Experimental evidence of partially rate limiting ion-pair interconversion in a base catalyzed 1,3-proton transfer reaction
Abstract
The relative rates for interconversion and reprotonation of the ion-pair intermediates are of the same order of magnitude in the piperidine catalyzed ‘degenerate’ rearrangement of 1,3-dimethylindene, as investigated using 1H and 2H NMR spectroscopy by letting the 1,3-hydron transfer reaction compete with isotope (1H/2H) exchange.