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関連する概念動画

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,...
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic rearrangements are...
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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.
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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.

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関連する実験動画

Updated: Jun 9, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

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効率的なマクロサイクライゼーションは,分子間非共性π-カチオン/アレン相互作用を用いた構成制御によって達成される.

Philippe Bolduc1, Alexandre Jacques, Shawn K Collins

  • 1Université de Montréal, Département de Chimie, C.P. 6128 Station Downtown, Montréal, Québec, H3C 3J7, Canada.

Journal of the American Chemical Society
|August 27, 2010
PubMed
まとめ

キノリニウム塩3は,オレフィン転化またはグラザー-ヘイ結合を用いた硬いサイクロファンの合成のためのマクロサイクリングを効果的に促進します. この形状制御要素 (CCE) は簡単に合成され,修正され,回収できます.

さらに関連する動画

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
16:24

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water

Published on: August 2, 2012

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
05:48

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

関連する実験動画

Last Updated: Jun 9, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
07:11

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Published on: September 28, 2022

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
16:24

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water

Published on: August 2, 2012

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
05:48

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

科学分野:

  • 有機化学 オーガニック・ケミストリー
  • 合成化学 合成化学とは

背景:

  • マクロサイクリングは,複雑な分子構造の合成に不可欠です.
  • 伝統的な方法では,硬いサイクロファンを効率的に形成するのに苦労することが多い.

研究 の 目的:

  • 新しい添加物,キノリニウム塩3をコンファーマーションコントロールエレメント (CCE) として導入する.
  • マクロサイクライゼーション反応を促進するCCEの有用性を実証する.

主な方法:

  • オレフィンメタテシス反応でキノリニウム塩3を使用する.
  • グラザー-ヘイ結合反応でキノリニウム塩3を使用しています.
  • その結果生じる硬いサイクロファンを特徴づける.

主要な成果:

  • キノリニウム塩3は,硬いサイクロファンのマクロサイクリング率を大幅に高めます.
  • この添加物は,そうでなければ失敗する反応におけるサイクル化を促進します.
  • CCEは簡単に合成され,改変され,濾過によって回収できます.

結論:

  • キノリニウム塩3は,マクロサイクリングのための多用途で効果的な添加物です.
  • このアプローチは,硬いサイクロファンを構築するための新しい戦略を提供します.
  • 開発された添加物は,合成と浄化において実用的な利点を提供します.