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Related Concept Videos

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.
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.
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).
Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

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Related Experiment Video

Updated: May 7, 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

Gold-catalyzed oxidative cycloadditions to activate a quinoline framework.

Deepak B Huple1, Satish Ghorpade, Rai-Shung Liu

  • 1Department of Chemistry, National Tsing Hua University, Hsinchu, 30013 (Taiwan), Fax: (+886) 3-5711082.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 17, 2013
PubMed
Summary

Gold catalysts facilitate a novel oxidative cycloaddition reaction with dienynes and quinoline oxides. This process generates valuable compounds with high stereospecificity through a unique catalytic activation mechanism.

Keywords:
catalysiscycloadditiongoldoxidative cyclizationstereoselectivity

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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Facile Preparation of 4-Substituted Quinazoline Derivatives

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Facile Preparation of 4-Substituted Quinazoline Derivatives
11:51

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Reaction Mechanisms

Background:

  • Gold catalysis is a rapidly growing field in organic synthesis.
  • Oxidative cycloaddition reactions are important for constructing complex molecular architectures.
  • Quinoline derivatives serve as versatile building blocks in medicinal chemistry.

Purpose of the Study:

  • To develop a novel gold-catalyzed oxidative cycloaddition reaction.
  • To investigate the mechanism of this transformation.
  • To explore the utility of 8-alkylquinoline oxides in catalysis.

Main Methods:

  • Reaction of 3,5- and 3,6-dienynes with 8-alkylquinoline oxides.
  • Gold(I) or Gold(III) catalysis.
  • Stereochemical analysis to determine stereospecificity.

Main Results:

  • Achieved high stereospecificity in the oxidative cycloaddition.
  • Identified α-carbonyl pyridinium ylides as key intermediates.
  • Demonstrated catalytic activation of the quinoline framework.

Conclusions:

  • The developed gold-catalyzed reaction provides an efficient route to complex molecules.
  • The reaction proceeds via a concerted [3+2]-cycloaddition mechanism.
  • This work expands the scope of gold catalysis in organic synthesis.