title: A fluorine 1,2-migration via aryl cation/radical/radical anion/radical sequence.
abstract: Irradiation of a 7-piperazino-8-fluoroquinolone causes formal 1,2-fluorine migration, piperazine loss and reduction, or nucleophile addition in 8. Product study, laser flash photolysis, and computational modeling support F(-) detachment to yield a triplet 8-quinolyl cation that either inserts intramolecularly or is trapped by Cl(-), Br(-). However, iodide and pyrrole reduce it to the radical that continues the 'redox tour' (aryl cation→ radical→ radical anion→ radical and then again radical or radical anion) leading to the rearranged products.
authors.affiliation: Department of Chemistry, University of Pavia, via Taramelli 12, 27100 Pavia, Italy.
authors.forename: Luca
authors.initials: L
authors.lastname: Pretali
authors.forename: Daniele
authors.initials: D
authors.lastname: Dondi
authors.forename: Mila
authors.initials: M
authors.lastname: D'Angelantonio
authors.forename: Ilse
authors.initials: I
authors.lastname: Manet
authors.forename: Elisa
authors.initials: E
authors.lastname: Fasani
authors.forename: Sandra
authors.initials: S
authors.lastname: Monti
authors.forename: Bruna
authors.initials: B
authors.lastname: Bovio
authors.forename: Angelo
authors.initials: A
authors.lastname: Albini