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

Laijun Zhang, Wei Zhang, Jun Liu and Jinbo Hu*

*Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032, China, Email: jinbohumail.sioc.ac.cn

L. Zhang, W. Zhang, J. Liu, J. Hu, J. Org. Chem., 2009, 74, 2850-2853.

DOI: 10.1021/jo802819p

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Abstract

A nucleophilic substitution of alkyl fluorides was achieved in intramolecular reactions with O- and N-nucleophiles. The reaction is influenced by the nature of nucleophiles, the size of the ring to be formed, and the comformational rigidity of the precursors.

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Key Words

Cyclic Ethers, 1,3-dihydro-2-benzofurans, benzo-fused O-Heterocycles, Isochromans

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ID: J42-Y2009-1000