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Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

7.1K
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
7.1K
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

8.2K
Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
8.2K
Preparation of Epoxides03:00

Preparation of Epoxides

7.4K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
7.4K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

5.6K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
5.6K
Sharpless Epoxidation02:57

Sharpless Epoxidation

3.8K
The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
3.8K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

2.5K
Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
2.5K

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関連する実験動画

Updated: May 31, 2025

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

8.0K

酸性の逆転は,バイプロトン化合物からのエポキシドのサイト固有のリング開きポリメリゼーションを可能にします.

Urška Češarek1,2, Lijun Liu3, Qiyi Chen3

  • 1Department of Polymer Chemistry and Technology, National Institute of Chemistry, Hajdrihova 19, 1000 Ljubljana, Slovenia.

Journal of the American Chemical Society
|January 22, 2025
PubMed
まとめ
この要約は機械生成です。

保護されたアミノアルコールを用いて アミノ機能化されたポリエーテルを合成する 新しい方法を開発しました この有機触媒的アプローチはポリメリゼーションを効率的に制御し,高度なポリマー材料を作るためのアミンの機能性を保持します.

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

Published on: December 16, 2022

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

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関連する実験動画

Last Updated: May 31, 2025

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

8.0K
Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
08:12

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

3.2K
Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

2.9K

科学分野:

  • ポリマー化学
  • 有機合成
  • 材料科学

背景:

  • ポリエッターは広く使用されていますが,アミンの機能を組み込むことは困難です.
  • エポキシドのアニオン環開きポリメリゼーション (ROP) は,その核愛性のためにアミン群を保護する必要があります.
  • 既存の方法はしばしば厳しい条件や 複雑なグループ保護戦略を含みます

研究 の 目的:

  • アミノ機能化されたポリエッターの 簡素化された合成を開発する.
  • N-カルバメートで保護されたアミノアルコールをエポキシードROPのイニシアターとして使用する.
  • アミンの機能性を保ちながら制御されたポリメリゼーションを達成する.

主な方法:

  • エポキシドのアニオンリング開封ポリメリゼーション (ROP)
  • N-カルバマートで保護されたアミノアルコールをイニシアターとして使用する.
  • ルイス酸過剰の2つのコンポーネントの有機触媒システムを使用しています.

主要な成果:

  • エポキシドの効率的なROPは,有機触媒システムを使用して達成されました.
  • カルバマート保護群は,ポリメリゼーションを通して無傷のまま残った.
  • 合成されたポリプロピレン酸化物とポリエチレン酸化物は,制御されたモラ質量と低分散性を有していた.
  • アミノ機能は保存され,ハイブリッドブロックコポリマーを作成するために使用されました.

結論:

  • アミノ機能化されたポリエーテルを合成するための堅牢で効率的な方法が確立されました.
  • オーガノ触媒システムは,酸性逆転効果によって,サイト固有のポリメリゼーションを可能にします.
  • このアプローチは,ポリペプトイドベースのハイブリッドブロックコポリマーなどの高度なポリマーアーキテクチャの作成を容易にする.