(8-Dimethylamino-1-naphthyl)trimethylammonium tetrafluoroborate undergoes kinetic N- and equilibrium C-protonation in strong acids; ring deuteriation may involve rate-limiting ring inversion in the non-planar C-protonated dication.
R. W. Alder and N. C. Goode, J. Chem. Soc., Chem. Commun., 1976, 108 DOI: 10.1039/C39760000108
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