Abstract
Monothia[3.2]- and dithia[3.3]metacyclophanes 1–5 are S-protonated in FSO3H·SbF5 (4 ∶ 1)–SO2 (or SO2ClF) superacids to give their corresponding acidic mono- and bis(sulfonium) cations. A detailed NMR study of the resulting cations and their precursors is provided; conformational aspects are also addressed via NOE measurements. PM3 calculations are used in selected cases as a guiding tool to identify preferred conformations. A remarkable deactivation of the aryl rings occurs upon S-protonation, whereby further ring protonation to form disulfoniomonoarenium trications does not occur, even though positive charge delocalization into the phenyl rings is limited.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
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