Unambiguous characterization of aminocyanoimide (the adduct of ammonia addition to cyanogen) has remained elusive due to its reactivity with water and a lack of a clear method for isolation, despite some reports.1 Recently cyanoamidinium chloride, the acid salt, was crystallized from acidic aqueous solution.2 Under acidic conditions, these compounds are stable as solid species. Further reactions with azides have been carried out to enter high nitrogen content heterocycles which exhibit remarkable stability. The scope, properties, and reactivity of cyanoamidinium salts will be reported.1. Ito, M. Jpn. Tokkyo Koho., 1974, JP49020182 B 19740523.2. Uchiyama, Y.; Dolphin, J. S.; Kelley, S.; Arduengo III, A. J., Harlow, R. L.; Marshall W. J. private communication, 2012.

Preparation and reactivity of cyanoamidinium salts

245th National Meeting (2013)

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