Related Experiment Videos
Anion radical chain cycloaddition of tethered enones: intramolecular cyclobutanation and Diels-Alder cycloaddition
Yeonsuk Roh1, Hye-Young Jang, Vincent Lynch
1Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
Organic Letters
|February 15, 2002
Abstract:
[reaction: see text] 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 Diels-Alder product is observed. Parallel trends in substrate scope vis-à-vis the Co-catalyzed bis(enone) cyclobutanation are discussed.