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Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

3.6K
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...
3.6K
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

5.2K
The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
5.2K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

4.9K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
4.9K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

7.7K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
7.7K
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

9.5K

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
9.5K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.0K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.0K

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関連する実験動画

Updated: May 23, 2025

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
09:37

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

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塩基複合体によって催化されるメタンベリル化

Josef T Boronski1, Agamemnon E Crumpton2, Job J C Struijs2

  • 1Molecular Sciences Research Hub, Department of Chemistry, Imperial College London, 82 Wood Lane, White City, London W12 0BZ, U.K.

Journal of the American Chemical Society
|March 11, 2025
PubMed
まとめ
この要約は機械生成です。

研究者は新しいベリル化反応を用いて,メタンの挑戦的な触媒的機能化を達成しました. 光化学的条件と特定のマンガンまたはレニウム触媒により,強いC−H結合がメタンとベンゼンに変換された.

さらに関連する動画

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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関連する実験動画

Last Updated: May 23, 2025

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

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科学分野:

  • 有機金属化学
  • カタリシス
  • 写真化学

背景:

  • メタンの機能化は,非極性性質と強いC−H結合により困難である.
  • 均質な触媒は潜在的な経路を提供しているが,重大な障害に直面している.

研究 の 目的:

  • メタンとベンゼンのC−H結合の触媒的機能化のための新しい方法を開発する.
  • C−H結合の活性化におけるベリル化の役割を調査する.

主な方法:

  • CpMn (CO) 3またはCp*Re (CO) 3の触媒量 (10mol %) を利用した光化学反応.
  • トランス・ビス・ベリリル・マンガネス・レニウム複合体を含む反応中間物の分離と特徴付け.
  • 反応メカニズムを解明するための量子化学計算.

主要な成果:

  • メタンとベンゼンのC-H結合を光化学条件下でCpBeBeCpを用いてC-BeとH-Be結合に変換する.
  • マンガンとレニウムベリル化中間物の分離
  • メタンの機能化に不可欠なベリリルリガンドの σ ドナーおよびルイス酸性特性の特定.

結論:

  • CpMn (CO) 3とCp*Re (CO) 3は,光化学的条件下でメタンとベンゼンのベリル化を触媒化する.
  • ベリリルリガンドのユニークな電子特性により,C-H結合の活性化が容易になる.
  • この研究は,惰性炭化水素の均質な触媒機能化のための新しい戦略を提示しています.