酮和胺在過(guò)量的甲酸作為還原劑的條件下進(jìn)行還原胺化的反應(yīng)。當(dāng)用醛作為底物的反應(yīng)為Eschweiler–Clarke還原胺化反應(yīng)。
反應(yīng)機(jī)理
胺先親核進(jìn)攻酮生成胺基醇,脫水得到亞胺離子中間體,甲酸還原得到產(chǎn)物
反應(yīng)實(shí)例
Leuckart–Wallach反應(yīng)后通過(guò)Wagner-Meerwein遷移進(jìn)行分子內(nèi)的胺基遷移得到產(chǎn)物。
參考文獻(xiàn)
1. Leuckart, R. Ber. 1885, 18, 2341-2344. Carl L. R. A. Leuckart (1854-1889) was born in Giessen, Germany. After studying under Bunsen, Kolbe, and von Baeyer, he became an assistant professor at G?ttingen. Unfortunately, chemistry lost a brilliant contributor by his sudden death at age 35 as a result of a fall in his parent’s house.【Carl L. R. A. Leuckart (1854-1889)生于德國(guó)吉森, 后來(lái)師從于 Bunsen, Kolbe, 和von Baeyer,稱為哥根廷大學(xué)副教授,可惜在35歲意外死亡,對(duì)于化學(xué)界是巨大的損失。】
2. Wallach, O. Ann. 1892, 272, 99. Otto Wallach (1847-1931), born in K?nigsberg, Prussia, studied under W?hler and Hofmann. He was the director of the Chemical Institute at G?ttingen from 1889 to 1915. His book “Terpene und Kampfer” served as the foundation for future work in terpene chemistry. Wallach was awarded the Nobel Prize in Chemistry in 1910 for his work on alicyclic compounds.【Otto Wallach (1847-1931)生于普魯士的哥尼斯堡,師從于W?hler 和 Hofmann。在1889年到1915年出任哥根廷大學(xué)化學(xué)研究所大學(xué)主任。他所著的《萜烯和樟腦》為后來(lái)萜烯化學(xué)奠定了基礎(chǔ)。Wallach由于在脂環(huán)化合物方面的研究獲得了1910年的諾貝爾化學(xué)獎(jiǎng)。】
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編譯自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Leuckart–Wallach reaction,page 362-363.