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関連する概念動画

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

8.1K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
8.1K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

7.8K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
7.8K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

2.6K
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...
2.6K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

19.7K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
19.7K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

14.2K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
14.2K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

6.9K
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.
6.9K

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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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スキャフォルディングの触媒を用いたディスタル選択型水酸化.

Candice L Joe1, Thomas P Blaisdell, Allison F Geoghan

  • 1Department of Chemistry, Merkert Chemistry Center, Boston College , Chestnut Hill, Massachusetts 02467, United States.

Journal of the American Chemical Society
|June 7, 2014
PubMed
まとめ
この要約は機械生成です。

この研究は,水酸化形成のための新しい誘導群を導入し,誘導機能の遠隔にアルデヒド形成を可能にします. この方法では,同性アルコールから選択的にδ-ラクトンを合成します.

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科学分野:

  • 有機化学 オーガニック・ケミストリー
  • カタリシス カタリシス カタリシス
  • 合成方法論 合成方法論

背景:

  • ハイドロフォーミレーションにおけるリン基基導向群は,典型的にはアルデヒド形成を近隣の炭素に導きます.
  • 新しい合成経路のための遠隔機能化を可能にする触媒システムが必要である.

研究 の 目的:

  • 設計と合成のための新しい脚立架リガンドを設計し,合成する.
  • 指揮グループから遠方の地域選択性アルデヒド形成を達成するために.
  • この方法論をδ-ラクトンの合成に適用する.

主な方法:

  • リバーシブル・コヴァレンント・ボンドで動作する新しいディレクター・グループの開発.
  • ホモアリルアルコールの水酸化過程におけるディレクティンググループの応用.
  • 地域選択性を最適化するために,基板構造の系統的な変化.

主要な成果:

  • 新規の監督グループは,遠縁炭素のアルデヒド形成を成功裏に促進しています.
  • ホモアリルアルコールのダイアステロセレクティブ水酸化反応により,選択性が高いδ-ラクトンが得られます.
  • 地域選択性はホモアリルアルコールの場合が最も高く,基質依存制御を示しています.

結論:

  • 新しい触媒システムにより,水酸化過程で遠隔機能化が可能になる.
  • この方法論は, δ-ラクトンへの選択的な経路を提供します.
  • 指示グループの設計は,特定の地域化学的結果に合わせて調整することができます.