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関連する概念動画

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.
[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.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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...
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.

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関連する実験動画

Updated: Jun 1, 2026

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

鉄で触媒化された分子間 [2π+2π]サイクル添加.

Sarah K Russell1, Emil Lobkovsky, Paul J Chirik

  • 1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.

Journal of the American Chemical Society
|May 24, 2011
PubMed
まとめ

ビス (((イミノ) ピリジンの鉄複合体は,エチレンとブタジエンの [2π + 2π] サイクル添加を触媒化する. 鉄メタルサイクルの中間物質が分離され,触媒機構とサイクロメタレーション経路の洞察を明らかにしました.

科学分野:

  • 有機金属化学 有機金属化学
  • カタリシス カタリシス カタリシス
  • オーガニック・シンセシス オーガニック・シンセシス

背景:

  • ビス・イミノ・ピリジン・リガンドは,協調化学における多用途の支架である.
  • 鉄複合体は,貴金属触媒の持続可能な代替品としてますます研究されています.
  • 窒素の固定とC−C結合の形成は,触媒の重要な課題である.

研究 の 目的:

  • サイクロアディション反応におけるビス・イミノ・ピリジン・鉄・ダイナトロゲン化合物の触媒活性を調査する.
  • エチレンとブタジエンの分子間 [2π + 2π] サイクル添加のメカニズムを解明する.
  • 触媒サイクルにおける主要な中間物質を特定し,特徴づけること.

主な方法:

  • ビス・イミノ・ピリジンの合成と特徴付け 鉄二酸化窒素複合体.
  • エチレンとブタジエンのサイクル添加のための触媒試験.
  • ステキオメトリック反応は,反応中間物質を分離し,研究するために行われる.
  • 反応経路を調査するためのデウテリウムラベリングの研究.

主要な成果:

  • 鉄複合物 ((iPr) PDI) Fe (((N2) 2) と [ (((Me) PDI) Fe (((N2) ]2 ((μ2-N2) は [2π + 2π]サイクル添加を効率的に触媒化する.

さらに関連する動画

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron

Published on: August 12, 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

関連する実験動画

Last Updated: Jun 1, 2026

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
07:56

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron

Published on: August 12, 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

  • 鉄メタルサイクルの中間物質が分離され,触媒的に活性であることが示されました.
  • メタロサイクルからダイネ誘発のC-C還元性の除去が観察されました.
  • デウテリウムラベリングは,リガンドアリル置換物の競争性サイクロメタライゼーションを明らかにした.

    • 結論:

    • ビスミノピリジン鉄複合体は,ビニルサイクロブタン合成の効果的な触媒である.
    • 触媒サイクルは,鉄金属サイクルの中間物質が,還元性除去を受けることを含む.
    • リンガンドサイクロメタレーションは,触媒作用の際に競合する経路である.