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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

2.9K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Thermal Sigmatropic Reactions: Overview01:16

Thermal Sigmatropic Reactions: Overview

2.2K
Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in...
2.2K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

2.2K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
2.2K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

8.7K
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.
8.7K
Prochirality02:05

Prochirality

4.0K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

10.0K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
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Updated: Sep 16, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

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

Published on: November 9, 2019

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[2,3]-Sigmatropic重新排列与[1.1.1]螺旋进行了重新排列.

Suparnak Midya1, Aksar Ali1, Durga Prasad Hari2

  • 1Department of Organic Chemistry, Indian Institute of Science, Bangalore, India.

Nature communications
|July 7, 2025
PubMed
概括

[1.1.1]作为一种新型[2,3]-sigmatropic重组的碳素前体,有效地形成基或基甲基环. 这种方法还可以合成有价值的二[2.1.1]hexanes,宝贵的二异构体.

科学领域:

  • 有机化学 有机化学
  • 合成方法论 合成方法论
  • 碳烯化学 碳烯化学

背景情况:

  • 已确定的 [1.1.1] 螺旋反应性涉及桥梁C-C键上的加法反应.
  • 形成双环[1.1.1]坦衍生物是一个已知的结果.
  • 对于利用 [1.1.1] 烯作为碳烯前体的方法有限.

研究的目的:

  • 开发一种使用[1.1.1]propellane的新[2,3]-sigmatropic重排.
  • 为了获得基化或基化甲基环butanes.
  • 探索在合成替代双环[2.1.1] 六的后续应用.

主要方法:

  • [2.3]-sigmatropic对[1.1.1]propellane与propargyl和基硫化物/化物进行重新排列.
  • 光催化激素级联循环化用于双循环[2.1.1] 六合成.
  • 密度函数理论 (DFT) 计算以阐明反应机制.

主要成果:

  • 效率高且可扩展的基化/基化甲基环素合成.
  • 反应在温和条件下进行,具有广泛的功能组耐受性.
  • 成功合成替代的双环[2.1.1] 六,潜在的基生物异构剂.

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Last Updated: Sep 16, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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  • DFT计算表明一个铜结合的五成员过渡状态.

    • 结论:

    • 已经建立了一个使用[1.1.1]烯作为碳基前体的新合成途径.
    • 该方法提供了获取有价值的甲环butan和双环[2.1.1] 六支架.
    • 开发的双环[2.1.1]衍生物是药物发现的有希望的生物异构剂.