Trimethylgermylation and trimethylsilylation of N,N-dialkylacetamides and application of their anions to the Peterson-type reaction

Article abstract of DOI:10.1016/0022-328X(88)87041-4

Base-assisted trimethylsilylation and trimethylgermylation of N,N-dimethylacetamide (1a) or 1-acetylpiperidine (1b) were carried out.The germyl group was introduced stepwise onto the methyl carbon of the acetyl group to give mono- (3), bis- (6), or tris(trimethylgermyl)acetamides (9b), respectively, in high yields, whereas under similar conditions the second silyl group was usually introduced at the carbonyl-oxygen.The Peterson-type reaction of N,N-dimethyl(trimethylgermyl)(trimethylsilyl)acetamide (5a) with aldehydes gave preferentially N,N-dimethyl-2-(trimethylgermyl)-2-alkenamides (13).