Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

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

[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.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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.

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

Halogenation of Alkenes

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

Diels–Alder Reaction: Characteristics of Dienes

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,...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Biocompatible Sulfobetaine Polymer-Artemisinin Conjugates Inducing Ferroptosis in Cancer Cells: Synthesis by Mechanochemical Solid-State Polymerization and Characterization.

Macromolecular rapid communications·2026

Same author

Characterization of Mechanochemical Solid-State Polymerization for Development of Sulfobetaine Polymer-Drug Conjugates: Design and Synthesis of Artemisinin-Conjugated Novel Methacrylamide Derivatives.

Chemical & pharmaceutical bulletin·2026

Same author

Low-Viscosity Concentrated Lithium Chloride Solution with Unsymmetrical Ditopic Receptors in Organic Solvents.

Chemphyschem : a European journal of chemical physics and physical chemistry·2025

Same author

Structure of Ion Pair Receptor Combined with Li<sup>+</sup>Cl<sup>-</sup> in Concentrated Acetonitrile Solutions Studied by Neutron Diffraction with <sup>6</sup>Li/<sup>7</sup>Li Isotopic Substitution Method.

The journal of physical chemistry. B·2024

Same author

Unlocking the Use of LiCl as an Inexpensive Salt for Lithium-Ion Batteries with a Novel Anion Receptor.

Materials (Basel, Switzerland)·2024

Same author

Dextran-based nanoparticles with 5-FU-conjugated polymethacrylate segments for drug delivery: Synthesis of amphiphilic graft copolymers by mechanochemical solid-state polymerization and characterization.

International journal of biological macromolecules·2024

Same journal

A General Photocatalytic Decarboxylative Hydrogenation of Carboxylic Acids in Batch and Flow under Metal-Free Conditions.

Organic letters·2026

Same journal

Direct Access to Sulfonamidated-1,4-Benzoquinones via Sulfonamidation of Aryl Alcohol-Derived Quinone Monoacetals.

Organic letters·2026

Same journal

Photo/Cerium Co-Catalyzed Hydroalkylation of Alkynes Via Decarboxylative Ring-Opening of Cyclic Carboxylic Acids.

Organic letters·2026

Same journal

Electrochemical Dehydroxylative Thiolation of Alkyl Alcohols with Disulfides.

Organic letters·2026

Same journal

Molybdenum-Catalyzed Intramolecular Deoxygenative Annulation of 2-(Formamido)aryl Ketones to Access 3-Monosubstituted Oxindoles.

Organic letters·2026

Same journal

Modular Synthesis of Spiroisochromans with Spiro Quaternary Carbon Centers Via TBAT-Promoted Multicomponent Cascade Reactions.

Organic letters·2026

See all related articles

Search research articles

Related Experiment Video

Updated: Mar 17, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

Silanediol-Catalyzed Chromenone Functionalization.

Andrea M Hardman-Baldwin¹, Michael D Visco¹, Joshua M Wieting¹

¹Department of Chemistry and Biochemistry, The Ohio State University , 100 West 18th Avenue, Columbus, Ohio 43210, United States.

Organic Letters

|July 26, 2016

Summary

This summary is machine-generated.

Sildeniol catalysts enable enantioselective addition of silyl ketene acetals to benzopyrylium triflates. This method advances chromanone and tetrahydroxanthone synthesis, yielding valuable bioactive compounds.

More Related Videos

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

Related Experiment Videos

Last Updated: Mar 17, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

Area of Science:

Organic Chemistry
Catalysis
Asymmetric Synthesis

Background:

Benzopyrylium triflates are key intermediates in heterocyclic synthesis.
Enantioselective functionalization of chromenones remains a synthetic challenge.
Carbonyl-containing nucleophiles offer versatile synthetic pathways.

Purpose of the Study:

To develop a novel enantioselective method for functionalizing benzopyrylium triflates.
To explore the use of silanediol catalysts in asymmetric synthesis.
To demonstrate the utility of this reaction in synthesizing bioactive molecules.

Main Methods:

Silylanediol-catalyzed addition reaction.
Utilizing silyl ketene acetals as nucleophiles.
Employing benzopyrylium triflates as electrophiles.

Main Results:

Achieved promising levels of enantiocontrol in the addition reaction.
Demonstrated a rare example of enantioselective, intermolecular chromenone functionalization.
Successfully employed carbonyl-containing nucleophiles.

Conclusions:

The silanediol-catalyzed reaction provides an effective route for enantioselective chromenone functionalization.
This methodology holds significant potential for the synthesis of bioactive chromanones and tetrahydroxanthones.
Represents a valuable advancement in asymmetric catalysis and heterocyclic chemistry.