930-68-7Relevant articles and documents
Bersohn,M.
, p. 2136 - 2138 (1961)
Coordination chemistry of 1,3-bis(2-pyridylimino)- and 1,3-bis-(2- thiazolylimino)isoindole copper complexes: Investigation of their catalytic behavior in oxidation reactions
Meder, Markus B.,Gade, Lutz H.
, p. 2716 - 2722 (2004)
The copper complexes [Cu(4-MeBPI)(OAc)] (4), [Cu(4-Me-10-tBuBPI)(OAc)] (5) and [Cu(BTI)(OAc)] (6) [BPI = 1,3-bis(2-pyridylimino)isoindole, BTI = 1,3-bis(2-thiazolylimino)isoindole] were prepared by reaction of the protio ligands with copper(II) acetate. Compounds 4 and 6 were characterized by X-ray diffraction, establishing distorted square-planar coordination geometries of the copper ions. Two monoclinic modifications of 6 (6a and 6b) were found, both crystallizing in the space group P21/c, but possessing different cell parameters. In contrast to 6a, which is monomeric in the crystal, the second monoclinic modification 6b has a more complicated crystal structure, which is composed of both monomeric complex units such as those found in 6a and infinite chains of coordination polymers. The copper atoms in the polymeric chains of 6b display fivefold coordination and a ligand polyhedron that is an intermediate form between a trigonal-bi-pyramidal and a square-pyramidal geometry. The allylic peroxylation of cyclohexene with tBuOOH (70% aqueous solution) catalyzed by 4 and 6 (0.17 mol %) gave tert-butylperoxy-3-cyclohexene with selectivities of 86% and 80% (based on cyclohexene) and turnover frequencies of 63 h -1 and 18 h-1, respectively. The peroxylation reaction is thought to proceed according to a Haber-Weiss radical chain mechanism. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Assessment of the Antioxidative and Prooxidative Activities of Two Aminoreductones Formed during the Maillard Reaction: Effects on the Oxidation of β-Carotene, Nα-Acetylhistidine, and cis-Alkenes
Pischetsrieder, Monika,Rinaldi, Francesco,Gross, Ursula,Severin, Theodor
, p. 2945 - 2950 (1998)
In short-time-heated mixtures of lactose and Nα-acetyllysine 1-[N∈-(N α-acetyllysinyl)]-1,2-dehydro1,4-dideoxy-3-hexulose (C6-AR) is formed as main product, whereas 3-hydroxy-4-(alkylamino)-3-buten-2-one (C
Polyoxometalate-molybdenylacetylacetonate hybrid complex: A reusable and efficient catalyst for oxidation of alkenes with tert-butylhydroperoxide
Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Javadi, Maedeh Moshref
, p. 244 - 249 (2010)
The hybrid complex consist of molybdenylacetylacetonate complex covalently linked to a lacunary Keggin-type polyoxometalate, K8[SiW11O39] (POM), was synthesized and characterized by elemental analysis, SEM, XRD, diffuse re
Synthesis and characterization of gold nanoparticles supported on thiol functionalized chitosan for solvent-free oxidation of cyclohexene with molecular oxygen
Ghiaci, Mehran,Dorostkar, Nasim,Martínez-Huerta, M. Victoria,Fierro,Moshiri, Parisa
, p. 340 - 349 (2013)
The selective liquid phase oxidation of cyclohexene to 2-cyclohexe-1-one and 1,2-cyclohexanediol has been investigated over gold nanoparticles (GNPs) with molecular oxygen in a solvent-free condition. The gold nanoparticles were immobilized on thiolated chitosan derivative (TChD), by grafting thiol groups on the support. The catalyst was characterized by XPS, N2 adsorption/desorption, TEM, FT-IR and UV-vis spectroscopy. TEM results show that the majority of Au particles have diameters in the range of 3-6 nm. X-ray photoelectron spectroscopy (XPS) revealed the coexistence of both oxidized and metallic gold species on the surface of TChD. The results show that the catalytic performance of GNPs/TChD is quite remarkable and the catalytic activity over recycled catalyst remains at a high level after at least 4 cycles. Activity tests were carried out in an autoclave at 80 C without any solvent. In order to obtain maximum conversion, the reaction parameters such as reaction temperature and time were optimized. Under optimized conditions, a maximum of 87% conversion and 70% selectivity was achieved with the GNPs/TChD catalyst.
Silylated layered double hydroxide nanosheets prepared by a large-scale synthesis method as hosts for intercalation of metal complexes
Guo, Wenya,Zhao, Yuan,Zhou, Fan,Yan, Xiaoliang,Fan, Binbin,Li, Ruifeng
, p. 101 - 108 (2016)
We present a novel strategy for preparing silylated MgAl layered double hydroxide (LDH) intercalated with metal complexes with the purpose of improving the catalytic activity of the intercalated active species. This strategy involves preparing the exfolia
Palladium-catalyzed alkylation of allylic nitrates derived from ceric ammonium nitrate promoted oxidative addition of trimethylsilyloxy-cyclopropanes to 1,3-butadiene
Paolobelli, Anna Belli,Gioacchinia, Fabio,Ruzziconi, Renzo
, p. 6333 - 6336 (1993)
Silyloxycyclopropanes are easily oxidized by eerie ammonium nitrate to generate β-carbonylalkyl radicals which are able to add to 1,3-butadiene to give a mixture of 4-(γ-carbonylalkyl)-substituted 3-nitroxy-1-butenes and 4-(γ-carbonylalkyl) substituted (E)-1-nitroxy-2-butenes (1,2- and 1,4-adducts) in ca. 1:1 molar ratio. The crude mixture, subjected to palladium-catalyzed alkylation by a variety of carbon nucleophiles, affords mainly δ,g3-unsaturated carbonyl compounds with high regio- and stereoselectivity and in satisfactory overall yield.
Palladium-catalyzed stereospecific 1,4-hydrogen migration of cis-cyclohex- 2-en-1,4-diol systems
Takano,Moriya,Kamikubo,Hiroya,Ogasawara
, p. 8485 - 8488 (1993)
It has been revealed that the generation of 2-cyclohexenones from cis- 1,4-dihydroxycyclohexene derivatives under PdCl2(PPh3)2-HCO2NH4 system takes place in an intramolecular pathway involving unprecedented mode of suprafacial 1,4-hydrogen migration across the 1,4-allylic centers.
Conversion of lactones to the higher homologous α,β-unsaturated lactones via hypervalent iodine oxidation of 1-trimethylsilyloxy-2-oxa[n.1.0] cycloalkines
Moriarty,Vaid,Hopkins,Vaid,Prakash
, p. 197 - 200 (1990)
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Oxygen Atom Transfer Mechanism for Vanadium-Oxo Porphyrin Complexes Mediated Aerobic Olefin Epoxidation
Han, Qi,Huang, Jia-Ying,Ji, Hong-Bing,Liu, Xiao-Hui,Tao, Lei-Ming,Xue, Can,Yu, Hai-Yang,Zhou, Xian-Tai,Zou, Wen
, p. 115 - 122 (2021/12/04)
The development of catalytic aerobic epoxidation by numerous metal complexes in the presence of aldehyde as a sacrificial reductant (Mukaiyama epoxidation) has been reported, however, comprehensive examination of oxygen atom transfer mechanism involving free radical and highly reactive intermediates has yet to be presented. Herein, meso-tetrakis(pentafluorophenyl) porphyrinatooxidovanadium(IV) (VOTPFPP) was prepared and proved to be efficient toward aerobic olefin epoxidation in the presence of isobutyraldehyde. In situ electron paramagnetic resonance spectroscopy (in situ EPR) showed the generation, transfer pathways and ascription of free radicals in the epoxidation. According to the spectral and computational studies, the side-on vanadium-peroxo complexes are considered as the active intermediate species in the reaction process. In the cyclohexene epoxidation catalyzed by VOTPFPP, the kinetic isotope effect value of 1.0 was obtained, indicating that epoxidation occurred via oxygen atom transfer mechanism. The mechanism was further elucidated using isotopically labeled dioxygen experiments and density functional theory (DFT) calculations.
Bidentate Nitrogen-Ligated I(V) Reagents, Bi(N)-HVIs: Preparation, Stability, Structure, and Reactivity
Xiao, Xiao,Roth, Jessica M.,Greenwood, Nathaniel S.,Velopolcek, Maria K.,Aguirre, Jordan,Jalali, Mona,Ariafard, Alireza,Wengryniuk, Sarah E.
, p. 6566 - 6576 (2021/05/06)
Hypervalent iodine(V) reagents are a powerful class of organic oxidants. While the use of I(V) compounds Dess-Martin periodinane and IBX is widespread, this reagent class has long been plagued by issues of solubility and stability. Extensive effort has been made for derivatizing these scaffolds to modulate reactivity and physical properties but considerable room for innovation still exists. Herein, we describe the preparation, thermal stability, optimized geometries, and synthetic utility of an emerging class of I(V) reagents, Bi(N)-HVIs, possessing datively bound bidentate nitrogen ligands on the iodine center. Bi(N)-HVIs display favorable safety profiles, improved solubility, and comparable to superior oxidative reactivity relative to common I(V) reagents. The highly modular synthesis and in situ generation of Bi(N)-HVIs provides a novel and convenient screening platform for I(V) reagent and reaction development.
Instant Cyclohexene Epoxidation Over Ni-TUD-1 Under Ambient Conditions
Hamdy, Mohamed S.,Al-Zaqri, Nabil,Sahlabji, Taher,Eissa, Murad,Haija, Mohammad Abu,Alhanash, Abdullah M.,Alsalme, Ali,Alharthi, Fahad A.,Abboud, Mohamed
, p. 1612 - 1622 (2020/10/14)
Abstract: To avoid the aggregation problem and activity loss of nickel oxide (NiO) nanoparticles (NPs) in organic reactions, NiO NPs were incorporated into TUD-1 mesoporous material. One-step sol–gel preparation was applied to prepare four samples of Ni incorporated in TUD-1 silica matrix with different Ni content. The four samples with Si/Ni ratio = 100, 50, 20, and 10 were characterized by means of elemental analysis, powder X-ray diffraction (XRD), Raman spectroscopy, N2 sorption measurements, scanning electron microscopy (SEM), thermal gravimetric analysis (TGA), and high-resolution transmission electron microscopy (HR-TEM). The characterization analysis showed that Ni2+ ions were incorporated into the silica matrix as individual isolated active sites at Ni content smaller than 2 wt%, and as nanoparticles of NiO when the loading is equal to or higher than 5 wt%. The size of NiO NPs inside the silica matrix is highly dependent on the Ni content, i.e. the size of NiO NPs when the loading was 5 wt% and 10 wt% was 5–10 and 40–60?nm, respectively. The catalytic activity of Ni-TUD-1 was investigated in the epoxidation reaction of cyclohexene at room temperature by using meta-chloroperoxybenzoic acid (m-CPBA) as an oxidant. The obtained results showed that Ni-TUD-1 exhibited superior activity in which 100% conversion of cyclohexene with > 90% selectivity towards cyclohexene oxide was obtained instantly. This result was found to benchmark not only the unsupported NiO nanoparticles, but also the reported catalysts at similar conditions. Graphic Abstract: [Figure not available: see fulltext.].
