• NMR;
  • 19F;
  • 13C;
  • 1H;
  • HOESY;
  • 19F-13C HSQC;
  • cyclophane;
  • paracyclophane

Pseudo-meta and pseudo-para diamino-octafluoro[2.2]paracyclophanes are challenging to separate either by chromatography or recrystallization, but through the use of a mixture of the two isomers, the 1H, 19F, and 13C NMR spectra of these compounds have been fully and unambiguously assigned using 1H COSY, 1H-19F HOESY, 1H-13C HSQC, 1H-13C HMBC, and 19F-13C HSQC techniques. This permits the easy identification of either of the individual isomers. In addition, the 13C spectrum of the pseudo-ortho analogue is reported and assigned for the first time. The gem shift effect in this series of bridge-fluorinated paracyclophanes serves to deshield 1H resonances and shield 13C. Copyright © 2012 John Wiley & Sons, Ltd.