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N,N,N′,N′ -Tetramethylurea diethylacetal reacts with CH 2 -acidic compounds as benzylcyanide, cyanoacetic acid derivatives malonodinitrile and nitromethane to give ketene aminals or ketene-O,N-acetales. Low polar solvents favour mostly the formation of ketenaminals. The yields of ketenaminals and ketene-O,N-acetals can be improved in some cases by addition of trimethylsilyldimethylamine. The reactions of the urea acetal with diethylmalonate, ore acetyl acetone, stops at the stage of the  N , N ′, N″ -permethylated guanidinium salts with carbanionic counterions. The formation of bis(dimethylamino)methylene-diethylmalonate from the urea acetal and diethylmalonate can be initiated by addition of trimethylsilyldimethylamine/trimethylsilylcyanide.  N,N,N′,N′,N″,N″- Hexamethylguanidinium cyanide is formed in the analogous reactions of the urea acetal with  N,N- dimethylcyanacetamide or diethylsuccinate. The  N,N′,N″ -Hexamethyl-guanidinium nitrite can be obtained from the urea acetal and nitropropane.

Orthoamide und Iminiumsalze, CI. Umsetzungen von N,N,N′,N′- Tetramethylharnstoffdiethylacetal mit CH 2 -aciden Verbindungen