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Updated: May 2, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Published on: June 21, 2017

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同型アミンを生成する1,3-ダイエンの分子間水酸化

Xiao-Hui Yang1, Alexander Lu1, Vy M Dong1

  • 1Department of Chemistry, University of California, Irvine , Irvine, California 92697, United States.

Journal of the American Chemical Society
|September 28, 2017
PubMed
まとめ

研究者らは,1,3-ジーンからホモアリルアミンを合成するための新しいRh触媒反応を開発した. この方法は,特定のリガンドと酸性添加物を用いて,分子間アミンと1,3-ディエンの結合で初めて報告された抗マルコヴニコフ選択性を達成します.

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An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
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Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
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Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...
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