1079-71-6Relevant articles and documents
Conformational Inversion in the Dodecahydrotriphenylene Radical Cation
Avila, David V.,Davies, Alwyn G.,Girbal, Maria L.
, p. 1999 - 2008 (1990)
The temperature dependence of the e.s.r. spectrum of the radical cation of dodecahydrotriphenylene (2) shows that the activation energy for inversion of the (benzo)cyclohexene ring is 4.8 kcal mol-1, less than it is in the octahydroanthracene radical cation (1)
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)].
Hydrogen Self-Sufficient Arene Reduction to Cyclohexane Derivatives Using a Combination of Platinum on Carbon and 2-Propanol
Sawama, Yoshinari,Mori, Misato,Yamada, Tsuyoshi,Monguchi, Yasunari,Sajiki, Hironao
, p. 3667 - 3670 (2015)
Various arenes have been hydrogenated using platinum on carbon in a 2-propanol-aqueous mixed solvent at 100 C without the addition of flammable hydrogen gas to give the corresponding cyclohexane derivatives. 2-Propanol plays a role as an efficient hydrogen source based on the platinum on carbon-catalyzed dehydrogenation.
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.
Near-monodisperse tetrahedral rhodium nanoparticles on charcoal: The shape-dependent catalytic hydrogenation of arenes
Park, Kang Hyun,Jang, Kwonho,Kim, Hae Jin,Son, Seung Uk
, p. 1152 - 1155 (2007)
The shape of things to come? Monodisperse (4.9±0.4)-nm tetrahedral rhodium nanoparticles on charcoal (/C) are compared to (4.8±0.4)-nm spherical rhodium nanoparticles on charcoal(?/C) and commercial Rh/C as a catalyst for the hydrogenation of anthracene (see picture). The former is 5.8- and 109-times more active than the latter two, respectively. It also shows a higher selectivity and excellent activity in the hydrogenation of several other arenes. (Graph Presented).
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.
Hydrogenation of Condensed Aromatic Compounds over Mesoporous Bifunctional Catalysts Following a Diels-Alder Adduct Pathway
Huyen, Pham Thanh,Krivec, Marko,Ko?evar, Marijan,Bucur, Ioana C.,Rizescu, Cristina,Parvulescu, Vasile I.
, p. 1146 - 1156 (2016)
Pt(0.5 wt %)-Al-SBA-15 and Pt(0.5 wt %)-Al-MCM-41 bifunctional catalysts were prepared by wet impregnation and investigated in the hydrogenation of anthracene and the hydrogenolysis/hydrogenation of a series of synthesized Diels-Alder adducts with anthracene and anthracene derivatives. The mesoporous texture of the investigated catalysts allowed the hydrogenation of these substrates to a large extent. In direct correlation with the size of the Pt particles, Pt-Al-SBA-15 exhibited a higher activity. Both catalysts exhibited a strong Lewis acidity associated with the presence of the Al extra-framework species. The acidity of these catalysts afforded the esterification of the reaction byproduct, that is, succinic anhydride, with methanol or ethanol, and the hydrocracking/decyclization of one hydrogenated ring to lead to 1,2,3,4-tetrahydronaphthalene derivatives. A good correlation with the calculated values of the reaction Gibbs free energy has been evidenced.
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.
A Twin-TCNQ-Type Acceptor. Synthesis of 11,11,12,12,13,13,14,14-Octacyano-1,4:5,8-anthradiquinotetramethane and Structures of the Tetraethylammonium Salts of Its Mono- and Dianion
Mitsuhashi, Tsutomu,Goto, Midori,Honda, Kazumasa,Maruyama, Yusei,Inabe, Tamotsu,et. al.
, p. 261 - 270 (1988)
The title compound (OCNAQ)was synthesized.Treatment of 1,2,3,4,5,6,7,8-octahydroanthracene with N-bromosuccinimide (NBS) under irradiation using a 100-W light bulb in refluxing CCl4 followed by dicyanomethylation with excess of NaCH(CN)2 in Me2SO gave an isomeric mixture of 1,4,5,8-tetrakis(dicyanomethyl) derivatives.The mixture was subjected by repetition of the successive bromination-dehydrobromination procedure giving OCNAQ in 20percent overall yield.The cyclic voltammogram of OCNAQ exhibits four redox waves (E1/21 0.26, E1/22 0.05, E1/23 -0.44, and E1/24 -0.53 vs.SCE in MeCN), indicating that OCNAQ is a stronger acceptor than tetracyanoquinodimethane (TCNQ, E1/21 0.17 V vs.SCE).Both 1:1 and 2:1 salts, (Et4N)(OCNAQ) and (Et4N)2(OCNAQ), were obtained from reactions of Et4NI with potassium and lithium salts of OCNAQ, respectively.The X-ray crystal analyses of these salts indicate that the TCNQ moieties are boat-shaped bent to opposite directions.With the 1:1 slat, which behaves as a semiconductor (4E-4 Ω-1 cm-1 at room temperature, Ea 0.22 eV), the OCNAQ molecules are arrayed in the segregated stacking mode, while the 2:1 salt (E-7 Ω-1 cm-1) has no columnar structure of the OCNAQ molecules.
