Deuteriodeprotonation of some heteroaromatic bicyclic compounds
Abstract
Rate constants for deuteriodeprotonation in D2SO4 at the 2- and 3-positions of the four isomeric thieno[2,3-b]-, thieno[2,3-c]-, thieno[3,2-b]-, and thieno[3,2-c]-pyridines and of furo[3,2-b]- and seleno[3,2-b]-pyridine have been determined. The slopes of the rate profiles give evidence that all the substrates undergo exchange as protonated species. The relative reactivities are given as standard rates and discussed in terms of electronic effects in heteroaromatic systems.