57044-58-3Relevant academic research and scientific papers
Highly efficient and chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalyzed by reusable electron-deficient [TiIV(salophen)(OTf)2]
Yadegari, Maryam,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj
experimental part, p. 332 - 338 (2012/03/12)
In the present work, highly efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalyzed by high-valent [Ti IV(salophen)(OTf)2] is reported. Under these conditions, primary, secondary and tertiary alcohols as well as phenols were silylated in short reaction times and high yields. It is noteworthy that this method can be used for chemoselective silylation of primary alcohols in the presence of secondary and tertiary alcohols and phenols. The catalyst was reused several times without loss of its catalytic activity.
Highly efficient and selective trimethylsilylation of alcohols and phenols with hexamethyldisilazane catalyzed by polystyrene-bound tin(IV) porphyrin
Gharaati, Shadab,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj
experimental part, p. 87 - 95 (2012/05/05)
In the present work, investigation of the catalytic activity of tetrakis(p-aminophenyl)porphyrinatotin(IV) trifluoromethanesulfonate, [Sn IV(TNH2PP)(OTf)2], supported on chloromethylated polystyrene in the trimethylsilylation of alcohols and phenols with hexamethyldisilazane is reported. The prepared catalyst was characterized by elemental analysis, FT-IR and diffuses reflectance UV-Vis spectroscopic methods. This catalyst was used for selective trimethylsilylation of different alcohols and phenols with HMDS, with short reaction times and high yields. Also the catalyst is of high reusability and stability, in that it was recovered several times without loss of its initial activity.
Rapid and efficient trimethylsilyl protection of hydroxyl groups catalyzed by niobium(V) chloride
Hou, Jun-Tao,Chen, Hong-Li,Zhang, Zhan-Hui
experimental part, p. 88 - 93 (2011/04/22)
An efficient and convenient procedure for the trimethylsilylation of a wide variety of alcohols, including primary, benzylic, secondary, and phenols with hexamethyldisilazane, has been developed. The reactions were carried out at room temperature in the presence of a catalytic amount of niobium(V) chloride and afforded the corresponding trimethylsilyl ethers in high to excellent yields in short time. Copyright Taylor & Francis Group, LLC.
Synthesis of 1-acylamino-1-(trimethylsiloxy)alkanes by trimethylsilyl trifluoromethanesulfonate-catalysed addition of bis(trimethylsilyl)amides to aldehydes
Johnson, A. Peter,Luke, Richard W. A.,Steele, Robert W.,Boa, Andrew N.
, p. 883 - 893 (2007/10/03)
Bis(trimethylsilyl)formamide reacts with aldehydes in refluxing chloroform, or at room temperature with catalysis by trimethylsilyl trifluoromethanesulfonate, to give 1-acylamino-1-(trimethylsiloxy)alkanes; similar results are obtained with other bis(trimethylsilyl)amides, but surprisingly not with bis(trimethylsilyl)acetamide, and addition of bis(trimethylsilyl)formamide to ketones and acetals can also be accomplished using TMS triflate as catalyst.
Formation et stabilite des carbenoides monohalogenes β-ethers
Tarhouni, R.,Kirschleger, B.,Villieras, J.
, p. C1 - C3 (2007/10/02)
The β-alkoxy monohalogenated carbenoids, C6H5CH(OSiMe3)CHXLi, can be obtained by bromine-lithium exchange from the corresponding bromohaloether in the presence of s-butllithium in a mixture of THF/ether/pentane at -130 deg C.The stability of the carbenoid (α-elimination and β-elimination) is described and discussed.
Synthesis of Trimethylsilyloxy and Hydroxy Compounds from Carbanions and Bis(trimethylsilyl)peroxide.
Camici, Lucia,Dembech, Pasquale,Ricci, Alfredo,Seconi, Giancarlo,Taddei, Maurizio
, p. 4197 - 4206 (2007/10/02)
The reactions of bis(trimethylsilyl)peroxide with alkyl, vinyl, alkynyl, aromatic and heteroaromatic anions are described.Depending on the reaction conditions, the trimethylsilyloxy derivatives can be obtained alone or together with the corresponding trimethylsilyl derivatives, which is sometimes the major product.Enolates, generated using magnesium diisopropylamide give the corresponding hydroxycarbonyl compounds in good yields.An attempt to rationalise the above results is given, emphasising the wide use of bis(trimethylsilyl)peroxide in organic synthesis as an electrophilic hydroxylation reagent.
On the Preparation of Acyl Cyanides from Aldehydes
Haerle, Helmut,Jochims, Johannes C.
, p. 1400 - 1412 (2007/10/02)
The O-silylated cyanohydrins 3 prepared from the aldehydes 1 with trimethylsilyl cyanide are oxidized photochemically or thermally with N-bromosuccinimide to afford the acyl cyanides 4a-n.Scope and limitations of the procedure are discussed.
