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Preparation of Epoxides03:00

Preparation of Epoxides

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 peroxy acids to...
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

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...
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

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...
Sharpless Epoxidation02:57

Sharpless Epoxidation

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...
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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

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...

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関連する実験動画

Updated: Jun 7, 2026

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
09:08

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes

Published on: February 27, 2017

二金属コバルト触媒を用いたエナチオセレクティブエポキシドポリメリゼーション.

Renee M Thomas1, Peter C B Widger, Syud M Ahmed

  • 1Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, United States.

Journal of the American Chemical Society
|November 4, 2010
PubMed
まとめ

新しいコバルト触媒は,エポキシドの急速で高度にステレオ選択的なポリメリゼーションを可能にし,イソタキシカルポリエーテルを生成します. この画期的な発見は,優れた熱特性を持つポリマーを合成するための新しい方法を提供します.

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

Published on: November 21, 2017

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties
10:16

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

Published on: January 8, 2016

関連する実験動画

Last Updated: Jun 7, 2026

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
09:08

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes

Published on: February 27, 2017

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

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties
10:16

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

Published on: January 8, 2016

科学分野:

  • ポリマー化学のポリマー化学について
  • 有機金属化学 有機金属化学

背景:

  • エナチオセレクティブポリメリゼーションは,ステレオレギュラーポリマーの生成に不可欠です.
  • ステレオセレクティブエポキシドポリメリゼーションのための効率的な触媒の開発は,依然として課題です.

研究 の 目的:

  • エナチオセレクティブエポキシドポリメリゼーションのための高度に活性なエナチオピュアバイメタリックコバルト複合体を調査する.
  • 高率とステレオ選択性のためのポリメリゼーション条件を最適化するために.
  • ラセミのエポキシドからアイソタクティックポリエッターの合成を調査する.

主な方法:

  • 高活性なエナチオピュアバイメタリックコバルト複合体を使用した.
  • 様々な単一置換エポキシドのエナチオセレクティブポリメリゼーションを行いました.
  • 高いステレオ選択性 (s-ファクター > 50,一部 > 300) を達成するために反応条件を最適化.
  • イソタキシカルポリエーテルを準備するために,ラセミック触媒を使用した.

主要な成果:

  • 一連のエポキシドに対して,高いポリメリゼーション率とステレオ選択性を達成した.
  • 高いイソタクシー性 (mmトライアード>95%,一部>98%) を有するポリマーを製造した.
  • ラセミック触媒を用いて,定量的収量で合成されたイソタクティックポリエーテル.
  • 結果となるイソタキシカルポリエーテルには,高い融解温度 (T ((m)) が実証されています.

結論:

  • バイメタリックコバルト複合体は,エポキシドの急速なエナンチオセレクティブポリメリゼーションに非常に効果的です.
  • この研究は,ラセミックエポキシドから多様な,高度にイソタキシ性ポリエーテルを迅速に合成した最初の報告を提示しています.
  • 開発された方法は,望ましい熱特性を持つステレオレギュラーポリエーテルへの貴重な経路を提供します.