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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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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.
7.7K
Preparation of Epoxides03:00

Preparation of Epoxides

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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
9.6K
Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

13.3K
In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
13.3K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

3.1K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.8K
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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Updated: Mar 9, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Oxidative Azo-Ene Cyclization.

Nolwenn Derrien1, James S Sharley1, Aleksandr E Rubtsov1,2

  • 1Department of Chemistry, Loughborough University , Loughborough, Leicestershire LE11 3TU, U.K.

Organic Letters
|December 23, 2016
PubMed
Summary
This summary is machine-generated.

A new catalytic method enables efficient synthesis of cyclic carbamates from hydrazinedicarboxylates. This reaction creates versatile compounds with an alkene group for further chemical modifications.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Cyclic carbamates are important structural motifs in medicinal chemistry.
  • Efficient synthetic routes to functionalized cyclic carbamates are highly sought after.

Purpose of the Study:

  • To develop an expedient catalytic oxidative azo-ene cyclization procedure.
  • To synthesize a diverse range of cyclic carbamate derivatives.

Main Methods:

  • Catalytic oxidative azo-ene cyclization reaction.
  • Utilized allylic and homoallylic 1,2-hydrazinedicarboxylates as substrates.

Main Results:

  • Successfully synthesized various cyclic carbamate derivatives.
  • The products contain an appended alkene fragment.
  • The appended alkene allows for further functionalization.

Conclusions:

  • The reported method provides an efficient route to valuable cyclic carbamate scaffolds.
  • The synthesized compounds serve as versatile building blocks for further chemical transformations.