Abstract: Reactions of N-(arylsu1fonoxy)-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. ...
[Smith, Richard F.; Soelch, Richard R.; Feltz, Timothy P.; Martinelli, Michael J.; Geer, Susan M. Journal of Heterocyclic Chemistry, 1981 , vol. 18, p. 319 - 325]
