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 eliminations. for eliminations from 1, ρ = 1.14, kH/kD= 3.6, ρlg= 1.30, and βlg= -0.43 have been calculated. Differences in the transition-state characters for imine-forming eliminations from ArCH2N(Cl)CH3and 1 have been interpreted in terms of changes in the leaving-group propensities and base strength.
ASJC Scopus subject areas
- Colloid and Surface Chemistry