Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

5.2K
The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
5.2K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

12.2K
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.
12.2K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

7.0K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
7.0K
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

4.4K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
4.4K
Halogenation of Alkenes02:46

Halogenation of Alkenes

21.7K
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.
21.7K
Preparation of Epoxides03:00

Preparation of Epoxides

10.2K
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...
10.2K

You might also read

Related Articles

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

Sort by
Same author

Colorimetric correction of electrocatalytic urea quantification.

Nature communications·2026
Same author

Discovery of a Robust Single-Atom Ruthenium Emission Control Catalyst.

Angewandte Chemie (International ed. in English)·2026
Same author

Cobalt Nanoparticles Confined in Defective Carbon Matrices for Robust Intermittent CO<sub>2</sub> Methanation.

Angewandte Chemie (International ed. in English)·2026
Same author

Single Atom Ru Doped CuTi Nanozyme with Precisely Programmed Cascade Catalysis for Amplified Oral Cancer Therapy.

ACS nano·2026
Same author

Advanced Single-Atom Catalysts for Thermal-Catalytic C1 Chemistry.

Chemical reviews·2026
Same author

Investigating the Correlation Between Choroidal Alteration and Visual Function Metrics in Dysthyroid Optic Neuropathy.

Translational vision science & technology·2026

Related Experiment Video

Updated: Apr 21, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

8.4K

Sunlight-Driven Olefin Epoxidation via a Bromide Radical-Mediated Process.

Limin Liu1, Mengke Zhang1, Zixiang Huang1,2

  • 1National Synchrotron Radiation Laboratory (NSRL), University of Science and Technology of China, Hefei, Anhui 230029, P. R. China.

Journal of the American Chemical Society
|April 19, 2026
PubMed
Summary

This study introduces a novel, eco-friendly method for producing epoxides using sunlight and a bromine-mediated pathway. This photodriven approach offers a sustainable alternative to traditional methods, reducing energy consumption and CO2 emissions in chemical manufacturing.

More Related Videos

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

12.5K
Light-driven Enzymatic Decarboxylation
09:58

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

12.5K

Related Experiment Videos

Last Updated: Apr 21, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

8.4K
Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

12.5K
Light-driven Enzymatic Decarboxylation
09:58

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

12.5K

Area of Science:

  • Catalysis
  • Photochemistry
  • Green Chemistry

Background:

  • Epoxides are vital industrial chemicals, but current production methods (olefin oxidation with O2) are energy-intensive and generate significant CO2.
  • Developing sustainable and efficient epoxide synthesis routes is crucial for the chemical industry.

Purpose of the Study:

  • To develop a novel, photodriven, bromine-mediated pathway for olefin epoxidation.
  • To achieve high yields and selectivity for ethylene oxide production using a sustainable method.

Main Methods:

  • Utilized a Pd3.91Au0.50/TiO2 catalyst under simulated and natural sunlight.
  • Investigated a bromine-mediated pathway involving photogenerated radicals and intermediate cyclization.
  • Tested the method's applicability across various olefin substrates.

Main Results:

  • Achieved a high ethylene oxide yield rate of 7.19 mmol g-1 h-1 with 90.3% selectivity under simulated sunlight.
  • Produced 862.9 mg of ethylene oxide over 40 hours using natural sunlight.
  • Demonstrated broad substrate scope, including linear, cyclic, and aromatic olefins.

Conclusions:

  • The photodriven Br-mediated pathway is a highly effective and sustainable strategy for olefin epoxidation.
  • Alloying Au and Pd on TiO2 optimizes the catalytic process by modulating adsorption and promoting intermediate formation.
  • This method presents a promising green alternative for industrial epoxide production.