Electron-Transfer-Induced Reorganization of Bicyclo[6.1.0]nonatriene and Derivatives

Heinz D. Roth, Marcia L. Schilling, Christopher J. Abelt, Tsutomu Miyashi, Yasutake Takahashi, Akinori Konno, Toshio Mukai

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10 Scopus citations


The radical cations of bicyclo[6.1.01nonatriene (1a) and several derivatives (1b-f) have been generated by photoinduced electron transfer in solution. The radical cation 3a, derived from the parent, has a weakened cyclopropane bond with spin (and charge) density at C1 and C8. Electron return in singlet pairs regenerates la, whereas triplet recombination gives rise to cyclononatetraene (6). Electron-withdrawing substituents at C9(Cl, 1c) cause spin and charge to be restricted to the triene moiety. The 9,9-diphenyl derivative 1d undergoes electron-transfer-induced rearrangement to 7-(β,β-diphenylethenyl)-cycloheptatriene, whereas the spirofluorene derivative 1f is converted to a barbaralane derivative 9f. The homoaromatic radical cation 10f is suggested as an intermediate in this remarkable rearrangement.

Original languageEnglish (US)
Pages (from-to)5130-5136
Number of pages7
JournalJournal of the American Chemical Society
Issue number15
StatePublished - Jul 1988
Externally publishedYes

All Science Journal Classification (ASJC) codes

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


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