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関連する概念動画

Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.5K
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...
2.5K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.7K
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...
2.7K
Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

4.9K
The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
4.9K
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

4.3K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
4.3K
Alkali Metals03:06

Alkali Metals

25.1K
Group 1 elements are soft and shiny metallic solids. They are malleable, ductile, and good conductors of heat and electricity. The melting points of the alkali metals are unusually low for metals and decrease going down the group, while the density increases going down the group with the exception of potassium (Table 1).
Table 1: Properties of the alkali metals
25.1K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

11.1K
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.
11.1K

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関連する実験動画

Updated: Feb 22, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
09:45

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

Published on: November 12, 2016

32.1K

アルカリ金属アルコキシドが,有機原発反応を起こす方法

Seb Tyerman1, Kenneth F Clark1, Alexander J Stewart1

  • 1Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, U.K.

Journal of the American Chemical Society
|February 20, 2026
PubMed
まとめ

アルカリ金属アルコシドは,電子の移転ではなく,ベンジンの中間物質を通じて,ラジカル化学を開始します. この研究は,複数のベンジンタイプの同時形成と新しいメチル化メカニズムを明らかにしています.

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

Published on: April 22, 2016

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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

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関連する実験動画

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A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
09:45

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

Published on: November 12, 2016

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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

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

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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

11.7K

科学分野:

  • 有機化学 オーガニック・ケミストリー
  • 反応メカニズム 反応メカニズム

背景:

  • アルカリ金属アルコシドは,アリルハリドの水解塩素化と結合反応を促進することが知られている.
  • 以前は,これらの反応はアルコキシドから電子の移転によって形成されるアリルラジカル中間物質を含むと考えられていた.

研究 の 目的:

  • アルカリ金属アルコキシドがアリルハリドと反応するメカニズムを調査する.
  • 電子の移転またはデプロトネーションが激素化学を始動するかどうかを決定する.

主な方法:

  • デウテリウム同位体の研究は,反応機構を調査するために使用されました.
  • 様々なアルカリ金属アルコキシド,例えば三酸化カルシウムを含むアルコキシドで反応を行った.

主要な成果:

  • この研究は,電子伝送機構を否定し,デプロトネーションが,過激な化学反応を誘発するベンジン中間産物につながることを示しています.
  • オーソ-,メタ-,パラ-,およびリモートベンジンの同時形成が観察されました.
  • テート・ブトオキシドから派生したメチルラジカルを介してアレンをメチル化する新しいメカニズムが特定されました.

結論:

  • アリルラジカルを形成する電子移転を含む確立されたメカニズムは間違っている.
  • ベンジンの中間物質は,アルカリ金属アルコキシドによって開始される過激化学の鍵です.
  • この発見は,ベンジン形成とアルコキシド由来の過激化学に関する新しい洞察を明らかにします.