Base-Induced Imine-Forming 1,2-Elimination Reactions in the Gas Phase

The gas-phase reactivity of CH 3 NHOCH 3 (N,O-dimethylhydrorylamine, DHA) and NH 2 OCH 3 (O-methylhydrorylamine, MHA) toward a series of anionic bases has been studied using the method of Fourier transform ion cyclotron resonance (FT-ICR) miass spectrometry. Both DHA and MHA undergo a competing proton attraction from and nucleophilic substitution reaction on the nitrogen atom. The competition between these processes is governed by the strength of the base used. Unexpectedly, the nucleophilic attack on the nitrogen atom leading to the substitution of the methoxy group is found to be a relatively facile process