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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 NH 2  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.

zeitschrift für naturforschung b

Derivatives of the triaminoguanidinium ion, 7: unsymmetrically substituted  N,N  '  ,N  '' -triaminoguanidinium salts  via  a cyclopentanone spiroaminal intermediate