1078202-84-2Relevant academic research and scientific papers
Facile synthesis of multifunctionalized allenes by magnesium-promoted reductive silylation of aromatic conjugated ynones
Maekawa, Hirofumi,Takano, Atsushi,Watanabe, Masamitsu
supporting information, p. 6208 - 6211 (2014/12/10)
Mg-promoted reductive silylation of 4-phenyl-3-butyn-2-one in N,N-dimethylformamide (DMF) in the presence of chlorotrimethylsilane brought about double silylation at the β-carbon and oxygen atoms of the carbonyl group to give a multifunctionalized allene with a vinylsilane moiety and a silyl enol ether moiety. A variety of allenes can be synthesized through this simple methodology. Acid-catalyzed hydrolysis of an allene derived from the trimethylsilylation of 4-phenyl-3-butyn-2-one resulted in the formation of the corresponding benzalacetone with a trimethylsilyl group at the β-position of the carbonyl group in high yield.
Aryl trialkylsilyl ketenes: Acid-catalyzed synthesis from 1-aryl-2-diazo-2-trialkylsilylethanones and their conversion into 3-silyl-1-silyloxyallenes
Bucher, Stefan M.,Brueckmann, Ralf,Maas, Gerhard
experimental part, p. 4426 - 4433 (2009/05/07)
Aryl-substituted α-silyl α-diazo ketones are readily transformed into aryl silyl ketenes in the presence of a catalytic amount of triflic acid. Thus, a convenient method to prepare these silyl ketenes becomes available, which combines two steps, silylation of an aryl diazomethyl ketone and acid-induced Wolff rearrangement of the formed α-silyl α-diazo ketone, in a one-pot procedure. It appears that the trialkyl-ammonium salt, which is formed in the silylation step, can also catalyze the Wolff rearrangement, but distinctly more slowly than the proton acid. The silyl ketenes react smoothly with α-silyl α-diazo ketones to form 3-silyl-1-silyloxyallenes in fairly good yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
