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Paper | Regular issue | Vol 43, No. 3, 1996, pp.567-580
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7294
Synthesis of Dipolar Ethyleneimidazolium Benzimidazolate Inner Salts and Their Transformation to 2-Vinylbenzimidazoles through a Type of β-Elimination Reaction

Ermitas Alcalde,* Maria Gisbert, and Lluïsa Pérez-Garcia

*Laboratorio de Chímica Oránica, Facultad de Fharmacia, Universidad de Barcelona, E-08028 Barcelona, Spain


The synthesis and spectroscopic properties of the fairly stable title inner salts (5) are reported. For several of the betaines (5), both the highly dipolar character due to the terminal rings and the nature of the spacer promoted a type of β-elimination reaction. Thus, formation of 2-vinylbenzimidazoles (7) from the corresponding betaines (5) proceeds in high yield under neutral and mild conditions. Following similar treatment, the 1-(2-benzimidazol-2-ylethyl)imidazolium salt (8b) undergo nucleophilic substitution reactions.