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相关概念视频

Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
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.
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...
C–C Bond Formation: Aldol Condensation Overview01:10

C–C Bond Formation: Aldol Condensation Overview

Aldol condensation is an important route in synthetic organic chemistry used to generate a new carbon–carbon bond under basic or acidic conditions. The aldol condensation reaction presented in Figure 1 constitutes an aldol addition reaction followed by the dehydration process.
C–C Bond Cleavage: Retro-Aldol Reaction00:57

C–C Bond Cleavage: Retro-Aldol Reaction

The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.

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相关实验视频

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

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

Published on: June 20, 2014

一种轻微的C-O键形成,由氧复合物催化.

Benjamin D Sherry1, Alexander T Radosevich, F Dean Toste

  • 1Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley 94720, USA.

Journal of the American Chemical Society
|June 6, 2003
PubMed
概括

一种新的催化方法使得能够轻度和区域选择性合成甲基乙烯. 这种高效的过程使用氧复合物形成碳氧键,耐受多种功能组.

科学领域:

  • 有机化学 有机化学
  • 催化剂是一种催化剂.
  • 合成方法论 合成方法论

背景情况:

  • 甲基乙烯是有价值的合成中间体.
  • 现有的合成方法通常需要恶劣的条件或先前的激活步骤.

研究的目的:

  • 开发一种温和和区域选择性方法来合成基乙烯.
  • 为了利用耐空气和耐湿性催化剂形成C-O键.

主要方法:

  • 甲基酒精与各种酒精的合.
  • 使用氧复合物 ((dppm) ReOCl3) 的催化.
  • 不需要先前激活propargyl酒精或核爱体的deprotonation.

主要成果:

  • 在温和条件下成功地进行了propargyl的区域选择性合成.
  • 氧催化剂显示出对空气和水分的耐受性.
  • 宽泛的功能组耐受性,包括烯化物,烯,,乙,初级基化物和合.
  • 酒精在其他电友上具有优越的排位.

结论:

  • 已经建立了一种新的,温和的,区域选择性的催化方法来合成甲基以太.

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  • 氧复合物为sp3碳氧键的形成提供了高效和强大的催化剂.
  • 该方法对各种功能组的耐受性和化学选择性使其在有机合成中广泛适用.