One-pot electrosynthesis of substituted imidazolinium and tetrahydropyrimidinium salts from secondary alkyldiamines: an electrochemical route toward ionic liquids.
A one-pot electrosynthetic procedure has been developed to afford imidazolium and tetrahydropyrimidinium cationic derivatives from secondary alkyl diamines in neutral media. To this end, electrochemical oxidation of a series of aliphatic diamines (1-9) has been investigated. Mechanistic information is provided from analysis of the cyclic voltammetry data and identification of intermediate species and final products. The coexistence of two first-order chemical reactions, C(alpha)-H and C(alpha)-C(beta), at the radical cation level leading to identical final products is suggested to justify not only the nature but also the yields of the salts obtained.
Gallardo
Iluminada
I
Departament de Química, Universitat Autònoma de Barcelona, 08193 Barcelona, Spain. iluminada.gallardo@uab.cat
Vilà
Neus
N