Electron-Transfer Reactions of Bicyclo[4.2.1]nonatrienes: Formation of a Bishomoheptafulvene Radical Cation

Christopher J. Abelt, Heinz D. Roth

Research output: Contribution to journalArticle

13 Scopus citations

Abstract

The radical cation (3·+) of 9-methylenebicyclo[4.2.1]nona-2,4,7-triene undergoes rapid intramolecular cyclization to generate an isomeric radical cation (15·+) derived from a tetracyclic structure. In contrast, the hydrocarbon 15 suffers retrocyclization to regenerate 3. The comparative stability of 15·+ is ascribed to its bishomoaromatic character. Four radical cations of less unsaturated model compounds support the assigned structure.

Original languageEnglish (US)
Pages (from-to)6734-6739
Number of pages6
JournalJournal of the American Chemical Society
Volume108
Issue number21
DOIs
StatePublished - Jan 1 1986
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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