Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 4, Pages 1413-1421Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo702261u
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Intermolecular addition of photochemically generated N-centered aminium and amidyl radicals 13a-d and 16a,b, respectively, to the cyclic alkyne 1 initiates a radical translocation/cyclization cascade, followed by an oxidative termination step that eventually leads to formation of the bicyclic ketones 7a and 8a. Computational studies were performed to gain insight into the mechanism of these reactions, which are an interesting modification of the recently discovered concept of self-terminating radical cyclizations.
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