5027-32-7Relevant articles and documents
ELECTROCHEMICAL OXIDATION OF 1,3-DIKETONES IN THE PRESENCE OF HYDROHALIC ACID SALTS
Elinson, M. N.,Lizunova, T. L.,Nikishin, G. I.
, p. 123 - 126 (1992)
In the presence of a mediator (sodium iodide) acetylacetone dimerizes with the formation of 3,4-diacetylhexane-2,5-dione, with a yield up to 90percent.Salts of 2-halosubstituted 1,3-diketones form more highly enolized cyclic 1,3-diketones - 1,3-cyclohexanedione and dimedone under analogous conditions, with a yield up to 90percent. Keywords: electrolysis, electrochemical oxidation, 1,3-diketones, 3,4-diacetylhexane-2,5-dione, sodium salt of 2-halosubstituted 1,3-diketones.
Direct Synthesis of Bis(acetylacetonato)nickel(II) Dihydrate and Isolation of α,α,β,β-Tetra-acetylethane as the Oxidation Product of Acetylacetone
Bhattacharjee, Manabendra N.,Chaudhuri, Mihir K.,Ghosh, Soumitra K.,Hiese, Zavei,Roy, Nirmalendu
, p. 2561 - 2562 (1983)
NiO(OH) undergoes a facile reaction with acetylacetone affording a very high yield of bis(acetylacetonato)nickel(II) dihydrate, (Ni(acac)2)2H2O, and giving α,α,β,β-tetra-acetylethane as the oxidation product of acetylacetone.
Chiral bead-like trimer of tris(2,4-pentanedionato)ruthenium(III)
Sato, Hisako,Kameda, Jun,Fukuda, Yutaka,Haga, Masa-Aki,Yamagishi, Akihiko
, p. 716 - 717 (2008)
A chiral tri-nuclear metal complex, ΔΔΔ- or ΛΛΛ-[Ru(acac)2(taet)Ru(acac)(taet)Ru(acac) 2] (acac = acetylacetonato and taet = tetraacetylethanato), was prepared and its monolayer behavior was investigated, leading to the conclusion that the bead-like character of the trimer was an essential factor in achieving stable two-dimensional molecular packing. Copyright
Alkylation of 3,4-dibromo-4-methyltetrahydropyran with diethyl malonate as a key to understanding the electronic nature of chemo- and regioselectivity of molecules
Gevorkyan,Arakelyan,Dzhandzhulyan,Mikaelyan,Petrosyan,Panosyan
, p. 134 - 140 (2005)
The reaction of 3,4-dibromo-4-methyltetrahydropyran with diethyl malonate in the presence of sodium butoxide leads to formation of the corresponding cross-coupling product rather than of tetraethyl ethane-1,1,2,2-tetracarboxylate (product of dehydrodimerization of diethyl malonate) which is formed in the presence of sodium ethoxide. An explanation was proposed, which may be regarded as a key to understanding the nature of the driving force for one- and two-electron transfer, as well as chemo- and regioselectivity of organic molecules. 2005 Pleiades Publishing, Inc.
Design and Solvothermal Synthesis of Polyoxometalate-Based Cu(II)-Pyrazolate Photocatalytic Compounds for Solar-Light-Driven Hydrogen Evolution
Chen, Yan-Xin,Hu, Ting,Liao, Mingyue,Meng, Lingyi,Wang, Tianming,Xie, Yiming,Yang, Mingxue,Zuo, Tao
supporting information, p. 13136 - 13149 (2021/09/03)
Polyoxometalates (POMs) are known for their photocatalytic hydrogen production activity, but their solubility and limited stability often restrict their practical applications. Herein, we designed and solvothermally synthesized two new Cu-H2bpz (3,3′,5,5′-tetramethyl-4,4′-bipyrazole, abbreviated as H2bpz) compounds, namely, Cu0.5(H2bpz)(NO3) (1) and Cu(Hbpz)(Cl)DMF (2), and three new polyoxometalate-based Cu(II)-pyrazolate compounds, namely, Cu(PW12O40)0.5(H2bpz)2(H2O)(OH)0.5(H2O)5.5 (3), Cu(HPMo12O40)(H2bpz)2(H2O)2(H2O)4 (4), and Cu2(SiW12O40)(H2bpz)3(H2O)3(H2O)6 (5). Compound 3 (Cu(PW12O40)0.5(H2bpz)2(H2O)(OH)0.5(H2O)5.5) exhibits the best photocatalytic activity of 44.4 μ L h-1 g-1, which may be related to the stability of compounds. Herein, the solvothermal method has been proven to be an effective method in synthesizing stable organic-inorganic hybrid compounds with soluble POMs, metal ions, and organic ligands. Thus, heterogeneous catalysts with outstanding solar-light-driven photocatalytic properties were obtained.
Modular construction of 3D coordination frameworks incorporating SiF 62- links: Accessing the significance of [M(pyrazole) 4{SiF6}] synthon
Ponomarova, Vira V.,Komarchuk, Vasiliy V.,Boldog, Ishtvan,Krautscheid, Harald,Domasevitch, Konstantin V.
, p. 8280 - 8287 (2013/10/22)
Rational combination of Cd2+ cations, bitopic pyrazole ligands, bridging SiF62- and terminal NCS- anions provide generation of 3D frameworks and precise control over connectedness of the net nodes: two-fold interpenetrated 4-connected NbO-like net (nbo) in [Cd(Me4bpz)2{NCS}2]·CH 2Cl2 (1), uninodal 5-connected noz framework in [Cd 2(Me4bpz)4{SiF6}{NCS} 2]·6CHCl3 (2), novel 5-connected binodal topology (with a point symbol of {42.55.62.7}{4 2.56.62}) in [Cd2(Me 4bpz)4{SiF6}{NCS}2]·2CH 2Cl2 (3) and 6-connected α-Po cubic nets (pcu) in [Cd(Me4bpz)2{SiF6}]·6H2O (4) and [Cd(Me4bpz)2{SiF6}]·1.5CH 2Cl2 (5) (Me4bpz = 3,3′,5,5′- tetramethyl-4,4′-bipyrazole). Hexafluorosilicate anions act as bridges between Cd ions yielding further linkage of 4-connected [Cd(Me 4bpz)2] subtopologies. Characteristic and specific interaction between SiF62- and the metal-organic portion is conditioned by a synergy of coordination and multiple strong NH...F bonds, which suggests perfect compatibility of the bipyrazole and SiF 62- linkers for the construction of 3D structures, either by pillaring of 2D layers or cross-linking of 3D frameworks. Two observed motifs, 1D [M(pyrazole)4{μ-SiF6}]n (in 4 and 5) and discrete [{M{NCS}(pyrazole)4}2{μ-SiF 6}] (in 2 and 3) are discussed as special supramolecular synthons for the framework solids. An improved large-scale and cost-effective procedure for the synthesis of the organic ligand Me4bpz is also described.
Bromophilic substitution/carbophilic substitution cascade reactions of α,α-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles
Tatar, Jovana,Markovi?, Rade,Stojanovi?, Milovan,Baranac-Stojanovi?, Marija
experimental part, p. 4851 - 4855 (2010/10/02)
α,α-Dibromo-2-methoxyacetophenone reacts, under mild reaction conditions, with C-, N- and O-nucleophiles via a bromophilic substitution/protonation/carbophilic substitution cascade process to afford α-monosubstituted-2-methoxyacetophenones in moderate to good yield. The only exception from this reaction pathway is the reaction with the anion derived from malononitrile in which 2-aroyl-1,1,3,3-tetracyanopropene is obtained.
Oxidative Coupling of 1,3-Dicarbonyl Compounds by Cerium(IV) Ammonium Nitrate
Song, Jianan,Zhang, Hao,Chen, Xianjun,Li, Xinsheng,Xu, Dongcheng
experimental part, p. 1847 - 1855 (2010/07/02)
A fast, mild, and highly efficient method for the intermolecular coupling of 1,3-dicarbonyl compounds using cerium ammonium nitrate in CH 3CN/CH3OH/H2O has been described. The procedure provided a convenient method for the synthesis of 1,4-diketone derivatives with excellent yields (up to 96%) and powerful evidence for the oxidation mechanism mediated by cerium ammonium nitrate. Copyright
Efficient selective formation of C-C single bonds and C=C double bonds by NBS-promoted oxidative coupling of β-keto esters
Wang, Zhiguo,Yin, Guodong,Chen, Aihua,Hu, Shengli,Wu, Anxin
, p. 4399 - 4405 (2008/03/14)
A new application of NBS, which results in the oxidative coupling of β-keto esters to selectively form C-C single and C=C double bonds, can be controlled by the amount of NBS and t-BuOK employed. This methodology adds a new entry to C-C single and C=C double-bond formation between active methylene groups under mild conditions with high selectivity. Copyright Taylor & Francis Group, LLC.
One-step preparation of symmetrical 1,4-diketones from α-halo ketones in the presence of Zn-I2 as a condensation agent
Ceylan, Mustafa,Guerdere, M. Burcu,Budak, Yakup,Kazaz, Cavit,Secen, Hasan
, p. 1750 - 1754 (2007/10/03)
Eleven 1,4-diphenylbutane-1,4-diones have been prepared in one step from the corresponding α-halo acetophenones under the action of Zn-I 2 as a condensation agent with moderate to high yields. The mechanistic pathway of the reaction can be explained by the Wurtz-like self-condensation of α-halo ketones. Similarly, 3-chloropentane-2,4-dione gave 3,4-diacetylhexane-2,5-dione, a Wurtz-like condensation product.
