The mechanism of deamination of methoxy substituted tritylammonium ions in methanolic aqueous acid

Abstract

In methanolic aqueous acid, methoxy-substituted tritylammonium ions undergo heterolysis to give an equilibrium mixture of the substituted trityl cation, the corresponding alcohol (and methyl ether), and the ammonium cation via an S_N1 mechanism; the detection of a reaction channel first order in hydronium ions may implicate substituted trityl cation–ammonia (ion–molecule) pairs as reactive intermediates.