Abstract
The formation of 3-aminocrotononitrile and 4-amino-2,6-dimethylaminopyrimidine has been observed during the course of the hydrogermolysis reaction between a germanium amide and a germanium hydride, either as the free amines or bound to germanium as ligands consisting of their conjugate bases. These species arise from the dimerization or trimerization of acetonitrile, and have only been detected when germanium amides having substantial steric bulk at the germanium center are employed in the reaction. The isolation of germanium-bound 3-aminocrotononitrile compounds suggests that α-germyl nitrile species R 3GeCH 2CN that result from the reaction of the germanium amides R 3GeNMe 2 with CH 3CN solvent also can further react with CH 3CN to generate the 3-aminocrotononitrile and 4-amido-2,6-dimethylaminopyrimidine species. The two germanes Ph 3Ge[NHC(CH 3) CHCN] and 2,6-dimethyl-4-(triphenylgermylamino)pyrimidine have been prepared and structurally characterized, and the conversion of Ph 3GeCH 2CN to Ph 3Ge[NHC(CH 3) CHCN] and 2,6-dimethylamino-4-(triphenylgermylamino)pyrimidine as well as the conversion of Ph 3Ge[NHC(CH 3) CHCN] to 2,6-dimethyl-4-(triphenylgermylamino)pyrimidine in acetonitrile solvent has been observed using 1H NMR spectroscopy.
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