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関連する概念動画

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the bromine molecule...
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...
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.

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関連する実験動画

Updated: May 18, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

硫黄ベースのズウィテリオン有機触媒を用いた効率的な中程度のリングサイズのブロモラクトニゼーション.

Yi An Cheng1, Tao Chen, Chong Kiat Tan

  • 1Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.

Journal of the American Chemical Society
|September 25, 2012
PubMed
まとめ
この要約は機械生成です。

新種のズウィテリオン触媒は,触媒性ブロモラクトニゼーションを介して,オレフィン酸から中規模のラクトンを効率的に合成します. 反応は0°Cで最適で,触媒が浮き彫りにされる.

さらに関連する動画

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

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: May 18, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

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
  • カタリシス カタリシス カタリシス
  • 合成化学 合成化学とは

背景:

  • 中型ラクトンの効率的な合成は,様々な化学用途において極めて重要です.
  • ラクトン合成のための伝統的な方法は,しばしば厳しい条件や複数のステップを伴う.
  • 選択的変換のための新しい触媒システムの開発は,活発な研究分野です.

研究 の 目的:

  • 中規模のラクトンを合成するための効率的な触媒性ブロモラクトニゼーション方法について報告する.
  • この変換におけるズウィテリオン触媒の使用を調査する.
  • ブロモラクトニゼーションの効率に対する反応温度の影響を探求する.

主な方法:

  • 長い鎖のオレフィン酸の触媒的ブロモラクトニゼーションにズウィットリオン触媒を用いた.
  • ステキオメトリックハロゲン源としてN-ブロモスクシニミドを使用した.
  • 効率を評価するために,異なる温度 (0°Cと室温) で反応を行った.

主要な成果:

  • 長鎖オレフィン酸から中型ラクトンの効率的な合成を達成した.
  • ズウィテリオン触媒は,ブロモラクトニゼーション反応を促進する上で高い有効性を示しました.
  • 反応効率は,室温と比較して0°Cではかなり高かった.

結論:

  • ブロモラクトニゼーションのための新しい効率的な触媒システムが開発されました.
  • ズウィテリオン触媒は,中規模のラクトンを合成するのに有効です.
  • ズウィテリオン触媒の温度依存は反応効率に影響し,低温を好む.