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- Title
Exploring Diradical Chemistry: A Carbon-Centered Radical May Act as either an Anion or Electrophile through an Orbital Isomer.
- Authors
Gonçalves, Théo P.; Mohamed, Mubina; Whitby, Richard J.; Sneddon, Helen F.; Harrowven, David C.
- Abstract
Diradical intermediates, formed by thermolysis of alkynylcyclobutenones, can display radical, anion, or electrophilic character because of the existence of an orbital isomer with zwitterionic and cyclohexatrienone character. Our realization that water, alcohols, and certain substituents can induce the switch provides new opportunities in synthesis. For example, it can be used to shut down radical pathways and to give access to aryl carbonates and tetrasubstituted quinones.
- Subjects
CARBON; RADICALS (Chemistry); ELECTROPHILES; ISOMERS; THERMOLYSIS; SUBSTITUENTS (Chemistry)
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 15, p4614
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201411334