Abstract
2-Allyl-3-benzylamino-2-cyclohexenones undergo iodine-methanol–promoted iodocyclisation under reflux to afford products characterised by combination of NMR (1H and 13C), IR and mass spectroscopic techniques as the conjugated iodolium betaine derivatives of 2-iodomethyltetrahydroindolones. The zwitterionic nature of the products in solution and in the solid state was also confirmed by their chemical behaviour and the experimental data were corroborated by information from quantum chemical calculations.
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