Self-Terminating, Oxidative Radical Cyclizations: A Novel Reaction of Acyloxyl Radicals
- 8 December 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (1) , 14-15
- https://doi.org/10.1021/ja017006o
Abstract
Acyloxyl radicals RC(O)O• (with R = alkyl, aryl) could be trapped through addition to cyclic and open-chain alkynes, where they were found to act as a donor of oxygen atoms. Mechanistically, this radical oxygenation proceeded through a transannular or intramolecular, respectively, radical cyclization cascade, which was finally terminated by release of an acyl radical RC•(O). The reaction led to stereoselective formation of cyclized products, which contained a carbonyl group at the former site of the alkyne triple bond.Keywords
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