42414-77-7Relevant academic research and scientific papers
Lewis Acid-Activated Reactions of Silyl Ketenes for the Preparation of α-Silyl Carbonyl Compounds
Mitchell, Sarah M.,Xiang, Yuanhui,Matthews, Rachael,Amburgey, Alexis M.,Pentzer, Emily B.
, (2019/11/14)
Silyl-substituted ketenes are attractive molecular building blocks due to their stability and ease of storage, as opposed to unstable alkyl and aryl ketenes. To better understand the reactivity of silyl ketenes and, in turn, their use in the preparation o
Lewis Acid-Activated Reactions of Silyl Ketenes for the Preparation of α-Silyl Carbonyl Compounds
Mitchell, Sarah M.,Xiang, Yuanhui,Matthews, Rachael,Amburgey, Alexis M.,Pentzer, Emily B.
, p. 14461 - 14468 (2019/12/02)
Silyl-substituted ketenes are attractive molecular building blocks due to their stability and ease of storage, as opposed to unstable alkyl and aryl ketenes. To better understand the reactivity of silyl ketenes and, in turn, their use in the preparation o
C2-Symmetric Cu(II) Complexes as Chiral Lewis Acids. Catalytic, Enantioselective Cycloadditions of Silyl Ketenes
Evans, David A.,Janey, Jacob M.
, p. 2125 - 2128 (2007/10/03)
(matrix presented) C2-Symmetric bis(oxazoline)-Cu(II) complexes (4a-g) catalyze the enantioselective [2 + 2] cycloaddition between (silyl)ketenes and chelating carbonyl substrates. A range of substituted β-lactones can be produced in excellent yields and selectivities. It was also found that (trimethylsilyl)-ketene (1) may also undergo a highly selective hetero Diels-Alder reaction with β,γ-unsaturated α-keto esters.
Phenyldimethylsilyl-substituted ketenes and bisketenes
Liu, Ronghau,Marra, Romeo M.,Tidwell, Thomas T.
, p. 6227 - 6232 (2007/10/03)
The phenyldimethylsilyl-substituted monoketene PhMe2SiCH=C=O (1) and bisketene (PhMe2-SiC=C=O)2 (3) have been prepared and compared to the corresponding Me3Si- and t-BuMe2Si-substituted species. The 13C, 17O, and 29Si NMR spectra fit the pattern shown by other silylketenes and provide no evidence for transmission of a substituent effect of the Ph group through the silicon to the ketenyl group, as has been proposed for PhMe2Si-substituted radicals. The UV spectrum of 1 does show a longer λ and greater ∈ than for t-BuMe2SiCH=C=O, and this may indicate some interaction of the phenyl group with the ketene chromophore, while the greater reactivity of 1 in hydration compared to t-BuMe2SiCH=C=O is ascribed to the inductive effect of the phenyl. The very similar ring-opening reactivity of the bis(phenyldimethylsilyl)cyclobutenedione (6) to form 3 compared to the bis(Me3Si) analogues also provides no evidence of a significant interaction of the phenyl with the ketene. A new type of stabilized 1,8-bisketene based on the arylbis(dimethylsilyl) grouping, namely, 1,4-bis(ketenyldimethylsilyl)benzene (12), has been prepared for the first time.
Cycloadditions, III. - Reactions of Ynamines with Silylketenes
Himbert, Gerhard,Henn, Lothar
, p. 1358 - 1366 (2007/10/02)
The ynamines 1a-e react with the silyl aldoketenes 2a and b in a normal way under cycloaddition to give the allenecarboxamides 6 and in one case a cyclobutenone derivative.The presence of the silyl group in the adducts gives rise to 1,3-migrations of
