59050-70-3Relevant academic research and scientific papers
FLUORINATIONS WITH COMPLEX METAL FLUORIDES PART 8. RING REARRANGEMENT IN THE FLUORINATIONS OF QUINOLINE WITH CAESIUM TETRAFLUOROCOBALTATE AND WITH COBALT(III) FLUORIDE
Plevey, Raymond G.,Rendell, Richard W.,Tatlow, John Colin
, p. 413 - 428 (2007/10/02)
Fluorination of quinoline by caesium tetrafluorocobaltate at ca. 350 deg C afforded mainly a mixture of pentadecafluoro-2-azabicyclodec-1(2)-ene (E), and heptadecafluoro-1-azabicyclodecane (F), arising by skeletal rearrangement.Minor products were six polyfluorocyclohexapyridines (G-L) all with carbocyclic rings having the -(CF2)4 - moiety.Compound F was unreactive, but E was highly susceptible to nucleophiles, e.g. water and methanol.Isoquinoline was fluorinated similarly, but the only new product isolated was tridecafluoro-3-azabicyclodeca-1(6)-2-diene (R).The rearrangement occurring with quinoline prompted a re-examination of its fluorination by cobalt(III) fluoride.At ca. 350 deg C, compound F was the major product, with very little E: there were some ring-opened materials, the most important being tetradecafluoro-4-pentafluoroethyl-2-azaoct-2(Z)-ene (N).
