C−F Bond Cleavage by Intramolecular S_N2 Reaction of Alkyl Fluorides with O- and N-Nucleophiles

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 SN2 reaction mechanism.