Reactions of N-(Arylsulfonoxy)-N-benzylmethylamines with Sodium Methoxide in Methanol

Article abstract of DOI:10.1021/ja00260a015

Reactions of N-(arylsulfonoxy)-N-benzylmethylamines (1) with MeONa in MeOH have been investigated.The eliminations are quantitative, producing only benzylidenemethylamines.The reactions are first order in substrate and first order in base, and an E2 mechanism is evident.Comparison of the rate data reveals that the arenesulfonates are better leaving groups than halogens in imine-forming elimination.For elimination from 1, ρ = 1.14, k_H?k_D = 3.6, ρ_lg = 1.30, and β_1g = -0.43 have been calculated.Differences in the transition-sate characters for imine-forming eliminations from ArCH2N(Cl)CH3 and 1 have been intepreted in terms of changes in the leaving-group properties and base strength.