Free-radical hydrogen-atom abstractions from substituted cumenes

1968 ◽  
Vol 33 (1) ◽  
pp. 332-336 ◽  
Author(s):  
Gerald J. Gleicher
Keyword(s):  
Free Radical ◽  
Hydrogen Atom

Recent advances in Minisci-type reactions and applications in organic synthesis

2020 ◽  
Vol 24 ◽  
Author(s):  
Wengui Wang ◽  
Shoufeng Wang
Keyword(s):  
Free Radical ◽  
Hydrogen Atom ◽  
Organic Synthesis ◽  
Radical Reactivity ◽  
Atom Loss ◽  
Radical Generation ◽  
In Situ Generation ◽  
Thermal Cleavage ◽  
Synthetic Chemist

Abstract:: Minisci-type reactions have become widely known as reactions that involve the addition of carbon-centered radicals to basic heteroarenes followed by formal hydrogen atom loss. While the originally developed protocols for radical generation remain in active use today, in recent years by a new array of radical generation strategies allow use of a wider variety of radical precursors that often operate under milder and more benign conditions. New transformations based on free radical reactivity are now available to a synthetic chemist looking to utilize a Minisci-type reaction. Radical-generation methods based on photoredox catalysis and electrochemistry, which utilize thermal cleavage or the in situ generation of reactive radical precursors, have become popular approaches. Our review will cover the remarkably literature that has appeared on this topic in recent 5 years, from 2015-01 to 2020-01, in an attempt to provide guidance to the synthetic chemist, on both the challenges that have been overcome and applications in organic synthesis.

Thiols as an Efficient Hydrogen Atom Donor in Free Radical Transformations in Aqueous Media

2010 ◽  
Vol 14 (10) ◽  
pp. 1075-1082 ◽  
Author(s):  
Ioannis N. Lykakis ◽  
V. Tamara Perchyonok
Keyword(s):  
Free Radical ◽  
Hydrogen Atom ◽  
Aqueous Media

Markovnikov free radical addition reactions, a sleeping beauty kissed to life

2016 ◽  
Vol 45 (3) ◽  
pp. 577-583 ◽  
Author(s):  
Reinhard W. Hoffmann
Keyword(s):  
Free Radical ◽  
Double Bond ◽  
Hydrogen Atom ◽  
Sleeping Beauty ◽  
Radical Addition ◽  
Addition Reactions ◽  
Free Radical Addition

This review covers free radical additions, which are initiated by the formal addition of a hydrogen atom to a CC double bond.

scholarly journals COMPARATIVE ANTIRADICAL ACTIVITY AND MOLECULAR DOCKING STUDY OF BERGAPTOL AND XANTHOTOXOL

2020 ◽  
pp. 71-84
Author(s):  
Žiko Milanović ◽  
Marko Antonijević ◽  
Jelena Đorović ◽  
Dejan Milenković
Keyword(s):  
Antioxidant Activity ◽  
Electron Transfer ◽  
Molecular Docking ◽  
Free Radical ◽  
Hydrogen Atom ◽  
Antiradical Activity ◽  
Docking Study ◽  
Hydrogen Atom Transfer ◽  
Molecular Docking Study ◽  
Anionic Species

The antioxidant activity of bergaptol (4-hydroxyfuro[3,2-g]chromen-7-one, BER) and xanthotoxol (9-hydroxyfuro[3,2-g]chromen-7-one, XAN) was investigated in water and benzene, as solvents. For this purpose, the density functional theory (DFT) was used. The free radical scavenging potency of investigated compounds towards different reactive oxygen species (ROS) was performed. Antioxidative mechanism of investigated compounds – hydrogen atom transfer (HAT), single-electron transfer–proton transfer (SET-PT) and sequential proton loss electron transfer (SPLET) were examined using M06-2X/6-311++G(d,p) theoretical model. The important thermodynamic parameters (BDE, IP, PDE, PA, ETE) and Gibbs free energies of reactions, were used to determine the most probable antioxidant mechanism of action. The obtained thermodynamic parameters suggested that Hydrogen Atom Transfer (HAT) is the most probable reaction pathway in benzene, while Sequential Proton Loss Electron Transfer (SPLET) was favorized in water. The obtained results indicate that the favorable mechanism of antiradical activity depends on the polarity of medium and the nature of free radical species. By comparing the antioxidant activity of investigated compounds, it can be concluded that bergaptol exhibits better antioxidant properties. Molecular docking study of neutral and anionic species of investigated compounds was performed according to Estrogen receptor alpha (ERα). In both cases, bergaptol showed better inhibitory potency. All the anionic species showed a higher inhibition constant, indicating lower inhibition potency than corresponding parent molecules.

Sign in / Sign up

Export Citation Format

Share Document