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Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

3.2K
Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
3.2K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.4K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.4K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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

2.8K
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.
2.8K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.1K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.1K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.7K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.7K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.6K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
3.6K

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関連する実験動画

Updated: Jul 30, 2025

Unraveling Entropic Rate Acceleration Induced by Solvent Dynamics in Membrane Enzymes
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Unraveling Entropic Rate Acceleration Induced by Solvent Dynamics in Membrane Enzymes

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9.1K

溶媒選択による逆転可能なマクロサイクルからマクロサイクルへの相互変換

Fei Wang1, Xiangling Shi1, Yi Zhang1

  • 1State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, People's Republic of China.

Journal of the American Chemical Society
|May 12, 2023
PubMed
まとめ
この要約は機械生成です。

研究者は,自己組み立てのマクロサイクルのための新しいワンポット合成を開発しました. 溶媒の選択は,異なるサイズのマクロサイクル製品の形成を制御し, [1 + 1] と [2 + 2] 構造間の可逆的な相互変換を可能にします.

さらに関連する動画

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

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関連する実験動画

Last Updated: Jul 30, 2025

Unraveling Entropic Rate Acceleration Induced by Solvent Dynamics in Membrane Enzymes
09:42

Unraveling Entropic Rate Acceleration Induced by Solvent Dynamics in Membrane Enzymes

Published on: January 16, 2016

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.9K

科学分野:

  • 超分子化学
  • 有機合成
  • 材料科学

背景:

  • マクロサイクルからマクロサイクルへの相互変換は,多様な構造的可能性を提供します.
  • 異なるサイズのマクロサイクル間の制御された,可逆的な相互変換を達成することは大きな課題です.

研究 の 目的:

  • 自己組み立てのマクロサイクルのための簡単な1ポット合成を開発する.
  • 溶媒操作によるマクロサイクルサイズと相互変換の制御を調査する.

主な方法:

  • α,α'-結合オリゴピロルジアルデヒドとアルキルダイアミンの間の凝縮反応.
  • 様々な溶媒 (メタノール,エタノール,クロロフォーム,DMSO,DMF,MeCN) を使って製品の配給に影響を与える.
  • マクロサイクル製品 ([1 + 1]と [2 + 2]組) の特性

主要な成果:

  • ピリジン・ブリッジされたオリゴピロリック・ダイアルデヒド (3) とアルキル・ダイアミンは溶媒に独立して [2 + 2] マクロサイクルを容易に形成する.
  • 3を2,2'-オキシビス (イチラミン) (14) で凝縮すると,溶媒の選択に基づいて [1 + 1] または [2 + 2] のマクロサイクルが得られます.
  • 特定の溶媒 (メタノール,エタノール,クロロフォーム) は [1 + 1] 製品を好み,他の溶媒 (DMSO,DMF,MeCN) は [2 + 2] 製品を好み,しばしば沈殿物として.
  • [1 + 1] と [2 + 2] マクロサイクル間の可逆的な相互変換は,熱力学および溶解性因子によって導かれる溶媒の変化によって達成可能である.

結論:

  • 自己組み立てのマクロサイクルを合成するための汎用的なワンポット方法が確立されています.
  • 溶剤制御の可逆的なマクロサイクル相互変換が示され,構造的多様性の新しい戦略が提供されます.
  • 発見は,自己組み立てプロセスを指示する際に熱力学および溶解性パラメータの重要性を強調しています.