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Journal articles on the topic 'Metal carbonyl compounds'

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Published: 25 July 2024
Last updated: 31 July 2024

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1

Bond, Alan M., and Ray Colton. "Electrochemical studies of metal carbonyl compounds." Coordination Chemistry Reviews 166 (November 1997): 161–80. http://dx.doi.org/10.1016/s0010-8545(97)00022-2.

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2

Araki, Shuki, Hirokazu Ito, and Yasuo Batsugan. "Cadmium metal-mediated allylation of carbonyl compounds." Journal of Organometallic Chemistry 347, no. 1-2 (June 1988): 5–9. http://dx.doi.org/10.1016/0022-328x(88)80263-8.

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3

Lee, Ha-Eun, Dopil Kim, Ahrom You, Myung Hwan Park, Min Kim, and Cheoljae Kim. "Transition Metal-Catalyzed α-Position Carbon–Carbon Bond Formations of Carbonyl Derivatives." Catalysts 10, no. 8 (August 2, 2020): 861. http://dx.doi.org/10.3390/catal10080861.

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α-Functionalization of carbonyl compounds in organic synthesis has traditionally been accomplished via classical enolate chemistry. As α-functionalized carbonyl moieties are ubiquitous in biologically and pharmaceutically valuable molecules, catalytic α-alkylations have been extensively studied, yielding a plethora of practical and efficient methodologies. Moreover, stereoselective carbon–carbon bond formation at the α-position of achiral carbonyl compounds has been achieved by using various transition metal–chiral ligand complexes. This review describes recent advances—in the last 20 years and especially focusing on the last 10 years—in transition metal-catalyzed α-alkylations of carbonyl compounds, such as aldehydes, ketones, imines, esters, and amides and in efficient carbon–carbon bond formations. Active catalytic species and ligand design are discussed, and mechanistic insights are presented. In addition, recently developed photo-redox catalytic systems for α-alkylations are described as a versatile synthetic tool for the synthesis of chiral carbonyl-bearing molecules.
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4

Gibson, Dorothy H., and Yekhlef S. El-Omrani. "Selective reductions of carbonyl compounds with group 6 metal carbonyl hydrides." Organometallics 4, no. 8 (August 1985): 1473–75. http://dx.doi.org/10.1021/om00127a035.

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5

Jaitner, Peter, and Wolfgang Winder. "Reaction of α-Me2TeJ2 with metal carbonyl compounds." Inorganica Chimica Acta 134, no. 2 (November 1987): 201–2. http://dx.doi.org/10.1016/s0020-1693(00)88080-9.

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6

Aucott, Benjamin J., Anne-Kathrin Duhme-Klair, Benjamin E. Moulton, Ian P. Clark, Igor V. Sazanovich, Michael Towrie, L. Anders Hammarback, Ian J. S. Fairlamb, and Jason M. Lynam. "Manganese Carbonyl Compounds Reveal Ultrafast Metal–Solvent Interactions." Organometallics 38, no. 11 (May 23, 2019): 2391–401. http://dx.doi.org/10.1021/acs.organomet.9b00212.

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7

ALPER, H. "ChemInform Abstract: Metal-Catalyzed Routes to Carbonyl Compounds." ChemInform 26, no. 26 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199526303.

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8

BOND, A. M., and R. COLTON. "ChemInform Abstract: Electrochemical Studies of Metal Carbonyl Compounds." ChemInform 29, no. 17 (June 23, 2010): no. http://dx.doi.org/10.1002/chin.199817281.

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9

Nishino, Toshiki, Yutaka Nishiyama, and Noboru Sonoda. "Reductive coupling of carbonyl compounds using lanthanum metal." Heteroatom Chemistry 11, no. 1 (2000): 81–85. http://dx.doi.org/10.1002/(sici)1098-1071(2000)11:1<81::aid-hc12>3.0.co;2-1.

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10

Chen, Hong, Zi-Chao Tang, Rong-Bin Huang, and Lan-Sun Zheng. "Photodissociation Mass Spectrometry of Trinuclear Carbonyl Clusters M3(CO)12 (M = Fe, Ru, Os)." European Journal of Mass Spectrometry 6, no. 1 (February 2000): 19–22. http://dx.doi.org/10.1255/ejms.301.

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Photodissociation of trinuclear carbonyl cluster compounds of Fe, Ru and Os was studied by recording the mass spectra produced from laser ablation of the cluster compounds. Under the experimental conditions, dissociation of the cluster compounds is very extensive, but the dissociation pathway of the osmium cluster is different from those of the iron and ruthenium clusters. The iron and ruthenium clusters not only lost their carbonyl ligands, but their cluster cores were also fragmented. As the osmium cluster dissociated, it ejected three pairs of oxygen atoms, in sequence, before losing the carbonyl ligands, but the trinuclear osmium core did not fragment. This specific dissociation scheme of the osmium cluster reveals its special structural stability. Not only does it have stronger metal-metal bonds, but also a relatively stable coordination bond formed between osmium and carbonyl ligands. In addition, different distributions of positive and negative fragment ions were observed in the experiment. This difference is interpreted as the result of different stabilities of their electronic structures.
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11

Yang, Xue-Yan, Ruizhe Wang, Lu Wang, Jianjun Li, Shuai Mao, San-Qi Zhang, and Nanzheng Chen. "K2S2O8-promoted C–Se bond formation to construct α-phenylseleno carbonyl compounds and α,β-unsaturated carbonyl compounds." RSC Advances 10, no. 48 (2020): 28902–5. http://dx.doi.org/10.1039/d0ra05927g.

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K2S2O8-promoted C–Se bond formation from the cross-coupling of C(sp3)–H bond adjacent to carbonyl group with diphenyl diselenide under metal-free conditions.
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12

Cheng, Jie, Jianwei Shao, Yifei Ye, Yang Zhao, Chengjun Huang, Li Wang, and Mingxiao Li. "Microfluidic Preconcentration Chip with Self-Assembled Chemical Modified Surface for Trace Carbonyl Compounds Detection." Sensors 18, no. 12 (December 13, 2018): 4402. http://dx.doi.org/10.3390/s18124402.

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Carbonyl compounds in water sources are typical characteristic pollutants, which are important indicators in the health risk assessment of water quality. Commonly used analytical chemistry methods face issues such as complex operations, low sensitivity, and long analysis times. Here, we report a silicon microfluidic device based on click chemical surface modification that was engineered to achieve rapid, convenient and efficient capture of trace level carbonyl compounds in liquid solvent. The micro pillar arrays of the chip and microfluidic channels were designed under the basis of finite element (FEM) analysis and fabricated by the microelectromechanical systems (MEMS) technique. The surface of the micropillars was sputtered with precious metal silver and functionalized with the organic substance amino-oxy dodecane thiol (ADT) by self-assembly for capturing trace carbonyl compounds. The detection of ppb level fluorescent carbonyl compounds demonstrates that the strategy proposed in this work shows great potential for rapid water quality testing and for other samples with trace carbonyl compounds.
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13

Grau, Benedikt W., and Svetlana B. Tsogoeva. "Iron-Catalyzed Carbonyl–Alkyne and Carbonyl–Olefin Metathesis Reactions." Catalysts 10, no. 9 (September 21, 2020): 1092. http://dx.doi.org/10.3390/catal10091092.

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Construction of carbon–carbon bonds is one of the most important tools for the synthesis of complex organic molecules. Among multiple possibilities are the carbonyl–alkyne and carbonyl–olefin metathesis reactions, which are used to form new carbon–carbon bonds between carbonyl derivatives and unsaturated organic compounds. As many different approaches have already been established and offer reliable access to C=C bond formation via carbonyl–alkyne and carbonyl–olefin metathesis, focus is now shifting towards cost efficiency, sustainability and environmentally friendly metal catalysts. Iron, which is earth-abundant and considered as an eco-friendly and inexpensive option in comparison to traditional metal catalysts, fulfils these requirements. Hence, the focus of this review is on recent advances in the iron-catalyzed carbonyl–alkyne, carbonyl–olefin and related C–O/C–O metathesis reactions. The still large research potential for ecologically and economically attractive and sustainable iron-based catalysts is demonstrated.
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14

Gong, Liu-Zhu, Pu-Sheng Wang, and Meng-Lan Shen. "Transition-Metal-Catalyzed Asymmetric Allylation of Carbonyl Compounds with Unsaturated Hydrocarbons." Synthesis 50, no. 05 (December 21, 2017): 956–67. http://dx.doi.org/10.1055/s-0036-1590986.

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The asymmetric allylation of carbonyl compounds is an important process for the formation of carbon–carbon bonds, generating optically active homoallylic alcohols that are versatile building blocks with widespread applications in organic synthesis. The use of readily available unsaturated hydrocarbons as allylating reagents in the transition-metal-catalyzed asymmetric allylation has received increasing interest as either a step- or an atom-economy alternative. This review summarizes transition-metal-catalyzed enantioselective allylations on the basis of the ‘indirect’ and ‘direct’ use of simple unsaturated hydrocarbons (include dienes, allenes, alkynes, and alkenes) as allylating reagents, with emphasis on highlighting conceptually novel reactions.1 Introduction2 ‘Indirect’ Use of Unsaturated Hydrocarbons in Asymmetric Allylation of Carbonyl Compounds2.1 Enantioselective Allylation with 1,3-Dienes2.2 Enantioselective Allylation with Allenes2.3 Enantioselective Allylation with Alkenes3 ‘Direct’ Use of Unsaturated Hydrocarbons in Asymmetric Allylation of Carbonyl Compounds3.1 Enantioselective Allylation with 1,3-Dienes3.2 Enantioselective Allylation with Allenes3.3 Enantioselective Allylation with Alkynes3.4 Enantioselective Allylation with Alkenes4 Conclusions
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15

Chen, Dao-Qian, Chun-Huan Guo, Heng-Rui Zhang, Dong-Po Jin, Xue-Song Li, Pin Gao, Xin-Xing Wu, Xue-Yuan Liu, and Yong-Min Liang. "A metal-free transformation of alkynes to carbonyls directed by remote OH group." Green Chemistry 18, no. 15 (2016): 4176–80. http://dx.doi.org/10.1039/c6gc01141a.

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16

Tang, Minhao, Fengtao Zhang, Yanfei Zhao, Yuepeng Wang, Zhengang Ke, Ruipeng Li, Wei Zeng, Buxing Han, and Zhimin Liu. "A CO2-mediated base catalysis approach for the hydration of triple bonds in ionic liquids." Green Chemistry 23, no. 24 (2021): 9870–75. http://dx.doi.org/10.1039/d1gc03865f.

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17

Law, Man Chun, Kwok-Yin Wong, and Tak Hang Chan. "Metal mediated allylation of carbonyl compounds in ionic liquids." Green Chemistry 4, no. 2 (March 25, 2002): 161–64. http://dx.doi.org/10.1039/b200924b.

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18

Cooke, Manning P., and Ioannis N. Houpis. "Metal-halogen exchange-initiated cyclization of iodo carbonyl compounds." Tetrahedron Letters 26, no. 41 (January 1985): 4987–90. http://dx.doi.org/10.1016/s0040-4039(01)80833-9.

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19

Smith, Alexander M. R., and King Kuok (Mimi) Hii. "Transition Metal Catalyzed Enantioselective α-Heterofunctionalization of Carbonyl Compounds." Chemical Reviews 111, no. 3 (March 9, 2011): 1637–56. http://dx.doi.org/10.1021/cr100197z.

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20

Azhdari Tehrani, Alireza, Hamed Abbasi, Leili Esrafili, and Ali Morsali. "Urea-containing metal-organic frameworks for carbonyl compounds sensing." Sensors and Actuators B: Chemical 256 (March 2018): 706–10. http://dx.doi.org/10.1016/j.snb.2017.09.211.

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21

Chaudhari, Moreshwar B., Yogesh Sutar, Shreyas Malpathak, Anirban Hazra, and Boopathy Gnanaprakasam. "Transition-Metal-Free C–H Hydroxylation of Carbonyl Compounds." Organic Letters 19, no. 13 (June 26, 2017): 3628–31. http://dx.doi.org/10.1021/acs.orglett.7b01616.

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22

Shimada, Masayuki, Yasushi Morimoto, and Shigetoshi Takahashi. "Preparation and properties of cyclodextrin-metal carbonyl inclusion compounds." Journal of Organometallic Chemistry 443, no. 1 (January 1993): C8—C10. http://dx.doi.org/10.1016/0022-328x(93)80024-6.

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23

Dantas, Juliana A., José Tiago M. Correia, Marcio W. Paixão, and Arlene G. Corrêa. "Photochemistry of Carbonyl Compounds: Application in Metal‐Free Reactions." ChemPhotoChem 3, no. 7 (April 16, 2019): 506–20. http://dx.doi.org/10.1002/cptc.201900044.

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24

Barik, Subrat Kumar, Dipak Kumar Roy, and Sundargopal Ghosh. "Chemistry of group 9 dimetallaborane analogues of octaborane(12)." Dalton Transactions 44, no. 2 (2015): 669–76. http://dx.doi.org/10.1039/c4dt03027c.

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25

Krishnankutty, K., Basheer Ummathur, and Perumpalli Ummer. "1-naphthylazo derivatives of some 1,3-dicarbonyl compounds and their Cu (II), Ni(II) and Zn(II) complexes." Journal of the Serbian Chemical Society 74, no. 11 (2009): 1273–82. http://dx.doi.org/10.2298/jsc0911273k.

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The coupling of diazotized 1-aminonaphthalene with 1,3-dicarbonyl compounds (acetylacetone, methylacetoacetate and acetoacetanilide) yielded a new series of bidentate ligand systems (HL). Analytical, IR, 1H-NMR and mass spectral data indicate that the compounds exist in the intramolecularly hydrogen bonded keto-hydrazone form. With Ni(II), Cu(II) and Zn(II), these potential monobasic bidentate ligands formed [ML2] type complexes. The IR, 1H- -NMR and mass spectral data of the complexes are consistent with the replacement of the chelated hydrazone proton of the ligand by a metal ion, thus leading to a stable six-membered chelate ring involving the hydrazone nitrogen and the hydrogen bonded carbonyl oxygen. The Ni(II) and Zn(II) chelates are diamagnetic, while the Cu(II) complexes are paramagnetic. In the metal complexes of the naphthylazo derivatives of acetylacetone and methylacetoacetate, the acetyl carbonyl is involved in coordination, whereas in the chelates of the naphthylazo derivative of acetoacetanilide, the anilide carbonyl is bonded with the metal ion.
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26

Chung, Seung-Won, Jaejung Ko, Kwonil Park, Sungil Cho, and Sang Ook Kang. "N,S-Chelating Amino-ortho-carboranethiolate Complexes of Rhodium and Iridium: Synthesis and Reactivity. X-Ray Crystal Structures of (η4-C8H12)Rh[(NMe2CH2)SC2B10H10] and (CO)2Rh[(NMe2CH2)SC2B10H10]." Collection of Czechoslovak Chemical Communications 64, no. 5 (1999): 883–94. http://dx.doi.org/10.1135/cccc19990883.

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The reaction of [M(μ-Cl)(cod)]2 (M = Rh, Ir; cod = cycloocta-1,5-diene) with two equivalents of the lithium ortho-carboranethiolate derivative LiCabN,S 2 [LiCabN,S = closo-2-(dimethylaminomethyl)-1-(lithiumthiolato)-ortho-carborane] produced the four-coordinated metallacyclic compounds, CabN,SM(cod) 3 (M = Rh 3a, Ir 3b), in which the metal atom was stabilized via intramolecular N,S-coordination. These new compounds have been isolated in high yields and characterized by IR and NMR spectroscopy. The structure consists of an amino-ortho-carboranethiolate fragment bonded to (cod)Rh(I) via nitrogen and sulfur, so as to give the metal a square-planar environment. Subsequent carbonylation reactions of 3a, 3b result in the quantitative formation of the corresponding (amino-ortho-carboranethiolato)(carbonyl)metal N,S-chelates CabN,SM(CO)2 4 (M = Rh 4a, Ir 4b). The metal carbonyl complexes 4a, 4b have been isolated and characterized by spectroscopic and compound 4a also by X-ray diffraction techniques. The molecular structure of 4a reveals that the rhodium atom is coordinated by nitrogen and sulfur atoms of the amino-ortho-carboranethiolate ligand, and two carbonyl ligands complete the coordination of the metal atom.
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27

Sandeep, Paloth Venugopalan, and Anil Kumar. "Metal Free, Direct and Selective Deoxygenation of α-Hydroxy Carbonyl Compounds: Access to α,α-Diaryl Carbonyl Compounds." European Journal of Organic Chemistry 2020, no. 17 (April 21, 2020): 2530–36. http://dx.doi.org/10.1002/ejoc.202000142.

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28

Fujihara, Tetsuaki, and Yasushi Tsuji. "Transition-metal Catalyzed Synthesis of Carbonyl Compounds Using Formates or Formamides as Carbonyl Sources." Journal of the Japan Petroleum Institute 61, no. 1 (January 1, 2018): 1–9. http://dx.doi.org/10.1627/jpi.61.1.

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29

Heilweil, E. J., J. C. Stephenson, and R. R. Cavanagh. "Measurements of carbonyl(v = 1) population lifetimes: metal-carbonyl cluster compounds supported on silica." Journal of Physical Chemistry 92, no. 21 (October 1988): 6099–103. http://dx.doi.org/10.1021/j100332a050.

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30

Wang, Hongyan, Yaoming Xie, R. Bruce King, and Henry F. Schaefer. "Vanadium Carbonyl Nitrosyl Compounds: The Carbonyl Nitrosyl Chemistry of an Oxophilic Early Transition Metal." European Journal of Inorganic Chemistry 2009, no. 12 (April 2009): 1647–56. http://dx.doi.org/10.1002/ejic.200801175.

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31

Kohls, Emilija, and Matthias Stein. "VIBRATIONAL SCALING FACTORS FOR Rh(I) CARBONYL COMPOUNDS IN HOMOGENEOUS CATALYSIS." Contributions, Section of Natural, Mathematical and Biotechnical Sciences 38, no. 1 (June 19, 2017): 43. http://dx.doi.org/10.20903/csnmbs.masa.2017.38.1.100.

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Metal carbonyl complexes are an important family of catalysts in homogeneous industrial processes. Their characteristic vibrational frequencies allow in situ tracking of catalytic progress. Structural assignment of intermedi-ates is often hampered by the lack of appropriate reference compounds. The calculation of carbonyl vibrational fre-quencies from first principles provides an alternative tool to identify such reactive intermediates. Scaling factors for computed vibrational carbonyl stretching frequencies were derived from a training set of 45 Rh-carbonyl complexes using the BP86 and B3LYP functionals. The systematic scaling of the computed C=O frequencies yields accurate calculation and assignment of the experimentally obtained 𝜈(CO) values. The vibrational scaling factors can be used to identify reaction intermediates of the industrially relevant Rh-catalyzed hydroformylation reaction. The absolute error between calculated and experimental spectra was significantly reduced and the experimental spectra were as-signed successfully.
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32

Yan, Guobing, and Arun Jyoti Borah. "Transition-metal-catalyzed direct β-functionalization of simple carbonyl compounds." Org. Chem. Front. 1, no. 7 (2014): 838–42. http://dx.doi.org/10.1039/c4qo00154k.

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Chemical transformations via catalytic C–H bond activation have been established as one of the most powerful tools in organic synthetic chemistry. Transition-metal-catalyzed direct functionalization of β-C(sp3)–H bonds of carbonyl compounds has been developed in recent years. This highlight will focus on recent advances in this active area and their mechanisms are also discussed.
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33

Reinfandt, Niklas, and Peter W. Roesky. "Reactivity of a Sterical Flexible Pentabenzylcyclopentadienyl Samarocene." Inorganics 10, no. 2 (February 18, 2022): 25. http://dx.doi.org/10.3390/inorganics10020025.

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Reactivity studies of the classical divalent lanthanide compound [CpBz52Sm] (CpBz5 = pentabenzylcyclopentadienyl-anion) towards diphenyl dichalcogenides and d-element carbonyl complexes led to remarkable results. In the compounds obtained, a different number of Sm-C(phenyl) interactions and differently oriented benzyl groups were observed, suggesting—despite the preference of these interactions in [CpBz52Sm] described in previous studies—a flexible orientation of the benzyl groups and thus a variable steric shielding of the metal center by the ligand. The obtained compounds are either present as monometallic complexes (reduction of the dichalcogenides) or tetrametallic bridged compounds in the case of the d/f-element carbonyl complexes.
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34

Bayer, Uwe, and Reiner Anwander. "Carbonyl group and carbon dioxide activation by rare-earth-metal complexes." Dalton Transactions 49, no. 48 (2020): 17472–93. http://dx.doi.org/10.1039/d0dt03578e.

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Not just hilariously effective baits! Rare-earth-metal compounds selectively react with aldehydes, ketones and carbon dioxide to generate isolable compounds as crucial intermediates in organic synthesis and homogenous catalysis.
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35

Vikrant, Kumar, Yao Qu, Jan E. Szulejko, Vanish Kumar, Kowsalya Vellingiri, Danil W. Boukhvalov, Taejin Kim, and Ki-Hyun Kim. "Utilization of metal–organic frameworks for the adsorptive removal of an aliphatic aldehyde mixture in the gas phase." Nanoscale 12, no. 15 (2020): 8330–43. http://dx.doi.org/10.1039/d0nr00234h.

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36

Huang, Xi, Junjie Hu, Mengying Wu, Jiayi Wang, Yanqing Peng, and Gonghua Song. "Catalyst-free chemoselective conjugate addition and reduction of α,β-unsaturated carbonyl compounds via a controllable boration/protodeboronation cascade pathway." Green Chemistry 20, no. 1 (2018): 255–60. http://dx.doi.org/10.1039/c7gc02863f.

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37

Enow, Charles A., Charlene Marais, and Barend C. B. Bezuidenhoudt. "Catalytic epoxidation of stilbenes with non-peripherally alkyl substituted carbonyl ruthenium phthalocyanine complexes." Journal of Porphyrins and Phthalocyanines 16, no. 04 (April 2012): 403–12. http://dx.doi.org/10.1142/s1088424612500459.

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A number of novel carbonyl(1,4,8,11,15,18,22,25-octaalkylphthalocyaninato)-ruthenium(II) complexes were prepared by metal insertion with Ru3(CO)12. The new compounds have been characterized by1H NMR,13C NMR, IR, UV-vis and mass spectroscopy. This study demonstrated that this type of complexes and specifically carbonyl(1,4,8,11,15,18,22,25-octahexylphthalo-cyaninato)ruthenium(II) and carbonyl[1,4,8,11,15,18,22,25-octa(2-cyclohexylethyl)phthalocyaninato]-ruthenium(II), exhibit high catalytic activity and stability in the epoxidation of stilbenes with 2,6-dichloropyridine N-oxide as oxidant.
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38

Massolo, Elisabetta, Margherita Pirola, Sergio Rossi, and Tiziana Benincori. "Metal-Free Alpha Trifluoromethylselenolation of Carbonyl Derivatives under Batch and Flow Conditions." Molecules 24, no. 4 (February 18, 2019): 726. http://dx.doi.org/10.3390/molecules24040726.

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Trifluoromethylselenolated carbonyl compounds represent an emerging class with potential applications in several fields; however, a widespread use of such compound is hampered by the very limited number of strategies for their preparation. In this study we developed a method for the preparation of α-SeCF3 substituted carbonyl derivatives using an in situ generated electrophilic ClSeCF3 species. We also implemented an in-flow protocol to improve the safety features of the process.
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39

Hall, Dennis G. "New preparative methods for allylic boronates and their application in stereoselective catalytic allylborations." Pure and Applied Chemistry 80, no. 5 (January 1, 2008): 913–27. http://dx.doi.org/10.1351/pac200880050913.

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Stereocontrolled additions of allylic metal reagents to carbonyl compounds constitute one of the most useful classes of transformations in organic synthesis. The recent development of Lewis and Brønsted acid-catalyzed manifolds for the allylboration of carbonyl compounds has opened doors toward an ideal carbonyl allylation methodology using stable and nontoxic allylic boronates as reagents. This paper describes the development of acid-catalyzed allylborations, mechanistic investigations of these new processes, and ongoing efforts toward general catalytic enantioselective allylboration methodologies. The preparation of optically enriched α-substituted allylic boronate reagents is discussed, as well as their applications in Lewis acid-catalyzed additions to afford skeletally diverse products like propionate units, polysubstituted furans, vinylcyclopropanes, and larger ring systems.
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40

Knorr, Rudolf, and Barbara Schmidt. "Nucleofugal behavior of a β-shielded α-cyanovinyl carbanion." Beilstein Journal of Organic Chemistry 14 (December 11, 2018): 3018–24. http://dx.doi.org/10.3762/bjoc.14.281.

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Sterically well-shielded against unsolicited Michael addition and polymerization reactions, α-metalated α-(1,1,3,3-tetramethylindan-2-ylidene)acetonitriles added reversibly to three small aldehydes and two bulky ketones at room temperature. Experimental conditions were determined for transfer of the nucleofugal title carbanion unit between different carbonyl compounds. These readily occurring retro-additions via C–C(O) bond fission may also be used to generate different metal derivatives of the nucleofugal anions as equilibrium components. Fluoride-catalyzed, metal-free desilylation admitted carbonyl addition but blocked the retro-addition.
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41

van Hal, Jaap W., Lawrence B. Alemany, and Kenton H. Whitmire. "Solution Dynamics of Thallium−Metal Carbonyl Compounds Using205Tl NMR Spectroscopy." Inorganic Chemistry 36, no. 14 (July 1997): 3152–59. http://dx.doi.org/10.1021/ic961203k.

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42

Sivaramakrishna, Akella, Paul Mushonga, Ian L. Rogers, Feng Zheng, Raymond J. Haines, Ebbe Nordlander, and John R. Moss. "Selective isomerization of 1-alkenes by binary metal carbonyl compounds." Polyhedron 27, no. 7 (May 2008): 1911–16. http://dx.doi.org/10.1016/j.poly.2008.02.026.

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43

Mead, Keith, and Timothy L. Macdonald. "Metal ion controlled addition to .alpha.,.beta.-dialkoxy carbonyl compounds." Journal of Organic Chemistry 50, no. 3 (February 1985): 422–24. http://dx.doi.org/10.1021/jo00203a040.

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44

Ji, Shun-Jun, and Lin Wu. "Acetalization of carbonyl compounds catalyzed by polymer-bound metal complexes." Journal of Molecular Catalysis A: Chemical 202, no. 1-2 (August 2003): 41–46. http://dx.doi.org/10.1016/s1381-1169(03)00210-3.

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Trapp, I., T. Famulok, U. Risse, and A. Kettrup. "FTIR-screening of carbonyl compounds in metal working fluid aerosols." Fresenius' Journal of Analytical Chemistry 362, no. 4 (October 13, 1998): 409–14. http://dx.doi.org/10.1007/s002160051095.

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Ma, Zhi-Hong, Ming-Xia Zhao, Fang Li, Hong Wang, Xue-Zhong Zheng, and Jin Lin. "Synthesis and structures of substituted tetramethylcyclopentadienyl dinuclear metal carbonyl compounds." Transition Metal Chemistry 35, no. 4 (February 21, 2010): 387–91. http://dx.doi.org/10.1007/s11243-010-9339-0.

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Nishino, Toshiki, Yutaka Nishiyama, and Noboru Sonoda. "ChemInform Abstract: Reductive Coupling of Carbonyl Compounds Using Lanthanum Metal." ChemInform 31, no. 16 (June 9, 2010): no. http://dx.doi.org/10.1002/chin.200016051.

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Pichon, Maëva M., Damien Hazelard, and Philippe Compain. "Metal-Free Deoxygenation of α-Hydroxy Carbonyl Compounds and Beyond." European Journal of Organic Chemistry 2019, no. 37 (August 28, 2019): 6320–32. http://dx.doi.org/10.1002/ejoc.201900838.

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Pihko, Petri M. "Enantioselective α-Fluorination of Carbonyl Compounds: Organocatalysis or Metal Catalysis?" Angewandte Chemie International Edition 45, no. 4 (January 16, 2006): 544–47. http://dx.doi.org/10.1002/anie.200502425.

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Harinath, Adimulam, Jayeeta Bhattacharjee, Hari Pada Nayek, and Tarun K. Panda. "Alkali metal complexes as efficient catalysts for hydroboration and cyanosilylation of carbonyl compounds." Dalton Transactions 47, no. 36 (2018): 12613–22. http://dx.doi.org/10.1039/c8dt02032a.

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Abstract:
Catalytic hydroboration of aldehydes and ketones with pinacolborane (HBpin) and catalytic cyanosilylation of carbonyl compounds with trimethylsilyl cyanide using alkali metal (Li, Na, K) complexes as precatalysts under mild conditions are reported.
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