96845-82-8Relevant academic research and scientific papers
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.
Synthesis of 2-indanones via [4 + 1] annulation reactions of (trialkylsilyl)arylketenes
Dalton, Audra M.,Zhang, Yongjun,Davie, Christopher P.,Danheiser, Rick L.
, p. 2465 - 2468 (2007/10/03)
(Matrix presented) (Trialkylsilyl)arylketenes combine with (trimethylsilyl)diazomethane in a new [4 + 1] annulation process leading to 2-indanone derivatives. The (trialkylsilyl)arylketene annulation substrates are available via the photochemical Wolff rearrangement of α-silyl-α-diazo ketones, which are themselves prepared by silylation of the corresponding diazo ketones. The mechanism of the annulation reaction is proposed to involve the formation of a 2,3-bis(silyl)cyclopropanone, which is in equilibrium with an oxyallylic cation. Electrocyclic closure of this intermediate forms the new cyclopentenone ring.
Preparation of 1-Aryl-2-siloxyalkynes from Silylated α-Diazo Carbonyl Compounds
Maas, Gerhard,Brueckmann, Ralf
, p. 2801 - 2802 (2007/10/02)
Silylated α-diazo carbonyl compounds R3SiC(N2)C(O)Ar, prepared from a monosubstituted α-diazo carbonyl compound with trialkylsilyl triflates, rearrange to 1-aryl-2-siloxyalkynes with loss of N2 at or above room temperature, this novel transformation is th
