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

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

[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.

Regioselectivity of Electrophilic Additions-Peroxide Effect

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

You might also read

Related Articles

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

Sort by

Same author

Programmable Functionalizations of Tetramethylpiperidine N-Oxyl (TEMPO)-Acrolein Linchpins Derived from Alkoxyallenes.

Journal of the American Chemical Society·2026

Same author

<i>Operando</i> NMR Monitoring of Electrochemical Reactions.

Organic process research & development·2026

Same author

Chiral S(VI) platform unifies selective C-H amination of complex molecules and alkane feedstocks.

Science (New York, N.Y.)·2026

Same author

Silver-catalysed intermolecular benzylic-selective C-H amidation <i>via</i> nitrene transfer.

Chemical science·2026

Same author

Targeting Mycolic Acid Biosynthesis with Cyclic Sulfamates: A New Strategy against <i>Mycobacterium tuberculosis</i>.

ACS infectious diseases·2025

Same author

Two-carbon ring expansion of bicyclic aziridines to oxazocines <i>via</i> aryne insertion into a σ C-N bond.

Chemical science·2025

Search research articles

Related Experiment Video

Updated: Dec 20, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Regioselective Intramolecular Allene Amidation Enabled by an EDA Complex*.

Lu Liu¹, Robert M Ward¹, Jennifer M Schomaker¹

¹Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI, 53706, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|May 26, 2020

Summary

This study details a new method for synthesizing N-heterocycles by adding amidyl radicals to allenes. This regioselective reaction expands the utility of radical chemistry in organic synthesis.

Keywords:

EDA complexes amidyl radicals lactams radical additions to allenes vinyl radicals

More Related Videos

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

Harnessing the Bioorthogonal Inverse Electron Demand Diels-Alder Cycloaddition for Pretargeted PET Imaging

Harnessing the Bioorthogonal Inverse Electron Demand Diels-Alder Cycloaddition for Pretargeted PET Imaging

Published on: February 3, 2015

Related Experiment Videos

Last Updated: Dec 20, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

Harnessing the Bioorthogonal Inverse Electron Demand Diels-Alder Cycloaddition for Pretargeted PET Imaging

Harnessing the Bioorthogonal Inverse Electron Demand Diels-Alder Cycloaddition for Pretargeted PET Imaging

Published on: February 3, 2015

Area of Science:

Organic Chemistry
Radical Chemistry
Synthetic Methodology

Background:

Radical additions to unsaturated precursors are vital for creating organic building blocks.
Mild methods for generating N-centered radicals have increased interest in their synthetic applications.
While additions to alkenes and alkynes are known, additions to allenes are less explored.

Purpose of the Study:

To explore the addition of amidyl radicals to allenes.
To develop a regioselective method for synthesizing N-heterocycles.
To leverage the unique reactivity of allenes in radical transformations.

Main Methods:

Generation of N-centered amidyl radicals under mild conditions.
Regioselective addition of these radicals to various allene substrates.
Characterization of the resulting N-heterocyclic products.

Main Results:

Successful regioselective addition of amidyl radicals to allenes was achieved.
A range of valuable N-heterocycle scaffolds were synthesized.
The reaction demonstrates potential for chirality transfer and diversification of functionality.

Conclusions:

This work establishes a novel and regioselective route for amidyl radical addition to allenes.
The developed methodology provides access to diverse N-heterocyclic scaffolds.
This expands the scope of radical chemistry for constructing complex organic molecules.