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Cas Database

141-05-9

141-05-9

Identification

  • Product Name:Diethyl maleate

  • CAS Number: 141-05-9

  • EINECS:205-451-9

  • Molecular Weight:172.181

  • Molecular Formula: C8H12O4

  • HS Code:29171990

  • Mol File:141-05-9.mol

Synonyms:2-Butenedioicacid (2Z)-, diethyl ester (9CI);2-Butenedioic acid (Z)-, diethyl ester;Maleicacid, diethyl ester (6CI,8CI);(2Z)-2-Butenedioic acid diethyl ester;Diethyl(Z)-2-butenedioate;2-Butenedioicacid (2Z)-, 1,4-diethyl ester;Ethyl maleate;Staflex DEM;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H317 May cause an allergic skin reaction

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 150 Articles be found

Maleates from diazoacetates and dilactones from head-to-head dimerisation of alkenyl diazoacetates using Grubbs' 2nd-generation ruthenium carbene catalyst

Hodgson, David M.,Angrish, Deepshikha

, p. 4902 - 4904 (2005)

Grubbs' 2nd-generation ruthenium carbene catalyst homocouples diazoacetates to maleates and also catalyses head-to-head dimerisation of alkenyl diazoacetates giving dienyl dilactones. The Royal Society of Chemistry 2005.

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Wulfman et al.

, p. 1241,1243 (1976)

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Catalytic Formation of Aziridines from Imines and Diazoacetates

Rasmussen, Kaare G.,Joergensen, Karl Anker

, p. 1401 - 1402 (1995)

A catalytic method for the preparation of aziridines from imines and diazoacetate is developed using copper complexes as catalyst; the synthetic, diastereo- and enantio-selective scope of the reaction are presented.

REACTION OF ETHYL DIAZOACETATE WITH ALLYLAMINES CATALYZED BY COPPER AND RHODIUM COMPLEXES

Dzhemilev, U. M.,Fakhretdinov, R. N.,Marvanov, R. M.,Nefedov, O. M.

, p. 539 - 543 (1984)

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Cyclopropanation of alkenes with ethyl diazoacetate catalysed by ruthenium porphyrin complexes

Galardon, Erwan,Le Maux, Paul,Simonneaux, Gerard

, p. 927 - 928 (1997)

Ruthenium porphyrin complexes are active catalysts for the cyclopropanation of styrene derivatives by ethyl diazoacetate with good to very good diastereoselectivity; moderate enantiomeric excesses (34%) are observed using a chiral porphyrin as catalyst.

Confinement of Fe-Al-PMOF catalytic sites favours the formation of pyrazoline from ethyl diazoacetate with an unusual sharp increase of selectivity upon recycling

Abeykoon, Brian,Devic, Thomas,Grenèche, Jean-Marc,Fateeva, Alexandra,Sorokin, Alexander B.

, p. 10308 - 10311 (2018)

The catalytic properties of a chemically stable iron porphyrin MOF were evaluated in a reaction with ethyl diazoacetate. In contrast to its homogeneous counterpart, an Fe-porphyrin-MOF features a different reaction pathway leading to the formation of pyrazoline due to the confinement of catalytic sites within the MOF network. Unexpectedly, a sharp increase of the selectivity from 35% (run 1) to 86% (run 5) occurs upon catalyst recycling.

-

Werner,Richards

, p. 4976 (1968)

-

-

Sato et al.

, p. 1833 (1973)

-

-

Stafford et al.

, p. 656,658 (1954)

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Synthesis and Characterization of Germanium, Tin, Phosphorus, Iron, and Rhodium Complexes of Tris(pentafluorophenyl)corrole, and the Utilization of the Iron and Rhodium Corroles as Cyclopropanation Catalysts

Simkhovich, Liliya,Mahammed, Atif,Goldberg, Israel,Gross, Zeev

, p. 1041 - 1055 (2001)

The germanium(IV), tin(IV), and phosphorus(V) complexes of tris(pentafluorophenyl)corrole were prepared and investigated by electrochemistry for elucidation of the electrochemical HOMO-LUMO gap of the corrole and the spectroscopic characteristics of the corrole ? radical cation. This information was found to be highly valuable for assigning the oxidation states in the various iron corroles that were prepared. Two iron corroles and the rhodium(I) complex of an N-substituted corrole were fully characterized by X-ray crystallography and all the transition metal corroles were examined as cyclopropanation catalysts. All iron (except the NO-ligated) and rhodium corroles are excellent catalysts for Cyclopropanation of styrene, with the latter displaying superior selectivities. An investigation of the effect of the oxidation state of the metal and its ligands leads to the conclusion that for iron corroles the catalytically active form is iron(III), while all accesible oxidation states of rhodium are active.

Mechanochemical defect engineering of HKUST-1 and impact of the resulting defects on carbon dioxide sorption and catalytic cyclopropanation

Barozzino-Consiglio, Gabriella,Filinchuk, Yaroslav,Grégoire, Nicolas,Hermans, Sophie,Steenhaut, Timothy

, p. 19822 - 19831 (2020)

Metal-organic frameworks (MOFs) are recognized as ideal candidates for many applications such as gas sorption and catalysis. For a long time the properties of these materials were thought to essentially arise from their well-defined crystal structures. It is only recently that the importance of structural defects for the properties of MOFs has been evidenced. In this work, salt-assisted and liquid-assisted grinding were used to introduce defects in a copper-based MOF, namely HKUST-1. Different milling times and post-synthetic treatments with alcohols allow introduction of defects in the form of free carboxylic acid groups or reduced copper(i) sites. The nature and the amount of defects were evaluated by spectroscopic methods (FTIR, XPS) as well as TGA and NH3temperature-programmed desorption experiments. The negative impact of free -COOH groups on the catalytic cyclopropanation reaction of ethyl diazoacetate with styrene, as well as on the gravimetric CO2sorption capacities of the materials, was demonstrated. The improvement of the catalytic activity of carboxylic acid containing materials by the presence of CuIsites was also evidenced.

Carbenoid transfer in competing reactions catalyzed by ruthenium complexes

Dragutan, Ileana,Dragutan, Valerian,Verpoort, Francis

, p. 211 - 215 (2014)

Aiming at improving catalyst activity, ten ruthenium promoters have been investigated in carbenoid transfer from ethyl diazoacetate to styrene as a model substrate. Optimal selectivity in cyclopropanation has been attained with the new NHC-Ru complex 10, as well as with the Fischer carbene 7. The surprising non-metathetical behavior of the Grubbs' first-generation catalyst in this multifaceted process is highlighted. Copyright

-

Armstrong,R.K.

, p. 618 - 620 (1966)

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Catalytic transformations of diazo compounds promoted by platinum(0) and dicationic platinum(II) complexes

Bertani, Roberta,Biasiolo, Monica,Darini, Katia,Michelin, Rino A,Mozzon, Mirto,Visentin, Fabiano,Zanotto, Livio

, p. 32 - 39 (2002)

9-Diazofluorene (DAF) is decomposed either stoichiometrically or catalytically in the presence of the platinum(0) complex [Pt(C2H4)(PPh3)2] to give difluoren-9-ylidene-hydrazine in high yield. Under analogous reaction conditions, diphenyldiazomethane gives mostly the azine, Ph2CNNCPh2, while ethyl diazoacetate (EDA) affords, in low yield, a mixture of diethyl fumarate and maleate in approximately 10:1 molar ratio. The cyclopropanation of styrene with EDA is catalyzed by a series of dicationic complexes of the type [PtL2(NCCH3)2][Y]2 (L2=2PPh3, Ph2PCH=CHPPh2, Ph2PCH2CH2PPh2; Y=BF4, CF3SO3) in 1,2-dichloroethane at 60 °C for 24 h. DAF and EDA undergo insertion reactions into the OH bond of alcohols ROH (R=Me, Et, t-Bu, CH2CHCH2, Ph) at 25 °C in CH2Cl2-ROH (DAF or EDA-ROH molar ratio 1/20) in the presence of 1% mol of several dicationic platinum(II) complexes to give the corresponding ethers in excellent yields.

-

Nakamura et al.

, p. 593 (1978)

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Continuous flow asymmetric cyclopropanation reactions using Cu(i) complexes of Pc-L* ligands supported on silica as catalysts with carbon dioxide as a carrier

Castano, Brunilde,Gallo, Emma,Cole-Hamilton, David J.,Dal Santo, Vladimiro,Psaro, Rinaldo,Caselli, Alessandro

, p. 3202 - 3209 (2014)

Continuous flow heterogeneous asymmetric cyclopropanations catalysed by supported hydrogen-bonded (SHB) chiral copper(i) complexes of pyridine containing tetraazamacrocyclic ligands Pc-L* using CO2 as a transport vector are described. The catalytic system showed high stability and good recyclability without loss of activity for at least 24 h in CO2 and catalyst turnover numbers up to 440 were obtained with excellent conversion (up to 99%) and high selectivity (up to 88%). No leaching of copper was observed. Cyclopropane products from both aromatic and aliphatic olefins were obtained in good yields with enantiomeric excesses up to 72%. This journal is the Partner Organisations 2014.

Cobalt carbaporphyrin-catalyzed cyclopropanation

Fields, Kimberly B.,Engle, James T.,Sripothongnak, Saovalak,Kim, Chungsik,Zhang, X. Peter,Ziegler, Christopher J.

, p. 749 - 751 (2011)

Cobalt complexes of N-confused porphyrins and benziphthalocyanine, which both feature organometallic bonds at the macrocycle cores, catalyze the cyclopropanation of styrene with a higher trans-selectivity than the corresponding porphyrin and phthalocyanine complexes. The Royal Society of Chemistry 2011.

Hydrogenation of Alkynes with Water and a Titanium(II) Complex

Demerseman, Bernard,Dixneuf, Pierre H.

, p. 665 - 666 (1981)

μ-Oxobis(dicyclopentadienyl)(alkenyl)titanium(IV) complexes were prepared from (η5-C5H5)2Ti(CO)2 and alkyne in the presence of water and gave the corresponding cis-olefins.

Iron porphyrins catalyze the synthesis of non-protected amino acid esters from ammonia and diazoacetates

Aviv, Iris,Gross, Zeev

, p. 4477 - 4479 (2006)

Iron complexes of porphyrins (and corroles to a lesser extent) are the first catalysts to utilize ammonia for the synthesis of N-free amino acid esters. The Royal Society of Chemistry 2006.

Rhodium-mediated stereoselective polymerization of "carbenes"

Hetterscheid, Dennis G. H.,Hendriksen, Coen,Dzik, Wojciech I.,Smits, Jan M. M.,Van Eck, Ernst R. H.,Rowan, Alan E.,Busico, Vincenzo,Vacatello, Michele,Van Axel Castelli, Valeria,Segre, Annalaura,Jellema, Erica,Bloemberg, Tom G.,De Bruin, Bas

, p. 9746 - 9752 (2006)

Unprecedented rhodium-catalyzed stereoselective polymerization of "carbenes" from ethyl diazoacetate (EDA) to give high molecular mass poly(ethyl 2-ylidene-acetate) is described. The mononuclear, neutral [(N,O-ligand)M1(cod)] (M = Rh, Ir) catalytic precursors for this reaction are characterized by (among others) single-crystal X-ray diffraction. These species mediate formation of a new type of polymers from EDA: carbon-chain polymers functionalized with a polar substituent at each carbon of the polymer backbone. The polymers are obtained as white powders with surprisingly sharp NMR resonances. Solution and solid state NMR data for these new polymers reveal a highly stereoregular polymer, with a high degree of crystallinity. The polymer is likely syndiotactic. Material properties are very different from those of atactic poly(diethyl fumarate) polymer obtained by radical polymerization of diethyl fumarate. Other diazoacetates are also polymerized. Further studies are underway to reveal possible applications of these new materials.

-

Klostergaard

, p. 108 (1958)

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Monomeric Rhodium(II) Catalysts for the Preparation of Aziridines and Enantioselective Formation of Cyclopropanes from Ethyl Diazoacetate at Room Temperature

Krumper,Gerisch,Suh,Bergman,Tilley

, p. 9705 - 9710 (2003)

A family of bis(oxazoline) complexes of coordinatively unsaturated monomeric rhodium (II) (2a,b,3a,b) are described. These complexes serve as catalysts for cyclopropanation of olefins by ethyl diazoacetate, giving excellent yields (66-84%). The reaction shows an unusual preference for formation of the cis isomers. Catalytic aziridination of N-aryl imines with diazoacetate is also described.

Highly enantioselective ruthenium/PNNP-catalyzed imine aziridination: Evidence of carbene transfer from a diazoester complex

Egloff, Joel,Ranocchiari, Marco,Schira, Amata,Schotes, Christoph,Mezzetti, Antonio

, p. 4690 - 4701 (2013)

The ruthenium/PNNP complexes [RuCl(Et2O)(PNNP)]Y (Y = PF 6, 4PF6; BF4, 4BF4; or SbF 6, 4SbF6) (10 mol %) catalyze the enantioselective aziridination of imines with ethyl diazoacetate (EDA) as carbene source (PNNP = (1S,2S)-N,N′-bis[o-(diphenylphosphino)benzylidene]cyclohexane-1,2-diamine) . The highest enantioselectivity was obtained with 4SbF6, which aziridinated N-benzylidene-1,1-diphenylmethanamine (5a) to cis-ethyl 1-benzhydryl-3-phenylaziridine-2-carboxylate (cis-6a) with 93% ee at 0 C. To the best of our knowledge, this is the highest enantioselectivity ever obtained in transition metal-catalyzed asymmetric aziridination. Aziridine yields were overall moderate to low (up to 33% isolated yield of the cis isomer) because of the competitive formation of diethyl maleate (7). The scope of the catalyst was studied with p- and m-substituted imines. NMR spectroscopic studies with 13C- and 15N-labeled EDA indicate that aziridine 6a is formed by carbene transfer from an EDA complex, [RuCl(EDA)(PNNP)]PF6 (8), to the imine. The observation of a dinitrogen complex (9) gives further support to this mechanism. The EDA adduct 8 decomposes to the carbene complex [RuCl(CHCO2Et)(PNNP)]+ (10), whose reaction with EDA gives diethyl maleate. This unprecedented mechanism is rationalized on the basis of the nucleophilic nature of diazoalkanes, which is enhanced by coordination to a π-back-donating metal such as ruthenium(II).

Dominant Disrotatory Double Rotation in the Thermally Induced 1,2-Dimethylspiropentane Geometric Isomerization

Gajewski, Joseph J.,Chang, Ming Jing

, p. 7542 - 7545 (1980)

Pyrolysis of optically active trans-1,2-dimethylspiropentane and syn-4,4-dideuterio-cis-1,2-dimethylspiropentane at 290.0 deg C in the vapor-phase allowed determination of kT->C + kC->T = 3.43E-5 /s, Keq(T/C) = 2.41, kTact->Trac = 1.36E-5 /s, and kCS->CS+CA = 8.76E-5 /s.This data indicates preferred double over single rotation in the cleavage of the C-1, C-2 bond, particularly with the cis isomer.The greater preference for double inversion over single inversion from the cis relative to the trans isomer suggests that the double inversion occurs by a disrotatory pathway.Pyrolysis of optically active trans,medial- and trans,proximal-1,2,4-trimethylspiropentanes at low conversions revealed that the previously observed interconversions of these isomers occur predominantly by C-4, C-5 bond cleavage and not by double rotation after C-1, C-2 bond fission.These observations reinforce the conclusion above that the dominant pathway for double rotation in spiropentane isomers is disrotatory.

Iridium-catalyzed aziridination of aliphatic aldehydes, aliphatic amines and ethyl diazoacetate

Kubo, Takashi,Sakaguchi, Satoshi,Ishii, Yasutaka

, p. 625 - 626 (2000)

Three-component coupling reactions of aliphatic aldehydes, aliphatic amines and ethyl diazoacetate to the corresponding aziridine derivatives has been achieved by the use of [Ir(cod)Cl]2 as a catalyst under mild conditions; for instance, the reaction of n-butyraldehyde, tert-butylamine and ethyl diazoacetate in the presence of a catalytic amount of [Ir(cod)Cl]2 in THF at -10 °C gave 1-tert-butyl-2-ethoxycarbonyl-3-propylaziridine in 85% yield in high stereoselectivity (cis: trans = 96:4).

Stable N-heterocyclic carbene (NHC)-palladium(0) complexes as active catalysts for olefin cyclopropanation reactions with ethyl diazoacetate

Martin, Carmen,Molina, Francisco,Alvarez, Eleuterio,Belderrain, Tomas R.

, p. 14885 - 14895 (2011)

The Pd0 complexes [(NHC)PdLn] (NHC=N-heterocyclic carbene ligand; L=styrene for n=2 or PR3 for n=1) efficiently catalyse olefin cyclopropanation by using ethyl diazoacetate (EDA) as the carbene source with activities that improve on previously described catalytic systems based on this metal. Mechanistic studies have shown that all of these catalyst precursors deliver the same catalytic species in solution, that is, [(IPr)Pd(sty)], a 14e- unsaturated intermediate that further reacts with EDA to afford [(IPr)Pd(=CHCO2Et)(sty)], from which the cyclopropane is formed.

A family of highly active copper(I)-homoscorpionate catalysts for the alkyne cyclopropenation reaction

Diaz-Requejo,Mairena,Belderrain,Nicasio,Trofimenko,Perez

, p. 1804 - 1805 (2001)

Equimolar mixtures of ethyl diazoacetate and alkynes can be converted into cyclopropenes in very high yields, at room temperature, through the intermediacy of readily available Cu(I) catalysts containing trispyrazolylborate ligands.

The role of the support properties in the catalytic performance of an anchored copper(ii) aza-bis(oxazoline) in mesoporous silicas and their carbon replicas

Silva, Ana Rosa,Guimaraes, Vanessa,Carvalho, Ana Paula,Pires, Joao

, p. 659 - 672 (2013)

A copper(ii) chiral aza-bis(oxazoline) catalyst (CuazaBox) was anchored onto ordered mesoporous silicas and their carbon replicas. The materials were characterized by elemental analysis (C, N, H, S), ICP-AES, FTIR, XPS, thermogravimetry and isotherms of N2 adsorption at -196 °C. The materials were tested as heterogeneous catalysts in the reaction of cyclopropanation of styrene to check the effect of porous material type on the catalytic parameters, as well as on their reutilization. Generally, the composites were more active and enantioselective in the cyclopropanation of styrene than the corresponding homogeneous phase reaction run under similar experimental conditions. The materials pHpzc proved to be an important factor not only in the CuazaBox anchoring yields, but also in their catalytic performance. Less acidic surfaces (SPSi and CMK-3) yielded heterogeneous catalysts with higher styrene conversion and enantioselectivity. The materials could also be recycled with comparable enantioselectivities or generally a slight decrease in the enantioselectivity.

Metal-organic framework based on copper(I) sulfate and 4,4′- bipyridine catalyzes the cyclopropanation of styrene

Shi, Fa-Nian,Silva, Ana Rosa,Rocha, Joao

, p. 2196 - 2203 (2011)

The hydrothermal synthesis of a new metal-organic framework (MOF) formulated as Cu2(4,4′-bpy)2SO4· 6(H2O), [abbreviation: (1); bpy or 4,4′-bpy=4,4′- bipyridine; SO42-=sulfate group] has been reported. The structure of this MOF consists of Cu+ nodes connected via 4,4′-bpy to form infinite chains, with two neighboring chains further bridged on the nodes by SO42-, resulting in a 1-D double chain network. Guest water molecules reside in between the chains and are hydrogen-bonded to the O and S atoms from the nearest sulfate groups, leading to the formation of a 3-D supramolecular framework. This MOF is good heterogeneous catalyst for the cyclopropanation of styrene, with high trans cyclopropane diastereoselectivity and was recycled and reused for three consecutive cycles without a significant loss of catalytic activity.

Crystal structures of sodium dimethyl sulfosuccinate and sodium diethyl sulfosuccinate

Nagasoe, Yasuyuki,Hattori, Norikatsu,Masuda, Hideki,Okabayashi, Hirofumi,O'Connor, Charmian J.

, p. 61 - 68 (1998)

The crystal structures of sodium dimethyl sulfosuccinate and sodium diethyl sulfosuccinate have been determined by the single crystal X-ray diffraction method. Sodium dimethyl sulfosuccinate (SDMS, C6H9O7SNa·H2O, Mr = 266.20) crystallizes in a triclinic space group P1 with unit cell dimensions a = 5.5971 (8), b = 6.5388 (5), c = 15.267 (2) A, α = 77.855 (8), β = 85.90 (1), γ = 84.95 (1)°. The crystal of sodium diethyl sulfosuccinate (SDES, C8H13O7SNa·3H2O, Mr = 330.29) has a monoclinic space group C2/c with unit cell dimensions a = 34.754 (3), b = 6.0322 (7), c = 15.0777 (9) A, β = 104.385 (7)°. In the SDMS and SDES crystals, the Na+ ion, which is coordinated to six oxygen atoms, forms an octahedral structure. For SDMS, the Na+ ion is coordinated to four oxygen atoms of SO3/- groups and to the two oxygen atoms of water molecules of hydration. For SDES, the Na+ ion is coordinated to the oxygen atom of the β-chain C=O group, one of the SO3/- oxygen atoms and four oxygen atoms of hydrating water molecules. It was found that splitting of the C=O stretch band caused by the Na...O=C coordination occurs in the IR and Raman spectra of SDES.

Rh-mediated polymerization of carbenes: Mechanism and stereoregulation

Jellema, Erica,Budzelaar, Peter H. M.,Reek, Joost N. H.,De Bruin, Bas

, p. 11631 - 11641 (2007)

Ligand variation, kinetic investigations, and computational studies have been used to elucidate the mechanism of rhodium-catalyzed diazoalkane polymerization. Variations in the "N,O" donor part of the catalyst precursors (diene)RhI(N,O) result in different activities but virtually identical molecular weights, indicating that this part of the precursor is lost on forming the active species. In contrast, variation of the diene has a major effect on the nature of the polymer produced, indicating that the diene remains bound during polymerization. Kinetic studies indicate that only a small fraction of the Rh (1-5%) is involved in polymerization catalysis; the linear relation between polymer yield and Mw suggests that the chains terminate slowly and chain transfer is not observed (near living character). Oligomers and fumarate/maleate byproducts are most likely formed from other "active" species. Calculations support a chain propagation mechanism involving diazoalkane coordination at the carbon atom, N2 elimination to form a carbene complex, and carbene migratory insertion into the growing alkyl chain. N2 elimination is calculated to be the rate-limiting step. On the basis of a comparison of NMR data with those of known oligomer fragments, the stereochemistry of the new polymer is tentatively assigned as syndiotactic. The observed syndiospecificity is attributed to chain-end control on the rate of N2 elimination from diastereomeric diazoalkane complexes and/or on the migratory insertion step itself.

New N-methylimidazolium hexachloroantimonate: Synthesis, crystal structure, Hirshfeld surface and catalytic activity of in cyclopropanation of stryrene

Boschini, Frédéric,Mahmoud, Abdelfattah,Sénam Etsè, Koffi,Zaragoza, Guillermo

, (2020)

The N-methylimidazolium hexachloroantimonate salt Cl6Sb·C4H7N2 (MIMSb), was prepared and fully characterized. In 1H NMR spectrum, the N-H proton shifted to downfield because of the presence of SbCl6? and appears as a triplet at 13.19 ppm. Characterization with IR spectroscopy shows strong absorption band at around 699 cm?1 which is attributed to Sb?Cl stretching. Furthermore, UV–visible analysis at high concentrations in DMSO suggested that MIMSb interacts with DMSO leading to an absorption in visible region at λmax of 426 nm. Electrochemical characterization using cyclic voltammetry demonstrates three redox processes with reduction peaks at 0.69, ?0.13 and ?0.50 V. Finally, molecular structure of the product was determined by X-ray diffraction analysis. The crystal structure determination was carried out with Mo-Kα X-ray and data measured at 100 K. The title compound crystallizes in monoclinic P21/c space group with unit cell parameters a = 7.1131 (5) ?, b = 12.4436 (9) ?, c = 14.1658 (11) ?, V = 1241.86 (16) ?3 and Z = 4. The crystal packing is stabilized by H—Cl interaction. The analysis of intermolecular interactions was realized through the mapping of contact descriptors dnorm, shape-index and the fingerprint reveling that the most significant contribution to the Hirshfeld surface (69.4%) is from H—Cl contacts. Finally, the catalytic activity of MIMSb was probed in the cyclopropanation of styrene with ethyl diazoacetate.

Synthesis, structure and reactivity of iridium complexes containing a bis-cyclometalated tridentate C^N^C ligand

Cheng, Shun-Cheung,Cheung, Wai-Man,Chong, Man-Chun,Ko, Chi-Chiu,Leung, Wa-Hung,Sung, Herman H.-Y.,Williams, Ian D.

, p. 8512 - 8523 (2021)

In an effort to synthesize cyclometalated iridium complexes containing a tridentate C^N^C ligand, transmetallation of [Hg(HC^N^C)Cl] (1) (H2C^N^C = 2,6-bis(4-tert-butylphenyl)pyridine) with various organoiridium starting materials has been studied. The treatment of1with [Ir(cod)Cl]2(cod = 1,5-cyclooctadiene) in acetonitrile at room temperature afforded a hexanuclear Ir4Hg2complex, [Cl(κ2C,N-HC^N^C)(cod)IrHgIr(cod)Cl2]2(2), which features Ir-Hg-Ir and Ir-Cl-Ir bridges. Refluxing2with sodium acetate in tetrahydrofuran (thf) resulted in cyclometalation of the bidentate HC^N^C ligand and formation of trinuclear [(C^N^C)(cod)IrHgIr(cod)Cl2] (3). On the other hand, refluxing [Ir(cod)Cl]2with1and sodium acetate in thf yielded [Ir(C^N^C)(cod)(HgCl)] (4). Chlorination of4with PhICl2gave [Ir(C^N^C)(cod)Cl]·HgCl2(5·HgCl2) that reacted with tricyclohexylphosphine to yield Hg-free [Ir(C^N^C)(cod)Cl] (5). Chloride abstraction of5with silver(i) triflate (AgOTf) gave [Ir(C^N^C)(cod)(H2O)](OTf) (6) that can catalyze the cyclopropanation of styrene with ethyl diazoacetate. Reaction of1and [Ir(CO)2Cl(py)] (py = pyridine) with sodium acetate in refluxing thf afforded [Ir(C^N^C)(HgCl)(py)(CO)] (7), in which the carbonyl ligand is coplanar with the C^N^C ligand. On the other hand, refluxing1with (PPh4)[Ir(CO)2Cl2] and sodium acetate in acetonitrile gave [Ir(C^N^C)(κ2C,N-HC^N^C)(CO)] (8), the carbonyl ligand of which istransto the pyridyl ring of the bidentate HC^N^C ligand. Upon irradiation with UV light8in thf was isomerized to8′, in which the carbonyl istransto a phenyl group of the bidentate HC^N^C ligand. The isomer pair8and8′exhibited emission at 548 and 514 nm in EtOH/MeOH at 77 K with lifetime of 84.0 and 64.6 μs, respectively. Protonation of8withp-toluenesulfonic acid (TsOH) afforded the bis(bidentate) tosylate complex [Ir(κ2C,N-HC^N^C)2(CO)(OTs)] (9) that could be reconverted to8upon treatment with sodium acetate. The electrochemistry of the Ir(C^N^C) complexes has been studied using cyclic voltammetry. Reaction of [Ir(PPh3)3Cl] with1and sodium acetate in refluxing thf led to isolation of the previously reported compound [Ir(κ2P,C-C6H4PPh2)2(PPh3)Cl] (10). The crystal structures of2-5,8,8′,9and10have been determined.

Highly stereoselective formation of cis-enediones from α-diazo carbonyl compounds catalysed by [RuCl(η5-C5H5)PPh32]

Baratta, Walter,Del Zotto, Alessandro,Rigo, Pierluigi

, p. 2163 - 2164 (1997)

Stereoselective decomposition of the α-diazo carbonyl compounds N2CHCOR [R = Me, Prn, Pri, (CH2)10CH3] catalysed by [RuCl(η5-C5H5)(PPh3) 2] (0.1 mol%) in toluene at 65°C affords quantitatively RCOCH=CHCOR carbene dimers, the cis isomers being formed in 95-97% yield; under the same experimental conditions N2CHCOEt gives diethyl maleate in a purity of greater than 99%, the highest value for a stereoselective carbene-carbene dimer formation reported to date.

The effect of catalyst loading in copper-catalyzed cyclohexane functionalization by carbene insertion

Caballero, Ana,Diaz-Requejo, M. Mar,Trofimenko, Swiatoslaw,Belderrain, Tomas R.,Perez, Pedro J.

, p. 2848 - 2852 (2007)

A study of the variables that affect the insertion of the :CHCO 2Et group (formed from ethyl diazocetate, EDA) into the C-H bonds of cyclohexane in the presence of a TpxCu complex as the catalyst (Tpx = trispyrazolylborate ligand) has demonstrated an anomalous effect of the catalyst loading. The use of low concentrations of catalyst produces an increase in the yield of the C-H activation product ethyl cyclohexaneacetate. This effect has also been found in the case of other less elaborated catalysts such as [BpBr3Cu] or [(bipy)2-Cu][I]. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

One-pot production of diethyl maleate via catalytic conversion of raw lignocellulosic biomass

Cai, Zhenping,Chen, Rujia,Zhang, Hao,Li, Fukun,Long, Jinxing,Jiang, Lilong,Li, Xuehui

supporting information, p. 10116 - 10122 (2021/12/24)

The conversion of lignocellulose into a value-added chemical with high selectivity is of great significance but is a big challenge due to the structural diversities of biomass components. Here, we have reported an efficient approach for the one-step conversion of raw lignocellulose into diethyl maleate by the polyoxometalate ionic liquid [BSmim]CuPW12O40 in ethanol under mild conditions. The results reveal that all of the fractions in biomass, i.e., cellulose, lignin and hemicellulose, were simultaneously converted into diethyl maleate (DEM), achieving a 329.6 mg g-1 yield and 70.3% selectivity from corn stalk. Importantly, the performance of the ionic liquid catalyst [BSmim]CuPW12O40 was nearly twice that of CuHPW12O40, which can be attributed to the lower incorporation of the Cu2+ site in [BSmim]CuPW12O40. Hence, this process opens a promising route for producing bio-based bulk chemicals from raw lignocellulose without any pretreatment.

Practical and Regioselective Synthesis of C-4-Alkylated Pyridines

Baran, Phil S.,Choi, Jin,Godineau, Edouard,Laudadio, Gabriele

supporting information, p. 11927 - 11933 (2021/08/20)

The direct position-selective C-4 alkylation of pyridines has been a long-standing challenge in heterocyclic chemistry, particularly from pyridine itself. Historically this has been addressed using prefunctionalized materials to avoid overalkylation and mixtures of regioisomers. This study reports the invention of a simple maleate-derived blocking group for pyridines that enables exquisite control for Minisci-type decarboxylative alkylation at C-4 that allows for inexpensive access to these valuable building blocks. The method is employed on a variety of different pyridines and carboxylic acid alkyl donors, is operationally simple and scalable, and is applied to access known structures in a rapid and inexpensive fashion. Finally, this work points to an interesting strategic departure for the use of Minisci chemistry at the earliest possible stage (native pyridine) rather than current dogma that almost exclusively employs Minisci chemistry as a late-stage functionalization technique.

Comparative Study of the Electronic Structures of μ-Oxo, μ-Nitrido, and μ-Carbido Diiron Octapropylporphyrazine Complexes and Their Catalytic Activity in Cyclopropanation of Olefins

Cailler, Lucie P.,Clémancey, Martin,Barilone, Jessica,Maldivi, Pascale,Latour, Jean-Marc,Sorokin, Alexander B.

, p. 1104 - 1116 (2020/02/04)

The electronic structure of three single-Atom bridged diiron octapropylporphyrazine complexes (FePzPr8)2X having Fe(III)-O-Fe(III), Fe(III)-N-Fe(IV) and Fe(IV)-C-Fe(IV) structural units was investigated by M?ssbauer spectroscopy and density functional theory (DFT) calculations. In this series, the isomer shift values decrease, whereas the values of quadrupole splitting become progressively greater indicating the increase of covalency of Fe-X bond in the μ-oxo, μ-nitrido, μ-carbido row. The M?ssbauer data point to low-spin systems for the three complexes, and calculated data with B3LYP-D3 show a singlet state for μ-oxo and μ-carbido and a doublet state for μ-nitrido complexes. An excellent agreement was obtained between B3LYP-D3 optimized geometries and X-ray structural data. Among (FePzPr8)2X complexes, μ-oxo diiron species showed a higher reactivity in the cyclopropanation of styrene by ethyl diazoacetate to afford a 95% product yield with 0.1 mol % catalyst loading. A detailed DFT study allowed to get insight into electronic structure of binuclear carbene species and to confirm their involvement into carbene transfer reactions.

Method for preparing maleate by catalyzing maleic anhydride with ionic liquid

-

Paragraph 0037; 0040; 0041; 0044, (2020/02/29)

The invention discloses a method for preparing maleate by catalyzing maleic anhydride with ionic liquid. The preparation method is characterized by comprising the following steps: mixing ionic liquidwith maleic anhydride and fatty alcohol, carrying out heating to 80-140 DEG C, and performing a reaction for 0.5-4 h to obtain maleate, wherein the usage amount of the ionic liquid accounts for 0.1-10% by mol of the maleic anhydride, and a molar ratio of fatty alcohol to maleic anhydride is 2-12. A high-added-value chemical with the completely-esterified maleate as a main product is prepared in the invention. The method is simple in process, mild in conditions, friendly to environment and high in double esterification degree; and the ionic liquid is high in activity, not prone to inactivationand capable of being cyclically used.

Process route upstream and downstream products

Process route

styrenesulfide
1498-99-3

styrenesulfide

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

Diethyl maleate
141-05-9

Diethyl maleate

Conditions
Conditions Yield
In toluene; for 48h; Heating;
40 % Spectr.
70 % Spectr.
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

diazoacetone
2684-62-0

diazoacetone

(Z)-hex-3-ene-2,5-dione
17559-81-8

(Z)-hex-3-ene-2,5-dione

(Z)-ethyl 4-oxopent-2-enoate
200628-30-4

(Z)-ethyl 4-oxopent-2-enoate

Diethyl maleate
141-05-9

Diethyl maleate

Conditions
Conditions Yield
chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); In chloroform-d1; at 60 ℃;
58 % Spectr.
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

2-diazo-acetophenone
3282-32-4

2-diazo-acetophenone

(Z)-1,4-diphenylbut-2-ene-1,4-dione
959-27-3

(Z)-1,4-diphenylbut-2-ene-1,4-dione

ethyl (E)-4-oxo-4-phenyl-2-butenoate
15121-89-8

ethyl (E)-4-oxo-4-phenyl-2-butenoate

(Z)-ethyl 4-oxo-4-phenylbut-2-enoate
20908-27-4

(Z)-ethyl 4-oxo-4-phenylbut-2-enoate

1,4-diphenylbut-2-ene-1,4-dione
959-28-4

1,4-diphenylbut-2-ene-1,4-dione

Diethyl maleate
141-05-9

Diethyl maleate

Conditions
Conditions Yield
With gold; In 1,2-dichloro-ethane; at 60 ℃; for 24h;
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

2,5-Dimethyl-2,4-hexadiene
764-13-6

2,5-Dimethyl-2,4-hexadiene

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

diethyl Fumarate
623-91-6

diethyl Fumarate

Diethyl maleate
141-05-9

Diethyl maleate

Conditions
Conditions Yield
hexarhodium hexadecacarbonyl; at 60 ℃; for 7h;
91%
ethanol
64-17-5

ethanol

ethyl 3-furancarboxylate
614-98-2

ethyl 3-furancarboxylate

ethyl 3,3-diethoxypropanoate
10601-80-6

ethyl 3,3-diethoxypropanoate

diethyl Fumarate
623-91-6

diethyl Fumarate

Diethyl maleate
141-05-9

Diethyl maleate

succinic acid diethyl ester
123-25-1

succinic acid diethyl ester

Conditions
Conditions Yield
With H(1+)*O40PW12(3-)*Cu(2+); oxygen; at 170 ℃; for 4h; under 7500.75 Torr; Autoclave;
ethanol
64-17-5

ethanol

ethyl 3-furancarboxylate
614-98-2

ethyl 3-furancarboxylate

diethyl Fumarate
623-91-6

diethyl Fumarate

Ethyl diethoxyacetate
6065-82-3

Ethyl diethoxyacetate

Diethyl maleate
141-05-9

Diethyl maleate

succinic acid diethyl ester
123-25-1

succinic acid diethyl ester

Conditions
Conditions Yield
With H(1+)*O40PW12(3-)*Cu(2+); oxygen; at 170 ℃; for 4h; under 7500.75 Torr; Autoclave;
ethanol
64-17-5

ethanol

D-glucose
50-99-7

D-glucose

ethyl 3-furancarboxylate
614-98-2

ethyl 3-furancarboxylate

malondialdehyde bis(diethyl acetal)
122-31-6

malondialdehyde bis(diethyl acetal)

ethyl 3,3-diethoxypropanoate
10601-80-6

ethyl 3,3-diethoxypropanoate

4-oxopentanoic acid ethyl ester
539-88-8

4-oxopentanoic acid ethyl ester

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

diethyl malonate
105-53-3

diethyl malonate

diethyl Fumarate
623-91-6

diethyl Fumarate

Ethyl diethoxyacetate
6065-82-3

Ethyl diethoxyacetate

Diethyl maleate
141-05-9

Diethyl maleate

succinic acid diethyl ester
123-25-1

succinic acid diethyl ester

Conditions
Conditions Yield
With oxygen; O40PW12(3-)*Cu(2+)*C8H15N2O3S(1+); at 170 ℃; for 4h; under 7500.75 Torr; Autoclave;
ethanol
64-17-5

ethanol

ethyl 3-furancarboxylate
614-98-2

ethyl 3-furancarboxylate

malondialdehyde bis(diethyl acetal)
122-31-6

malondialdehyde bis(diethyl acetal)

ethyl 3-ethoxypropionate
763-69-9

ethyl 3-ethoxypropionate

ethyl 3,3-diethoxypropanoate
10601-80-6

ethyl 3,3-diethoxypropanoate

4-oxopentanoic acid ethyl ester
539-88-8

4-oxopentanoic acid ethyl ester

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

diethyl malonate
105-53-3

diethyl malonate

diethyl Fumarate
623-91-6

diethyl Fumarate

Ethyl diethoxyacetate
6065-82-3

Ethyl diethoxyacetate

Diethyl maleate
141-05-9

Diethyl maleate

succinic acid diethyl ester
123-25-1

succinic acid diethyl ester

Conditions
Conditions Yield
With oxygen; O40PW12(3-)*Cu(2+)*C8H15N2O3S(1+); at 170 ℃; for 4h; under 7500.75 Torr; Autoclave;
(+/-)-6.7-dimethoxy-3ξ-methyl-1.2.3.4-tetrahydro-naphthalene-dicarboxylic acid-(1<i>r</i>.2<i>c</i>)-diethyl ester

(+/-)-6.7-dimethoxy-3ξ-methyl-1.2.3.4-tetrahydro-naphthalene-dicarboxylic acid-(1r.2c)-diethyl ester

Methylisoeugenol
93-16-3

Methylisoeugenol

Diethyl maleate
141-05-9

Diethyl maleate

Conditions
Conditions Yield
Erhitzen;
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

ethyl 2-cyclohexylacetate
5452-75-5

ethyl 2-cyclohexylacetate

Diethyl maleate
141-05-9

Diethyl maleate

Conditions
Conditions Yield
With rhodium(II) pivalate; Heating;
10%
67%

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