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Updated: Jul 14, 2026

Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations
13:09

Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

Published on: January 4, 2018

ルテニウム (((II) 触媒化 [2 + 2 + 2] サイクロアディションで1,6-ダイネとトリカルボニル化合物が結合する

Yoshihiko Yamamoto1, Hideyuki Takagishi, Kenji Itoh

  • 1Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan.

Journal of the American Chemical Society
|June 13, 2002
PubMed
まとめ

ルテニウム触媒により,非対称な1,6-ダイネがトリカルボニル化合物と反応し,ディエノンを形成します. その後の分子内マイケルの加算により,複雑なビサイクロ[3.3.0]オクテノンの誘導体が得られます.

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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.
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[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.
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Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)

α,β-Unsaturated carbonyl compounds with two electrophilic sites, the carbonyl carbon, and the β carbon, are susceptible to nucleophilic attack via two modes: conjugate or 1,4-addition and direct or 1,2-addition.
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are formed faster owing to...
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Cycloaddition Reactions: MO Requirements for Thermal Activation

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Cycloaddition Reactions: MO Requirements for Photochemical Activation

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