title: Divergent rearrangements of cyclopropyl-substituted fluoroepoxides involving C-F bond cleavage and formation.
abstract: Unprecedented divergent rearrangements of cyclopropyl-substituted fluoroepoxides are reported. In the presence of a catalytic amount of benzoic acid, cyclopropyl-substituted fluoroepoxides efficiently undergo 1,5-fluorine migration. However, when the fluoroepoxides are heated with K2CO3 at 60 °C, 1,2-fluorine migration occurs. The 1,5-fluorine migration is believed to proceed via a carbocation intermediate, while the 1,2-fluorine migration may involve a tight ion pair intermediate or proceed via a concerted process.
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Ling-Ling Road, Shanghai 200032, China.
authors.forename: Tao
authors.initials: T
authors.lastname: Luo
authors.forename: Rui
authors.initials: R
authors.lastname: Zhang
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.forename: Xiao
authors.initials: X
authors.lastname: Shen
authors.forename: Teruo
authors.initials: T
authors.lastname: Umemoto
authors.forename: Jinbo
authors.initials: J
authors.lastname: Hu