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Updated: Jan 30, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
Radical-induced ring-opening and reconstruction of cyclobutanone oxime esters
Panpan Wang1, Binlin Zhao, Yu Yuan
1College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China. yyuan@yzu.edu.cn.
Abstract:
The first example of intramolecular ring-opening and reconstruction of cyclobutanone oxime esters via selective C-C bond cleavage leading to the synthesis of 3,4-dihydronaphthalene-2-carbonitriles in the presence of a cheap copper catalyst has been reported. The protocol is distinguished by mild and safe reaction conditions that exclude ligands, oxidants, bases, toxic cyanide salts and tolerates a wide scope of cyclobutanones without compromising their efficiency and scalability. The alternative visible-light-driven photoredox process for this coupling reaction was also uncovered.
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