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関連する概念動画

Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.3K
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 stereochemistry.
9.3K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

16.0K
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...
16.0K
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

11.5K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
11.5K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
5.3K
SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

10.1K
This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
10.1K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

9.4K
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.
9.4K

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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動的に決定されたステレオ選択性における結合記憶

Vladislav A Roytman1, Shengfei Jin2, Vu T Nguyen2

  • 1Department of Chemistry , Texas A&M University , P.O. Box 30012, College Station , Texas 77842 , United States.

Journal of the American Chemical Society
|December 20, 2019
PubMed
まとめ
この要約は機械生成です。

サイクロヘキセンの炭酸性環収縮は異常な選択性を示し,単一の移行状態から逆転と保持製品の両方を形成する. この選択性は,反応ダイナミクスにおける新しい結合と古い結合の異なる行動から生じる.

さらに関連する動画

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
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科学分野:

  • 有機化学
  • 反応ダイナミクス
  • ステレオ化学

背景:

  • 炭水化物反応は炭水化物化合物の合成に不可欠である.
  • サイクロヘキセンの誘導体は,ユニークなメカニズムでリング収縮反応を経験する.
  • 協調反応におけるステレオ選択性の理解は,産物形成を制御する上で鍵となる.

研究 の 目的:

  • サイクロヘキセンのカルボボラティブリング収縮で観察された異常な選択性を調査する.
  • この反応におけるステレオ化学的結果の動的起源を解明する.
  • 計算経路と実験的なプロダクト比を相関させる

主な方法:

  • 動的軌道を用いた反応動態の計算モデル化.
  • 移行状態の構造とエネルギープロフィールの分析
  • 計算された製品分布を実験データと比較する.

主要な成果:

  • カーボボラティブ・リングの収縮は主に逆転産物をもたらしますが,重要な保持産物も発生します.
  • 逆転と保持の両方が同じ移行状態から発生します.
  • 動的軌道は,観察された実験製品の比率を正確に予測します.

結論:

  • この異常な選択性は,初期債券移行後の新規債券と既存の債券のダイナミックな非同等性によるものである.
  • 反応のダイナミクスは,ステレオ化学的結果を決定する上で重要な役割を果たします.
  • この研究は,複雑な有機変異における選択性の制御に関する洞察を提供します.