Protonation of tetrafluoro‐2,11‐dithia [3·3]paracyclophane and tetrafluoro‐2,11‐dithia [3·3]metaparacyclophane in high‐acidity super acid media, namely FSO3H.SbF5 (1:1) ‘magic acid’–SO2CIF, gave their corresponding acidic disulfonium ions. Additional ring protonation to give a disulfonium–monoarenium trication was not observed. With the non‐fluorinated 2,11‐dithia [3·3] cyclophanes, the disulfonium ions can be ring protonated in equilibrium to give a dynamic disulfonium–monoarenium trication. Tetrafluoro [2·2]‐metaparacyclophane is monoprotonated at the meta ring and gives a complex mixture of conformational isomers. Multinuclear magnetic resonance data on the cyclophane precursors and their derived cations are compared and analysed. The energies, conformations and charge distributions of the isometric fluorinated and non‐fluorinated [2·2] ‐ and dithia [3·3] cyclophanes were calculated by the AM1 and PM3 methods, respectively. In all but one case the cyclophane arenium ions predicted by theory to be energetically most favoured are those observed in solution under stable ion conditions. In agreement with experiment, the instabilities of S,S,C‐cyclophane trications are also theoretically predicted.

In this paper, we describe the technique of analytical highspeed countercurrent chromatography coupled with electrospray ionization mass spectrometry (HSCCCESIMS) for the first time, and evaluate its performance in terms of chromatography and mass spectrometry. This technique demonstrates the capability and resolving power of HSCCC in the separation of a few natural product mixtures and utilizes ESIMS as a detector with continuous detection and high sensitivity. Application of this HSCCC/ESIMS system is illustrated by the separation and detection of biologically important compounds. 65

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