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.