Difference Between Clemmensen and Wolff Kishner Reduction

Thekey differencebetween Clemmensen and Wolff Kishner reduction is that theClemmensen reduction involves the conversion ofketone或者醛intoalkaneswhereas the Wolff Kishner reduction involves the conversion ofcarbonylgroups into methylene groups.

Both these processes do these conversions via reducing the functional groups. Therefore, these processes require specific reaction conditions and catalysts for the successful progression of the reaction. Since the reactants for each process are organic molecules, we use these processes in organic synthesis reactions.

内容

1.Overview and Key Difference
2.What is Clemmensen Reduction
3.What is Wolff Kishner Reduction
4.Side by Side Comparison – Clemmensen vs Wolff Kishner Reduction in Tabular Form
5.概括

What is Clemmensen Reduction?

Clemmensen reduction is an organic chemical reaction in which we convert a ketone or aldehydes into an alkane. We need to use a catalyst for this reaction; it is amalgamated zinc (mercury alloyed with zinc ) with hydrochloric acid. Therefore, the mercury alloyed with zinc does not participate in the reaction. It only provides a clean, active surface for the reaction. The name of the processes derived after the Danish scientist Erik Christian Clemmensen.

This process is highly effective in the reduction of aryl-alkyl ketones. Moreover, the zinc metal reduction is much more effective with aliphatic or cyclic ketones. More importantly, the substrate of this reaction has to be unreactive towards the strongly acidic conditions of the reaction.

What is Wolff Kishner Reduction?

Wolff Kishner reduction is an organic chemical reaction that we use to convert a carbonyl functional group into a methylene group. This reaction got its name after the two scientists Nikolai Kirschner and Ludwig Wolff. The major applications of this reaction are in the synthesis of scopadulcic acid B, aspidospermine and dysidiolide.

与Clemmensen还原不同，该反应需要强烈的基本条件。因此，在反应过程中，第一步是通过与酮或醛底物的缩合缩合氢氮。然后，作为第二步，我们应该使用烷氧化物碱脱皮。之后，出现了二imide阴离子形成的步骤。然后这个阴离子崩溃了n₂gas, and it leads to the formation of an alkylation. Eventually, we can protonate this alkylation to get the desired product.

Clemmensen和狼之间的区别是什么f Kishner Reduction?

Clemmensen and Wolff Kishner reduction is very important in the organic synthesis of different chemical compounds. However, the key difference between Clemmensen and Wolff Kishner reduction is that the Clemmensen reduction involves the conversion of ketone or aldehydes into alkanes whereas the Wolff Kishner reduction involves the conversion of carbonyl groups into methylene groups. Moreover, we use a catalyst in the Clemmensen reduction reaction; it is amalgamated zinc. But we do not use a catalyst for Wolff Kishner reduction reaction. Another difference between Clemmensen and Wolff Kishner reduction is that Clemmensen reduction uses strongly acidic conditions, hence not suitable for acid-sensitive substrates. Whereas, Wolff Kishner reduction uses strongly basic conditions; thus, not suitable for base sensitive substrates.

The below infographic tabulates the difference between Clemmensen and Wolff Kishner reduction in more detail.

概括– Clemmensen vs Wolff Kishner Reduction

我们在有机化学中使用许多不同的有机化学反应来合成重要化合物。因此，克莱门森和沃尔夫·基什纳的还原是这两个反应。Clemmensen和Wolff Kishner还原之间的关键区别在于，Clemmensen还原涉及酮或醛向烷烃的转化，而Wolff Kishner还原涉及将羰基基团转化为甲基烯基团。

Reference:

1.库。“莱克门森还原。”Chemistry libretexts，libretexts，2017年8月6日。Available here
2. “Wolff–Kishner Reduction.” Wikipedia, Wikimedia Foundation, 26 July 2018.Available here

Image Courtesy:

1.“克莱姆门森减少计划”（公共领域）通过Commons Wikimedia
2.”Wolff-Kishner-reaction scheme-new”By C kleinlein – Own work,(CC BY-SA 3.0)viaCommons Wikimedia