14629-45-9Relevant academic research and scientific papers
Formation of 1-aza-2-silacyclopentanes and unexpected products from the insertion of phenylisocyanate into 2,2-dimethyl-1-(trimethylsilyl)-1-aza-2-silacyclopentane
Herbig, Marcus,B?hme, Uwe,Schwarzer, Anke,Kroke, Edwin
, p. 11 - 19 (2018)
Substances like 3-aminopropyltriethoxysilane are often used as adhesive promoters in various formulations for coatings or to adjust the properties of siloxanes and other polymers. Cyclisation of similar substances is also interesting because of the formation of the Si-N bond. 1-Aza-2-silacyclopentanes were synthesised from 3-aminopropylalkoxysilanes by intramolecular condensation reactions and substitution reactions at the silicon atom. The products tend to undergo ring-opening polymerisation. In contrast to literature reports, they can only be isolated as N-substituted derivatives. Phenylisocyanate inserts into the Si-N bonds of cyclic aminosilanes to form seven-membered heterocycles. Furthermore, phenylisocyanate reacts with N-H bonds in the same molecule. Two insertion products were isolated, and their crystal structures were determined.
Synthetic Versatility of Lipases: Application for Si-O Bond Formation and Cleavage
Brondani, Patrícia Bulegon,Mittersteiner, Mateus,Voigt, Morgana Aline,Klinkowski, Bruna Heloisa,Riva Scharf, Dilamara,De Jesus, Paulo Cesar
supporting information, p. 477 - 485 (2019/01/10)
Several commercially available lipases were examined in a study on O-Si bond formation and cleavage applying silicon-based protecting groups and alcohols or the corresponding silyl ethers. With regard to deprotection, from silyl ether to the corresponding alcohol, only the solvent and the lipase were necessary. The influence of the protecting group, the lipase source, and the substituent was investigated to optimize the results. The TMS moiety could be removed in 24 hours of reaction at room temperature in aqueous systems (conv. up to 99%, depending on the substrate and lipase). The reverse reactions, that is, with the protection of the alcohols, were carried out in hexane using different silyl chlorides. The TMS, TES, and TBS moieties were successfully inserted in the primary and secondary alcohols without the need for dry conditions or an inert atmosphere, presenting conversions of up to 99%, depending on the substrate.
Alum: An efficient catalyst for trimethylsilylation of alcohols and phenols with hexamethyldisilazane
Yang, Xiaojuan,Liang, Jinying
experimental part, p. 228 - 230 (2012/08/07)
A highly convenient method for the trimethylsilylation of alcohols and phenols via treatment by hexamethyldisilazane in the presence of alum as a catalyst has been developed. A wide variety of hydroxyl groups were selectively protected in CH3CN under mild conditions.
Melamine-trisulfonic-acid-catalyzed trimethylsilylation of alcohols and phenols
Wu, Liqiang,Sun, Pengli,Yan, Fulin
experimental part, p. 2055 - 2060 (2011/11/30)
A highly convenient method for the trimethylsilylation of alcohols and phenols via treatment by hexamethyldisilazane in the presence ofmelamine trisulfonic acid as a catalyst has been developed. A wide variety of hydroxyl groups were selectively protected under solvent-free conditions. Copyright Taylor & Francis Group, LLC.
Silylation of alcohols and phenols with hexamethyldisilazane over highly reusable propyl sulfonic acid functionalized nanostructured SBA-15
Zareyee, Daryoush,Asghari, Rezvaneh,Khalilzadeh, Mohammad A.
experimental part, p. 1864 - 1868 (2012/02/16)
Various alcohols and phenols were trimethylsilylated in excellent yields using hexamethyldisilazane in the presence of catalytic amounts of environmentally friendly, hydrophobic, highly thermal stable, and completely heterogeneous sulfonic acid functionalized mesostructured SBA-15 in dichloromethane at ambient temperature. Primary, bulky secondary, tertiary, and phenolic hydroxyl functional groups were transformed to the corresponding trimethylsilyl ethers in excellent yields. The simple experimental procedure was accompanied by easy recovery and the catalyst was reusable (at least 18 reaction cycles); these are attractive features of this protocol.
Sulfonated ordered nanoporous carbon (CMK-5-SO3H) as an efficient and highly recyclable catalyst for the silylation of alcohols and phenols with hexamethyldisilazane (HMDS)
Zareyee, Daryoush,Ghandali, Mohammad S.,Khalilzadeh, Mohammad A.
experimental part, p. 1521 - 1525 (2012/06/18)
An environmentally friendly catalytic system for trimethylsilylation of alcohols and phenols with hexamethyldisilazane can be successfully carried out for the first time over sulfonated mesoporous carbon catalyst (CMK-5-SO 3H) in dichloromethane at ambient temperature and excellent conversions were obtained. Furthermore, the catalyst displays high activity and thermal stability (to 200 °C) and it can be reused repeatedly for at least 25 cycles without any evidence of loss of activity, confirming the stability of covalent bonding of acidic centers.
Chemoselective and catalytic trimethylsilylation of alcohols and phenols by 1,1,1,3,3,3-hexamethyldisilazane and catalytic amounts of PhMe 3N+Br3-
Ghorbani-Choghamarani, Arash,Cheraghi-Fathabad, Nasrin
experimental part, p. 1103 - 1106 (2010/12/25)
An efficient procedure for the trimethylsilylation of alcohols and phenols is presented. The combination of 1,1,1,3,3,3-hexamethyldisilazane and a catalytic amount of phenyltrimethylammonium tribromide (PhMe3N +Br3-) was found to be effective for the trimethylsilylation of alcohols and phenols. The protection reaction is very simple and homogenously performed in dichloromethane at room temperature and mild conditions.
Protection of hydroxy groups as trimethylsilyl ethers using 1,1,1,3,3,3-hexamethyldisilazane (HMDS) catalyzed BY poly(4-VINYLPYRIDINIUM TRIBROMIDE)
Ghorbani-Choghamarani, Arash,Zolfigol, Mohammad Ali,Hajjami, Maryam,Darvishi, Khorshid,Gholamnia, Laleh
experimental part, p. 607 - 615 (2011/08/05)
A very efficient procedure for the protection of alcohols and phenols is presented. The mixture of 1,1,1,3,3,3-hexamethyldisilazane (HMDS) and catalytic amounts of poly(4-vinylpyridinium tribromide) was found to be effective for the trimethylsilylation of
1,3-Dichloro-5,5-dimethylhydantoin (DCH) and trichloromelamine (TCM) as efficient catalysts for the chemoselective trimethylsilylation of hydroxyl group with 1,1,1,3,3,3-hexamethyldisilazane (HMDS) under mild conditions
Ghorbani-Choghamarani, Arash,Amani, Kamal,Zolfigol, Mohammad Ali,Hajjami, Maryam,Ayazi-Nasrabadi, Roia
experimental part, p. 255 - 260 (2009/12/06)
A highly convenient method for the trimethylsilylation of alcohols and phenols via treatment by hexamethyldisilazane in the presence of 1,3-dichloro-5,5-dimethylhydantoin (DCH) and/or trichloromelamine (TCM) as a catalyst has been developed. A wide variety of hydroxyl groups were selectively protected in CH2Cl2/CH3CN under mild conditions.
Trimethylsilylation of alcohols and phenols, and direct acetylation of silyl ethers catalyzed by Fe(ClO4)3.6H2O
Oskooie, Hossein A.,Heravi, Majid M.,Tehrani, Maryam H.,Behbahani, Farahnaz K.,Heravi, Omid M.
experimental part, p. 1729 - 1737 (2010/01/17)
In this article, a mild and efficient protocol for the trimethylsilylation of various aliphatic and benzylic alcohols and phenols with trimethylsilyl chloride using a catalytic amount of ferric perchlorate at room temperature and relatively short reaction times in good to excellent yields is reported. Direct acetylation of trimethylsilyl ethers catalyzed with Fe(ClO4)3.6H2O(0.02 mmol)/Fe(ClO4)3SiO2(0.2 g) using acetic anhydride at ambient temperature is also reported.
