Undecafluoropiperidine → 2-Fluoropyridine

Recently attention has been directed to the use of compounds of the N-F class, i.e. having an N-F bond, as electrophilic fluorinating agents. The prototypical member of this class is perfluoro-N-fluoropiperidine (R. E. Banks and G. E. Williamson, Chem. Ind. (London), 1964, 1864 and R. E. Banks et al, J. Chem. Soc., Perkin Trans. I, 1972, 1098). However, this compound is obtainable only in low yields by electrochemical fluorination of pyridine (about 8% yield) or 2-fluoropyridine (about 13% yield) in anhydrous hydrogen fluoride. Further, it has been found to be inadequately reactive in several applications and, on transfer of fluorine to a carbanionic substrate, liberates the imidoyl fluoride perfluoro-1-azacyclohex-1-ene which then competes for the substrate. Similar problems militate against use of the analogous compounds perfluoro-(N-fluoro-2,6-dimethylpiperidine) and perfluoro-N-fluoromorpholine (R. E. Banks et al, J. Chem. Soc., Perkin Trans. I, 1988, 2805) and of poly[perfluoro-(N-fluoropiperidin-4-ylethylene)] (R. E. Banks & E. Tsiliopoulos, J. Fluorine Chem., 1986, 34, 281) as electrophilic fluorinating agents.

ORD record

ord-23a7d21d73974639a16730d3ba6aaf58

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05086178