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関連する概念動画

Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

3.4K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
3.4K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

8.7K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
8.7K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

14.3K
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...
14.3K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

1.9K
Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
1.9K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.1K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.1K
Radical Formation: Addition00:47

Radical Formation: Addition

1.7K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
1.7K

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関連する実験動画

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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挫折した根のペアを用いた地域選択的アリファティックC-H機能化

Zhipeng Lu1, Minsoo Ju1, Yi Wang1

  • 1Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY, USA.

Nature
|July 5, 2023
PubMed
まとめ

フラストラテッド・ラジカル・ペア (FRP) は,活性化されていない結合を割ることで,C-H結合の機能化を可能にします. ドナー構造を調整することで,異なるC−H結合に対する反応性を制御し,新しい合成の可能性を提供できます.

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科学分野:

  • 有機金属化学
  • ラジカル・ケミストリー
  • 有機合成

背景:

  • フレストラテッド・ルイス・ペア (FLP) は小分子をヘテロリート経路で活性化させる.
  • FLPは単一の電子の移転によって 根幹のペアを形成することが示されています
  • フラストラテッド・ラジカル・ペア (FRP) は,限られた合成用途を持つ安定したラジカルである.

研究 の 目的:

  • 新種のFRPを用いてC ((sp3) -H結合の機能化を実証する.
  • 化学合成における反応剤としてのFRPの可能性を調査する.
  • FRPの反応性と地域選択性を調査する.

主な方法:

  • ディシラジドドナーとN-オクソアンモニアム受容体からFRPを生成する.
  • 活性化されていないC-H結合の割れにFRPを適用する.
  • 反応における根素対の役割を解明するメカニズム研究.

主要な成果:

  • アミノキシル化製品を生成するC ((sp3) -H結合の機能化に成功した.
  • ドナー構造を改変することによって制御された地域選択性を実証する.
  • 暫定的および永続的なラジカルペアの形成と関与を支持する証拠.

結論:

  • ディシラジドドナーとN-オキシアモニウム受容体から生成されたFRPは,C-H結合の機能化に有効である.
  • FRPの反応性は,主,二次,または三次C-H結合をターゲットに調整することができます.
  • この研究により 挫折したラジカルペアの 合成的有用性が拡大される.