[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.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol0172065 | DOI Listing |
Publication Analysis
Top Keywords
anion radical
20
radical chain
8
intramolecular cyclobutanation
8
anion
6
chain cycloaddition
4
cycloaddition tethered
4
tethered enones
4
enones intramolecular
4
cyclobutanation diels-alder
4
diels-alder cycloaddition
4
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!