NUCLEOPHILIC DISPLACEMENT OF N-BENZYL GROUPS: EFFECT OF PYRIDINIUM ON RATES AND MECHANISM

Article abstract of DOI:10.1016/S0040-4039(00)78584-4

Steric acceleration by α-substituents in pyridine leaving groups is quantitatively assessed.Constraint of α-phenyls to near planarity forms superior leaving groups for S_N2 displacements. α-t-Butyl groups significantly increase S_N1 dissociation.