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関連する概念動画

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...

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関連する実験動画

Updated: Jul 4, 2026

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

二対のディロジウムイミド複合体:形成,構造,アルキンサイクル添加反応性

Shin Takemoto1, Shohei Otsuki, Yasuhiro Hashimoto

  • 1Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Gakuen-cho 1-1, Naka-ku, Sakai, Osaka 599-8531, Japan. takemoto@c.s.osakafu-u.ac.jp

Journal of the American Chemical Society
|June 19, 2008
PubMed
まとめ

新しいディロジウムアミド複合体が合成され,ディロジウムイミド種を作成するために使用されました. これらのイミド種は,アルキンとサイクル添加反応を行い,新しいアザメタラサイクルを形成し,ステリカル阻害反応剤を使用して分離することができます.

さらに関連する動画

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

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

関連する実験動画

Last Updated: Jul 4, 2026

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

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

科学分野:

  • 有機金属化学 有機金属化学
  • 協調化化学について

背景:

  • ディロジウム複合体は,有機金属合成における汎用的な前駆体である.
  • イミドリンガンドは,触媒サイクルと材料科学において重要な役割を果たします.

研究 の 目的:

  • 新しいディロジウムアミド複合体を合成するために.
  • ディロジウム・イミド種の反応性を調べるために.
  • 新しい有機金属化合物とその構造を特徴付ける.

主な方法:

  • 複合合成のための塩化物の異位反応.
  • フォスフィンとアルキンによるトラッピング反応.
  • ステリー阻害反応剤によるメタテシス反応.
  • 構造的決定のためのX線結晶学.

主要な成果:

  • ディロジウムアミド複合体の合成 [ ((Cp*Rh) 2 ((mu2-NHPh)) ((mu2-X)) ].
  • ディロジウムイミド種の形成 [Cp*Rh(mu2-NPh) RhCp*].
  • サイクロアディション反応でアザメタラサイクルの生成 [Cp*Rh(mu2-eta2:eta3-R1CCR2NPh) RhCp*].
  • 不飽和イミド複合体 [Cp*Rh(mu2-NAr) RhCp*]をステリック阻害反応剤を用いて分離する.
  • 主要な中間物質と製品の構造的特徴は,X線微分法による.

結論:

  • ディルホージウムアミド複合体は,反応性ディルホージウムイミド種の効果的な前駆体である.
  • イミド種は,アルキネスとのサイクロアディションを含む多様な反応性を示す.
  • ステリック阻害は,不飽和イミド複合体を分離するための鍵です.
  • 報告された構造は,ディロジウム系における結合と反応性についての洞察を提供します.