Electrophilic reactivities of α,β-unsaturated iminium ions

Abstract

(Chemical Equation Presented) How fast do nucleophiles add to iminium ions? Kinetic studies of the reactions of seven iminium ions 1 with cyclic ketene acetals 2 rendered electrophilicity parameters E for these iminium ions. Because N and s parameters are known for numerous nucleophiles, the correlation log k(20°C)= s(N+E) makes it possible to calculate rate constants for nucleophilic attack at the iminium ions 1. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.