1078202-83-1Relevant articles and documents
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.