100064-25-3Relevant articles and documents
Electron-Transfer-Induced Reorganization of Bicyclononatriene and Derivatives
Roth, Heinz D.,Schilling, Marcia L.,Abelt, Christopher J.,Miyashi, Tsutomu,Takahashi, Yasutake,et al.
, p. 5130 - 5136 (1988)
The radical cations of bicyclononatriene (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 1a, 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.