When Anthracene and Quinone Avoid Cycloaddition: Acid-Catalyzed Redox Neutral Functionalization of Anthracene to Aryl
1School of Physical Science and Technology, ShanghaiTech University, 393 Middle Huaxia Road, Shanghai 201210, China.
Abstract:
Benzoquinone and 9-phenylanthracene barely undergo anticipated cycloaddition under acid catalysis. Instead, 9-anthracenyl aryl ethers are obtained as unexpected products. Mechanistic studies indicate that the reaction likely undergoes an ionic mechanism between protonated anthracene species and nucleophilic oxygen of 1,4-benzoquinone or 1,4-hydroquinone. A variety of 9-anthracenyl aryl ethers are constructed with this method. Produced anthracenyl aryl ethers are potential scaffolds for new fluorescent molecules.
More Related Videos
Related Concept Videos
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
Nucleophilic Aromatic Substitution: Elimination–Addition
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Oxidation of Phenols to Quinones
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
Cycloaddition Reactions: Overview


![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)