Journal
ORGANIC LETTERS
Volume 4, Issue 4, Pages 611-613Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0172065
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[GRAPHICS] The anion radicals of certain bis(enones), generated by cathodic reduction, are observed to participate in intramolecular cyclobutanation, yielding bicyclo[3.2.0]heptane derivatives through an anion radical chain mechanism. Evidence for stepwise cycloaddition involving distonic anion radical intermediates is presented. In addition to the novel anion radical cyclobutanations, an unprecedented intramolecular anion radical Diets-Alder product is observed. Parallel trends in substrate scope vis-a-vis the Co-catalyzed bis(enone) cyclobutanation are discussed.
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