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相关概念视频

Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

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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...
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

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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.
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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

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Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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利用区域和立体选择性C ((sp3) -H功能化乙烯训练物流回归分类模型来预测位置选择性偏差

Yannick T Boni1, Ryan C Cammarota2, Kuangbiao Liao1

  • 1Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, United States.

Journal of the American Chemical Society
|August 17, 2022
PubMed
概括
此摘要是机器生成的。

这项研究证明了使用碳中间体的基乙烯的位点和立体选择性C-H功能化. 一个机器学习模型预测功能化部位, 帮助复杂的分子合成.

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科学领域:

  • 有机化学
  • 催化剂
  • 合成方法

背景情况:

  • 乙烯的C-H功能化提供了一个战略性的合成途径.
  • 碳插入提供了一种有效的C-H键激活方法.

研究的目的:

  • 在不同位置实现位点和立体选择性C ((sp3) -H功能化.
  • 开发C-H功能化地点选择的预测模型.
  • 为了实现中乙烯的后期功能化和脱对称.

主要方法:

  • 用于C-H插入反应的捐赠/接受碳中间体.
  • 使用具有明显选择性的催化剂 (Rh2 ((R-TCPTAD) 4和Rh2 ((S-2-Cl-5-BrTPCP) 4).
  • 开发了一个逻辑回归机器学习模型来预测功能化站点.

主要成果:

  • 在α,γ,δ和距离位置实现了位点和立体选择性C(sp3)-H功能化.
  • 在产品形成方面表现出良好的二元控制和反抗控制.
  • 成功地应用了脱对称的方法.
  • 验证了用于预测主要C-H功能化的机器学习模型.

结论:

  • 开发的碳素诱导的C-H功能化是乙烯的多功能策略.
  • 预测机器学习模型有助于指导复杂分子的合成策略.
  • 该方法方便后期功能化和脱对称化,增强合成效用.