1687-29-2Relevant articles and documents
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Siegel,McCaleb
, p. 3655,3657 (1959)
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Synthesis of Dimethyl 1,2-Cycloalkanedicarboxylates by Electrochemical Cyclization of Dimethyl α,α-Dibromoalkanedioates Using a Copper Anode
Tokuda, Masao,Hayashi, Atsushi,Suginome, Hiroshi
, p. 2590 - 2592 (1991)
The electrochemical cyclization of dimethyl α,α'-dibromoalkanedioates by making use of a platinum cathode and a copper anode in the presence of sodium iodide gave three- to six-membered dimethyl 1,2-cycloalkanedicarboxylates in good yields.
Highly-efficient Ru/Al-SBA-15 catalysts with strong Lewis acid sites for the water-assisted hydrogenation of: P -phthalic acid
Ahamad, Tansir,Kankala, Ranjith Kumar,Mao, Cong,Matsagar, Babasaheb M.,Wu, Kevin C.-W.,Yang, Yucheng,Zhang, Xueqin,Zheng, Jingwei
, p. 2443 - 2451 (2020/05/14)
Ruthenium nanoparticles supported onto aluminum-doped mesoporous silica catalysts (Ru/Al-SBA-15) are fabricated using hydrothermal and impregnation methods for catalysis application. The Ru/Al-SBA-15-3 catalyst at a Si/Al molar ratio of 3 exhibited excellent catalytic performance for the hydrogenation of p-phthalic acid with high conversion efficiency (100.0%) and cis-isomer selectivity (84.0%) in water. Moreover, this system displays exceptional stability and recyclability through preserving the conversion efficiency, as well as a cis-isomer selectivity of 90.2 and 83.3%, respectively, after reusing it fourteen times. Such an exceptional system can also be ideal for the hydrogenation of aromatic dicarboxylic acids and their ester derivatives in water. Strong Lewis acid sites due to doped Al species play significant roles in the hydrogenation reaction. Moreover, isotope labeling studies indicated that water molecules effectively participated in the hydrogenation reaction. Hydrogen and water contributed half of the hydrogen atoms for this hydrogenation reaction. In the end, a plausible mechanistic pathway for the hydrogenation of p-phthalic acid using the Ru/Al-SBA-15-3 catalyst in water is proposed.
Epimerization of Tertiary Carbon Centers via Reversible Radical Cleavage of Unactivated C(sp3)-H Bonds
Wang, Yaxin,Hu, Xiafei,Morales-Rivera, Cristian A.,Li, Guo-Xing,Huang, Xin,He, Gang,Liu, Peng,Chen, Gong
supporting information, p. 9678 - 9684 (2018/07/21)
Reversible cleavage of C(sp3)-H bonds can enable racemization or epimerization, offering a valuable tool to edit the stereochemistry of organic compounds. While epimerization reactions operating via cleavage of acidic C(sp3)-H bonds, such as the Cα-H of carbonyl compounds, have been widely used in organic synthesis and enzyme-catalyzed biosynthesis, epimerization of tertiary carbons bearing a nonacidic C(sp3)-H bond is much more challenging with few practical methods available. Herein, we report the first synthetically useful protocol for the epimerization of tertiary carbons via reversible radical cleavage of unactivated C(sp3)-H bonds with hypervalent iodine reagent benziodoxole azide and H2O under mild conditions. These reactions exhibit excellent reactivity and selectivity for unactivated 3° C-H bonds of various cycloalkanes and offer a powerful strategy for editing the stereochemical configurations of carbon scaffolds intractable to conventional methods. Mechanistic study suggests that the unique ability of N3? to serve as a catalytic H atom shuttle is critical to reversibly break and reform 3° C-H bonds with high efficiency and selectivity.
Synthesis of phthalate-free plasticizers by hydrogenation in water using RhNi bimetallic catalyst on aluminated SBA-15
Phan-Vu, Duc-Ha,Tan, Chung-Sung
, p. 18178 - 18188 (2017/04/04)
In this study, rhodium-nickel bimetallic nanoparticles loaded on aluminated silica (RhNi/Al-SBA-15) were used as catalysts for the hydrogenation of phthalate in water to produce environmentally acceptable non-phthalate plasticizers. Chemical fluid deposition (CFD) was used to dope metals onto the aluminated silica support, which helped to create a uniform structure of RhNi on Al-SBA-15. The introduction of Ni helped to reduce the use of expensive Rh and increase the number of metal active sites by reducing the bimetallic nanoparticle size. Aluminated SBA-15 not only acted as the support for the RhNi bimetallic catalyst but also enhanced the reaction efficiency by introducing Br?nsted and Lewis acid sites and the absorption of phthalates on the catalyst in water. The physicochemical properties of prepared catalysts were characterized by N2 adsorption-desorption isotherm, X-ray diffraction (XRD), in situ diffuse reflectance infrared Fourier transform spectroscopy (DRIFTS), Scanning electron microscopy (SEM), and Transmission electron microscopy (TEM). The catalytic performance of the synthesized catalysts was evaluated with the hydrogenation of dimethyl phthalate (DMP). Despite the low solubility of DMP in water, the hydrogenation using Rh0.5Ni1.5/Al-SBA-15 was carried out with an 84.4% reaction yield (cis-?:?trans- = 97.5?:?2.5) at 80 °C using 1000 psi of H2 after 2 h.