C−F Bond Cleavage by Intramolecular SN2 Reaction of Alkyl Fluorides with O- and N-Nucleophiles
The Journal of Organic Chemistry2009Vol. 74(7), pp. 2850–2853
Citations Over TimeTop 12% of 2009 papers
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.
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