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関連する概念動画

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.4K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
2.4K
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

2.3K
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
2.3K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

9.1K
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.
9.1K
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

10.8K
Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone. 
When dissolved in liquid ammonia, an alkali metal, such as sodium,...
10.8K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

2.9K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
2.9K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

3.1K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
3.1K

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Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes
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Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

Published on: January 30, 2015

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触媒的還元性ビニリデンの転移反応

Sudipta Pal1, You-Yun Zhou1, Christopher Uyeda1

  • 1Department of Chemistry, Purdue University , West Lafayette, Indiana 47907, United States.

Journal of the American Chemical Society
|August 16, 2017
PubMed
まとめ

研究者は,単純なオレフィンと1,1-ジクロルアルケンを用いて新しい触媒的還元性メチレンサイクロプロパネーション反応を開発した. この方法では,有価な合成中間物質であるストレインメチレンサイクロプロパンを効率的に合成します.

科学分野:

  • 有機化学
  • カタリシス
  • 合成方法論

背景:

  • メチレンcyclopropanesは,重要な合成ユーティリティを持つ高度にストレスのサイクル化合物です.
  • その合成にはしばしば特殊な反応剤や条件が必要である.
  • メチレンサイクロプロパンの固有の張力エネルギーは,飽和サイクロプロパンのそれより大きい.

研究 の 目的:

  • メチレンcyclopropanesの合成のための新しい触媒方法を開発する.
  • 容易に入手できる1,1-ジクロアルケンをビニリデンの前駆体として利用する.
  • 触媒的還元性メチレンサイクロプロパネーションのメカニズムを探求する.

主な方法:

  • 二核ニッケル (Ni) 触媒を用いて反応を促す.
  • 単純なオレフィンと1,1-ジクロアルケンを原料として利用する.
  • C-Cl酸化添加によるNi2 (ビニリデノイド) 中間物質の形成を調査する.

主要な成果:

  • 単純なオレフィンの触媒的還元性メチレンサイクロプロパネーションが成功しました.
  • この反応はメチレンサイクロプロパン構造に効率的なアクセスを提供します.

さらに関連する動画

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

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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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Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes
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Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

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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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  • 二核のNi触媒は,提案された中間物質を通じて変換を容易にする.
  • 結論:

    • メチレンサイクロプロパンへの新しい合成経路が確立されています.
    • 触媒システムは 有価な合成中間物質を生成するための効率的な方法を提供する.
    • Ni2 ((ビニリデノイド) 中間物質を含む提案されたメカニズムは,反応経路の洞察を提供します.