Imidazol-2-and-4-ylidene by decarboxylation. Studies on the cross-conjugated mesomeric betaine-alkaloid norzooanemonine and its pseudo-cross-conjugated isomer |
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Authors: | Schmidt Andreas Beutler Ariane Albrecht Marcel Snovydovych Bohdan Ramírez Francisco Javier |
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Institution: | Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, D-38678, Clausthal-Zellerfeld, Germany. schmidt@ioc.tu-clausthal.de |
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Abstract: | 1,3-Dimethylimidazolium-2-carboxylate and -4-carboxylate (norzooanemonine), which belong to two distinct classes of heterocyclic mesomeric betaines, undergo thermal decarboxylations to the N-heterocyclic carbenes imidazol-2-ylidene and imidazol-4-ylidene, respectively. These carbenes can be detected by ESI mass spectrometry and can be trapped by isocyanates to imidazolium-amidates, the structure of which was proved by independent syntheses. We performed calculations to characterize the different types of conjugation in the imidazolium-carboxylates. |
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