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関連する概念動画

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

8.8K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
8.8K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

11.8K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
11.8K
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

17.7K
Introduction
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.
17.7K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

6.3K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
6.3K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.8K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.8K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.9K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.9K

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関連する実験動画

Updated: Dec 17, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

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シルバー・ナイトレン触媒による分子間アレン機能化

Manuel R Rodríguez1, María Besora2, Francisco Molina1

  • 1Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC, CIQSO-Centro de Investigación en Quı́mica Sostenible and Departamento de Quı́mica, Universidad de Huelva, 21007 Huelva, Spain.

Journal of the American Chemical Society
|June 28, 2020
PubMed
まとめ

シルバー・カタリシスは,アルキラーレンからアゼチジン,アルキラーレンからアジリジンを生成する,効率的な分子間窒素移転を可能にします. これらの製品はさらに価値あるアミノcyclopropanesに変換することができます.

さらに関連する動画

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

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関連する実験動画

Last Updated: Dec 17, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

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科学分野:

  • 有機化学
  • カタリシス
  • 合成方法論

背景:

  • 金属媒介の窒素移転反応は,窒素を含む化合物の合成に不可欠である.
  • アレネは有機合成において多用途の基質であるが,窒素移転剤との反応性はあまり研究されていない.
  • ナイトレンをアルネンに変換するための効率的な触媒システムの開発は,依然として合成の課題です.

研究 の 目的:

  • 最初の効率的な金属媒介型分子間ナイトレンの アレネへの転送を報告する.
  • 反応結果に対するアレン置換剤の影響を調査する.
  • 反応のメカニズムを明らかにし,生成された製品の合成用途を探求する.

主な方法:

  • 反応を媒介するために,銀の触媒前駆体[Tp*,BrAg]2を使用した.
  • 窒素の源としてPHINTSを使用した.
  • 反応経路を理解するために 機械学的な研究を行いました
  • アゼチジンとアジリジンの後の合成変換を調査した.

主要な成果:

  • 効率的な銀触媒による分子間ニートレンの アレネスへの転送を達成した.
  • 代用剤依存の産物形成が示された:アリラレンからアゼチジドンが,アルキラレンからメチレンアジリジンが生成された.
  • アゼチジンの形成のためのサイクロプロピリミン中間物質と,アジリジンの直接の窒素添加を含むメカニズム的経路が提案されています.
  • 合成されたアゼチジジンとアジリジンの有用性をアミノcyclopropanesにさらに変換するために示した.

結論:

  • アルネンへの窒素移転のための新しい銀触媒法を確立した.
  • 反応結果の指示におけるアレン置換剤の重要な役割を強調した.
  • アゼチドイン,アジリジン,アミノcyclopropanesに多用途の合成ルートを提供しました.