14289-64-6Relevant academic research and scientific papers
An Ion-Pairing Approach to Stereoselective Metal-Free Ring-Opening Metathesis Polymerization
Yang, Xuejin,Gitter, Sean R.,Roessler, Allison G.,Zimmerman, Paul M.,Boydston, Andrew J.
, p. 13952 - 13958 (2021)
Stereochemistry can have a profound impact on polymer and materials properties. Unfortunately, straightforward methods for realizing high levels of stereocontrolled polymerizations are often challenging to achieve. In a departure from traditional metal-me
Production of allyl compound (by machine translation)
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Paragraph 0046; 0068; 0069, (2019/07/17)
[Problem] Chlorine contamination risk of the reaction mass, ester reaction agent, and, because the reaction solution cannot be re-used without using dissolved transition metal complex catalyst, metal oxide catalyst obtained by using a relatively simple operation, a relatively high yield or production or synthesis of allyl compounds, and a manufacturing method for a metal oxide catalyst used in the synthesis. [Solution] Allyl alcohol, alcohols, phenol compounds such as allyl group is applied to the dehydration is introduced, allyl ethers, allyl thioether compound such as allyl compounds such as allyl manufacturing method, and an alcohol, the compound is mixed in the liquid, at least one of titania and zirconia obtained by mixing molybdenum compound, titania and/or zirconia on the surface of the molybdenum oxide film formed using the metal oxide catalyst. Figure 1 [drawing] (by machine translation)
Nano-dispersed platinum(0) in organically modified silicate matrices as sustainable catalysts for a regioselective hydrosilylation of alkenes and alkynes
Duke, Brett J.,Akeroyd, Evan N.,Bhatt, Shreeja V.,Onyeagusi, Chibueze I.,Bhatt, Shreya V.,Adolph, Brandy R.,Fotie, Jean
, p. 11782 - 11795 (2018/07/25)
Nano-dispersed platinum(0) particles stabilized in a range of organically modified silicate (ORMOSIL) matrices are investigated as sustainable catalysts for the hydrosilylation of alkenes and alkynes. In this study, five different siloxane matrices including triethoxysilane (HTEOS), methyltriethoxysilane (MTES), ethyltriethoxysilane (ETES), triethoxyvinylsilane (TEVS) and propyltriethoxysilane (PTES) are investigated, and the distribution of the metal particles in these materials analyzed by transition electron microscopy (TEM). The particles appeared to be generally of a small size, with a diameter of ca. 2-5 nm in each of these catalysts, however the distribution is not equally uniform from one matrix to the other. HTEOS, MTES and ETES that respectively carry a hydrogen, a methyl and an ethyl group on the triethoxysilane moiety, displayed a more uniform distribution, while particles appeared to be more scattered in the remaining matrices. Catalysts with a uniform particles distribution produced higher and consistent yields, while those with poor particles distribution produced lower and almost random yields, suggesting that the uniformity in particle distribution, and by extension the nature of the siloxane matrix, are important for the catalytic properties of these materials. The scope of the reaction was broadened to a range of olefins, with a goal of investigating the tolerability of the reaction toward a number of reactive functional groups, resulting in the preparation of 28 compounds. This catalytic system also enabled the hydrosilylation of a limited number of alkynes under the optimized reaction conditions.
Versatile etherification of alcohols with allyl alcohol by a titanium oxide-supported molybdenum oxide catalyst: Gradual generation from titanium oxide and molybdenum oxide
Kon, Yoshihiro,Fujitani, Tadahiro,Nakashima, Takuya,Murayama, Toru,Ueda, Wataru
, p. 4618 - 4625 (2018/09/29)
Etherification using allyl alcohol to produce allyl ether via dehydration is a fundamental technique for producing fine chemicals that can be applied to electronic devices. We demonstrate a sustainable method to synthesize allyl ethers from allyl alcohol with various alcohols up to a 91% yield, with water as the sole by-product. In this reaction, the active catalyst is gradually generated as the reaction proceeds through the simple mixing of TiO2 and MoO3. The dispersion of MoO3 on the spent catalyst has been observed by XRD, HAADF-STEM, and STEM-EDS mapping. This catalyst shows excellent catalytic activity by virtue of the highly dispersed nature of MoO3 supported on TiO2, which is reusable at least five times. According to a mechanistic study including the measurement of XPS of MoO3 on TiO2 and control experiments using SiO2 and Al2O3 supports, the suitable reducibility of MoO3 to coordinate the allyl moiety on TiO2 seems to be a key factor for high-yielding syntheses of various allyl ethers even under heterogeneous reaction conditions. The reaction mechanism is considered to be as follows: σ-allyl species are formed from dehydration of the allyl alcohol, followed by a nucleophilic attack by another alcohol against the σ-allyl carbon to give allyl ethers. The developed catalytic system should be suitable for easily handled syntheses of allyl ethers due to the employment of commercially available MoO3 and TiO2 with halide- and organic solvent-free reaction conditions.
A mild copper catalyzed method for the selective deprotection of aryl allyl ethers
Hemming, David S.,Talbot, Eric P.,Steel, Patrick G.
supporting information, p. 17 - 20 (2016/12/23)
Copper boryl reagents enable the selective cleavage of aryl allyl ethers to the corresponding phenols in good to moderate yields.
Copper-Catalyzed Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling
Thapa, Surendra,Basnet, Prakash,Giri, Ramesh
supporting information, p. 5700 - 5703 (2017/05/04)
We present a strategy that difunctionalizes unactivated olefins in 1,2-positions with two carbon-based entities. This method utilizes alkyl/arylzinc reagents derived from olefin-tethered alkyl/aryl halides that undergo radical cyclization to generate C(sp3)-Cu complexes in situ, which are intercepted with aryl and heteroaryl iodides. A variety of (arylmethyl)carbo- and heterocycles (N, O) can be synthesized with this new method.
Hydrogen-bond-activated palladium-catalyzed allylic alkylation via allylic alkyl ethers: Challenging leaving groups
Huo, Xiaohong,Quan, Mao,Yang, Guoqiang,Zhao, Xiaohu,Liu, Delong,Liu, Yangang,Zhang, Wanbin
supporting information, p. 1570 - 1573 (2014/04/17)
C-O bond cleavage of allylic alkyl ether was realized in a Pd-catalyzed hydrogen-bond-activated allylic alkylation using only alcohol solvents. This procedure does not require any additives and proceeds with high regioselectivity. The applicability of this transformation to a variety of functionalized allylic ether substrates was also investigated. Furthermore, this methodology can be easily extended to the asymmetric synthesis of enantiopure products (99% ee).
Scope of the allylation reaction with [RuCp(PP)]+ catalysts: Changing the nucleophile or allylic alcohol
Van Rijn, Jimmy A.,Guijt, Marieke C.,De Vries, Dwight,Bouwman, Elisabeth,Drent, Eite
experimental part, p. 212 - 219 (2012/04/17)
The scope of the dehydrative allylation reaction using allyl alcohol as allyl donor with [RuCp(PP)]+ complexes as catalysts is explored. Aliphatic alcohols are successfully allylated with allyl alcohol or diallyl ether, obtaining high selectivity for the alkyl allyl ether. The reactivity of aliphatic alcohols is in the order of primary > secondary tertiary. The tertiary alcohol 1-adamantanol reacts extremely slowly in the absence of strong acid, but when HOTs is added, reasonable yields of 1-adamantyl allyl ether are obtained. The alkyl allyl ether is found to be the thermodynamically favored product over diallyl ether. Apart from alcohols, thiols and indole are also efficiently allylated, while aniline acts as a catalyst inhibitor. Allylation reactions with various substituted allylic alcohols give products with retention of the substitution pattern. It is proposed that a Ru(IV) σ-allyl species plays a key role in the mechanism of these allylation reactions.
Isomerization of allyl ethers initiated by lithium diisopropylamide
Su, Chicheung,Williard, Paul G.
supporting information; experimental part, p. 5378 - 5381 (2011/02/27)
Lithium diisopropylamide (LDA) promotes virtually quantitative conversion of allylic ethers to (Z)-propenyl ethers. It was discovered that allylic ethers can be isomerized efficiently with very high stereoselectivity to (Z)-propenyl ethers by LDA in THF a
PROCESS FOR THE PREPARATION OF AN ALLY ALKYL EHTER BY CATALYTIC ALLYATION
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Page/Page column 9; 10, (2010/08/09)
The invention provides a process for the preparation of an allyl alkyl ether comprising the allylation of an aliphatic hydroxyl containing compound with an allyl source in the presence of a catalyst, wherein the catalyst is a transition metal complex with a phosphine ligand, wherein the allylation is carried out in the presence of an acid in an amount of at least 0.1 mol% calculated on the aliphatic hydroxyl containing compound. This invention further provides a process for the preparation of epoxy resins wherein as intermediate use is made of the allyl alkyl ethers prepared by the process of the invention.
