Related Experiment Video
Updated: Mar 9, 2026

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
Published on: April 22, 2016
Sequential α-Aminoalkyl Radical and Oxygen-Centered Radical Reactions of Vinyl Bromide-Tethered Tricyclic Lactones
Chia-Hung Lin1, Zheng-Feng Zhang1, Shan-Shan Chou1
1Department of Applied Chemistry, National Chiayi University, Chiayi City, Taiwan.
Abstract:
Tricyclic lactone compounds featuring a vinyl bromide tether were investigated for intramolecular radical cyclization. α-Aminoalkyl radicals, generated through the translocation of an initially generated vinyl radical, underwent cyclization or cyclization/1,5-hydrogen transfer, C─O bond fragmentation, and further cyclization to construct the nitrogen-containing heterocyclic rings. When two diastereomers with substituents in opposite stereochemical configurations underwent radical reactions separately, they yielded distinct products. Density functional theory (DFT) calculation studies were carried out to unravel mechanistic insights in this process.
Related Concept Videos
Radical Reactivity: Electrophilic Radicals
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
Radical Substitution: Allylic Chlorination
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
Radical Reactivity: Nucleophilic Radicals
Radical Chain-Growth Polymerization: Mechanism

