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相关概念视频

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
Acid Halides to Alcohols: Grignard Reaction01:15

Acid Halides to Alcohols: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...

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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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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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乙烯基化物通过催化三元合的形成.

Barry M Trost1, Anthony B Pinkerton

  • 1Department of Chemistry, Stanford University, Stanford, California 94305, USA. bmtrost@stanford.edu

Journal of the American Chemical Society
|June 20, 2002
PubMed
概括

催化剂能够从和中选择性合成E/Z乙烯基化物. 溶剂的选择决定了异构体的形成:极性溶剂倾向于E异构体,而非极性溶剂倾向于Z异构体,提供了多功能合成路径.

科学领域:

  • 有机金属化学 有机金属化学
  • 催化剂是一种催化剂.
  • 合成有机化学 合成有机化学

背景情况:

  • 催化合反应对于C-C键的形成至关重要.
  • 乙烯基化物是多功能合成中间体.

研究的目的:

  • 研究催化三元合的,和化物离子的三元合.
  • 优化反应条件,用于选择性合成E-和Z-乙烯基化物.
  • 探索开发的方法论的范围和局限性.

主要方法:

  • 系统地优化反应参数,包括催化剂,共催化剂,溶剂和化物源.
  • 用于合成乙烯基的循环二烯基 (II) 复合物.
  • 使用不同的 (II) 催化剂和合成乙烯基化物的条件.
  • 研究的基质范围包括功能化的基因.

主要成果:

  • 使用特定的催化剂,共催化剂和极性溶剂 (DMF) 实现了E-乙烯化物的选择性合成.
  • 使用特定的催化剂,共催化剂和非极性溶剂 (乙) 实现了Z-乙烯基化物的选择性合成.
  • 证明溶剂极性是控制E/Z选择性的关键.
  • 观察到增强的Z-选择性与propargylic替代品和完整的Z-选择性与乙烯.

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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  • 来自基质的已识别的二或循环赫森产品,含有绑定的酒精或.

    • 结论:

    • 开发了高效的催化方法,用于合成各种E-和Z-乙烯基化物.
    • 确立了溶剂极性和乙烯化异构体选择性之间的明显相关性.
    • 突出了乙烯基化物作为前体在随后的转化过程中的实用性,如苏子基合和α-基和环二的合成.