751453-62-0Relevant academic research and scientific papers
Preparation of N-Silyl-enamines from α-Silyl Carbanions and Aromatic Nitriles
Konakahara, Takeo,Kurosaki, Yoshihiro
, p. 1068 - 1086 (2007/10/02)
The preparations of seven N-silyl-enamines (1a) - (1g) and their chemical behaviour are reported.Lithiated 4-(trimethylsilylmethyl)pyridine (2b) easily reacted with benzonitrile (4a) in tetrahydrofuran to give only (E)-1-phenyl-2-(4-pyridyl)-1-(trimethylsilylamino)ethene (1b) in 90percent yield.On the other hand, lithiated t-butyl trimethylsilylacetate (2c) did not react with (4a) at all, but reacted readily with 2- or 4-cyanopyridines, (4b) or (4c), and scarcely at all reacted with 3-cyanopyridine (4d) to give the corresponding t-butyl (Z)-3-trimethylsilylamino-3-pyridylpropenoates (1c), (1d), and (1e) in 68, 75, and 4percent yields, respectively.The reaction of 3-methyl-5-(trimethylsilylmethyl)isoxazole (2d) with the nitriles (4a) or (4b) gave the corresponding N-silyl-enamine (1g) or the desilylated enamines (5b,c), which were unstable and were readily hydrolyzed to the corresponding ketones (6a) or (6b).
