Abstract
N,N′,N″-Triaminoguanidinium chloride (TAG-Cl) reacts with cyclopentanone or cyclohexanone to afford 8-(2-cyclopentylidenehydrazinyl)-6,7,9,10-tetraazaspiro[4.5]decan-8-ylium and 3-(2-cyclohexylidenehydrazinyl)-1,2,4,5-tetraazaspiro[5,5]undecan-3-ylium salts, respectively, i. e., two arms of the TAG ion were engaged in spiroaminal formation and the NH2 group of the third arm underwent imine-forming condensation. Ring-opening reactions of the cyclopentanone derived spiroaminal with aldehydes, aryl ketones, aromatic or aliphatic isocyanates give access to a variety of unsymmetrically substituted derivatives of the TAG ion.
Acknowledgments
We thank Bernhard Müller (Institute of Inorganic Chemistry II) for the X-ray diffraction data collection and Dr. Markus Wunderlin for the mass spectra.
Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: None declared.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
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