Kinetics and mechanisms of nucleophilic displacements with heterocycles as leaving groups. Part 4. 2,4,6-Triaryl-N-benzylpyridinium cations: rate variation with electronic effects in the leaving group

Abstract

Electron-withdrawing groups in the 4-phenyl ring of 2,4,6-triphenylpyridine modestly increase its activity as a leaving group. Replacement of 2-phenyl by heteroaryl has a small effect for monoheteroaryl groups, but significantly larger for 2-benzimidazol-2-yl and especially for 2-benzothiazol-1 -yl.