the oxidation of 1, 4-diketones in which we are currently engaged has necessitated the synthesis of a series of these compounds. Since the unsaturated 1, 4-diketones are readily available, reduction of the olefinic linkage offers a conven-ient route to these substances. The usual reducing agent for effecting this con-version is zinc in acetic acid; however, this reduc-tion is often accompanied by serious side reactions which make it useless as a synthetic tool. In studies on the reduction of 1, 4-diphenyl-2-butene-l, 4-dione (I) Lutz1· 2 has reported the isolation of five different bimolecular reduction products along with the desired saturated diketone. In an effort to develop a reliable system for converting 1, 4-enediones to 1, 4-diones a more specific reducing agent was sought.We have found that amalgamated tin and acid will rapidly reduce unsaturated 1, 4-diketones to the saturated derivative in high yield without any detectable side reactions in the cases studied. Reduction of Iwith tin amalgam and hydrochloric acid in ethanol gave 1, 4-diphenylbutane-l, 4-dione (II) in 90% yield. 1, 4-p-Chlorophenyl-2-butene-