title: C-F bond cleavage by intramolecular S(N)2 reaction of alkyl fluorides with O- and N-nucleophiles.
abstract: The nucleophilic substitution of alkyl fluorides was achieved in the intramolecular reactions with O- and N-nucleophiles. The intramolecular defluorinative cyclization reaction was influenced by the nature of nucleophiles, the size of the ring to be formed, and the comformational rigidity of the precursors. Intermolecular nucleophilic substitution reactions of alkyl fluorides under similar reaction conditions were found to be difficult. The stereochemistry study of the current C-F bond cleavage reaction showed a complete configurational inversion, which supports an intramolecular S(N)2 reaction mechanism.
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: Laijun
authors.initials: L
authors.lastname: Zhang
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.forename: Jun
authors.initials: J
authors.lastname: Liu
authors.forename: Jinbo
authors.initials: J
authors.lastname: Hu