1079-71-6Relevant articles and documents
Bushick
, p. 79 (1971)
Rhenium complexes of di-2-pyridyl ketone, 2-benzoylpyridine and 2-hydroxybenzophenone: A structural and theoretical study
Yumata,Habarurema,Mukiza,Gerber,Hosten,Taherkhani,Nahali
, p. 89 - 103 (2013)
The reactions of di-2-pyridyl ketone (dpk), 2-benzoylpyridine (zpy) and 2-hydroxybenzophenone (Hbp) with [Re(CO)5Cl] (A) and trans-[ReOX 3(PPh3)2] (B, X = Cl, Br) were studied. The complexfac-[Re(CO)3 (dpk·OCH3)] was isolated from the reaction of A with dpk in methanol. The monoanionic tridentate chelate dpk·OCH3 was formed by the nucleophilic attack of methanol at the carbonylic carbon atom of dpk. A similar attack of water on dpk was observed in the compound cis-[ReOBr2(dpk·OH)]·2(dpkH +Br), which was formed from dpk and [ReOBr3(PPh 3)2] in acetone. The reaction of zpy with B in acetonitrile produced the complexes [ReIIIX3(zpy)(PPh 3)], but in methanol as solvent the compounds [ReOX 2(zpyH)(PPh3)] were isolated, where zpyH coordinates bidentately as the monoanionic ligand [C6H5(HC-O)C 5H4N]. With A as starting material the complexfac-[Re(CO)3(zpy)Cl] was isolated. The complexes cis-[ReOX2(bp)(PPh3)] were the products of the reaction of Hbp with B in acetonitrile; however, in methanol cis-[ReIIIBr 2 (bp)(PPh3)2] was isolated. All these complexes were characterized by conductance measurements, elemental analyses, UV-Vis, IR and NMR spectroscopy and by single crystal X-ray diffraction. DFT calculations regarding the electronic ground states show single states for all the complexes, except for the rhe-nium(III) complexes [ReIIIX 3(zpy)(PPh3)] and [ReBr2(bp)(PPh 3)2], in which the states are triplet. The DFT and experimental results are in agreement in all cases, especially the anisotropy of the Re-N bond length offac-[Re(CO)3(dpk·OCH3)] and exact O(1)-Re-O(3) angles for [ReOX2(bp)(PPh3)].
Arnold,Rondestvedt
, p. 2176 (1946)
Bushick
, p. 4085 (1968)
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Fries,Schilling
, p. 1494,1499 (1932)
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Rh(0) colloids supported on TiO2: A highly active and pertinent tandem in neat water for the hydrogenation of aromatics
Hubert, Claudie,Bile, Elodie Guyonnet,Denicourt-Nowicki, Audrey,Roucoux, Alain
, p. 1766 - 1771 (2011)
TiO2-supported Rh(0) nanoparticles were easily prepared in one step without calcination by a room temperature impregnation of the inorganic support with a prestabilized colloidal Rh(0) suspension. They are highly active and reusable catalysts for the hydrogenation of aromatics and chloroanisole derivatives in neat water with TOFs up to 33000 h-1. The comparison with the analogous silica system Rh@SiO2 was discussed showing higher catalytic selectivities and activities with Rh(0) colloids supported on TiO2.
Electroreduction in Aqueous Media, Saturation of Polycyclic Aromatics.
Kariv-Miller, Essie,Pacut, Ryszard I.
, p. 2185 - 2192 (1986)
The preparative cathodic reduction of anthracene and phenanthrene was investigated aiming at obtaining Birch-type products in aqueous solutions.Following previous reports, reductions were carried out using mercury pool cathodes and tetrabutylammonium electrolytes.Optimum conditions were found to involve tetrabutylammonium hydroxide as the electrolyte and water as the sole solvent.Reactions were carried out in a simple cell, using constant current and the products were isolated and identified.Anthracene formed initially 9,10-dihydroanthracene which reduced with additional charge transfer to 1,4,5,8,9,10-hexahydroanthracene in high yield.To obtain more saturated anthracene derivatives, a process was developed which involves a "one pot" reduction-isomerization-reduction sequence.Anthracene was electrolyzed first to completion, the product was isomerized by reflux in the electrolyte solution (in the cell but without charge transfer) and was then electrolyzed again.Using this process 1,2,3,4,5,6,7,8-octahydroanthracene and 1,2,3,4,5,6,7,8,9,10-decahydroanthracene were formed in significant yields.Reduction of phenanthrene resulted in mixtures of high saturated derivatives without need for isomerization steps.The major products varied with the amount of charge transferred from dihydrophenanthrene (3F/mol) to octahydrophenanthrene (10F/mol) and decahydrophenanthrene (20F/mol).In general it was shown that cathodic hydrogenation of polycyclic aromatics is possible in aqueous solutions.The products resemble those obtained by metal-ammonia or amine reductions.The degree of saturation can be controlled by the amount of charge transferred and can be increased by a combination of alternate reductions and isomerization.
Synthesis of tetraline derivatives through depolymerization of polyethers with aromatic compounds using a heterogeneous titanium-exchanged montmorillonite catalyst
Maeno, Zen,Torii, Hiroyuki,Yamada, Shota,Mitsudome, Takato,Mizugaki, Tomoo,Jitsukawa, Koichiro
, p. 89231 - 89233 (2016)
A novel depolymerization of poly(tetramethylene glycol) (PTMG) with benzene to tetralin using titanium-exchanged montmorillonite (Ti4+-mont) as a solid acid catalyst is described. This catalyst is applicable to depolymerization of PTMG with some aromatic compounds. This is the first demonstration of the potential use of PTMG as a C4 synthon for organic synthesis.
One-pot synthesis of tetralin derivatives from 3-benzoylpropionic acids: Indium-catalyzed hydrosilylation of ketones and carboxylic acids and intramolecular cyclization
Sakai, Norio,Kobayashi, Taichi,Ogiwara, Yohei
, p. 1503 - 1505 (2015)
This reducing system was composed of a small amount (1 mol%) of In(OAc)3, Me2PhSiH, and I2 that effectively catalyzed the hydrosilylation of two different carbonyl groups, a ketone and a carboxylic acid found in 3-benzoylpropionic acids, followed by a subsequent intramolecular cyclization that led to the one-pot preparation of tetralin derivatives.
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Orchin
, p. 535,537 (1944)
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Electron-Transfer Reactions in the Marcus Inverted Region. Charge Recombination versus Charge Shift Reactions
Gould, Ian R.,Moser, Jacques E.,Armitage, Bruce,Farid, Samir,Goodman, Joshua L.,Herman, Michael S.
, p. 1917 - 1919 (1989)
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Hydrogenation of naphthalene and anthracene on Pt/C catalysts
Kalenchuk,Koklin,Bogdan,Kustov
, p. 1406 - 1411 (2018)
Hydrogenation of naphthalene and anthracene deposited on Sibunit and active carbon was studied. The reactions were carried out at a temperature of 280 °C and a pressure of 90 atm. The directions for the complete hydrogenation of the investigated substrates were studied. Correlations between the structures of naphthalene and anthracene and their activity in hydrogen absorption are presented. The hydrogenation rates decrease as the substrate is saturated with hydrogen.
Ligand-enabled and magnesium-activated hydrogenation with earth-abundant cobalt catalysts
Han, Bo,Jiao, Hongmei,Ma, Haojie,Wang, Jijiang,Zhang, Miaomiao,Zhang, Yuqi
, p. 39934 - 39939 (2021/12/31)
Replacing expensive noble metals like Pt, Pd, Ir, Ru, and Rh with inexpensive earth-abundant metals like cobalt (Co) is attracting wider research interest in catalysis. Cobalt catalysts are now undergoing a renaissance in hydrogenation reactions. Herein, we describe a hydrogenation method for polycyclic aromatic hydrocarbons (PAHs) and olefins with a magnesium-activated earth-abundant Co catalyst. When diketimine was used as a ligand, simple and inexpensive metal salts of CoBr2in combination with magnesium showed high catalytic activity in the site-selective hydrogenation of challenging PAHs under mild conditions. Co-catalyzed hydrogenation enabled the reduction of two side aromatics of PAHs. A wide range of PAHs can be hydrogenated in a site-selective manner, which provides a cost-effective, clean, and selective strategy to prepare partially reduced polycyclic hydrocarbon motifs that are otherwise difficult to prepare by common methods. The use of well-defined diketimine-ligated Co complexes as precatalysts for selective hydrogenation of PAHs and olefins is also demonstrated.
Chromium- and Cobalt-Catalyzed, Regiocontrolled Hydrogenation of Polycyclic Aromatic Hydrocarbons: A Combined Experimental and Theoretical Study
Han, Bo,Ma, Pengchen,Cong, Xuefeng,Chen, Hui,Zeng, Xiaoming
supporting information, p. 9018 - 9026 (2019/06/13)
Polycyclic aromatic hydrocarbons are difficult substrates for hydrogenation because of the thermodynamic stability caused by aromaticity. We report here the first chromium- and cobalt-catalyzed, regiocontrolled hydrogenation of polycyclic aromatic hydrocarbons at ambient temperature. These reactions were promoted by low-cost chromium or cobalt salts combined with diimino/carbene ligand and methylmagnesium bromide and are characterized by high regioselectivity and expanded substrate scope that includes tetracene, tetraphene, pentacene, and perylene, which have rarely been reduced. The approach provides a cost-effective catalytic protocol for hydrogenation, is scalable, and can be utilized in the synthesis of tetrabromo- and carboxyl-substituted motifs through functionalization of the hydrogenation product. The systematic theoretical mechanistic modelings suggest that low-valent Cr and Co monohydride species, most likely from zerovalent transition metals, are capable of mediating these hydrogenations of fused PAHs.
