Relevant bibliographies by topics / Hydroformylation of Alkenes

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Academic literature on the topic 'Hydroformylation of Alkenes'

Author: Grafiati
Published: 6 September 2023

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Journal articles on the topic "Hydroformylation of Alkenes"

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Shi, Yukun, Yang Lu, Tongxin Ren, Jie Li, Qiqige Hu, Xiaojing Hu, Baolin Zhu, and Weiping Huang. "Rh Particles Supported on Sulfated g-C3N4: A Highly Efficient and Recyclable Heterogeneous Catalyst for Alkene Hydroformylation." Catalysts 10, no. 11 (November 23, 2020): 1359. http://dx.doi.org/10.3390/catal10111359.

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The hydroformylation of alkenes with CO and H2 to manufacture aldehydes is one of the most large-scale chemical reactions. However, an efficient and recyclable heterogeneous catalyst for alkene hydroformylation is extremely in demand in academia and industry. In this study, a sulfated carbon nitride supported rhodium particle catalyst (Rh/S-g-C3N4) was successfully synthesized via an impregnation-borohydride reduction method and applied in the hydroformylation of alkenes. The catalysts were characterized by XRD, FTIR, SEM, TEM, XPS, and nitrogen adsorption. The influence of the sulfate content, pressure of syngas, temperature, and reaction time, as well as the stability of Rh/S-g-C3N4, on the hydroformylation was examined in detail. The delocalized conjugated structure in g-C3N4 can lead to the formation of electron-deficient aromatic intermediates with alkenes. The sulphate g-C3N4 has a defected surface owing to the formation of oxygen vacancies, which increased the adsorption and dispersion of RhNPs on the surface of g-C3N4. Therefore, Rh/S-g-C3N4 exhibited an outstanding catalytic performance for styrene hydroformylation (TOF = 9000 h−1), the conversion of styrene could reach 99.9%, and the regioselectivity for the branched aldehyde was 52% under the optimized reaction conditions. The catalytic properties of Rh/S-g-C3N4 were also studied in the hydroformylation of various alkenes and displayed an excellent catalytic performance. Furthermore, the reuse of Rh/S-g-C3N4 was tested for five recycling processes, without an obvious decrease in the activity and selectivity under the optimum reaction conditions. These findings demonstrated that Rh/S-g-C3N4 is a potential catalyst for heterogeneous hydroformylation.
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Doyle, MM, WR Jackson, and P. Perlmutter. "The Stereochemistry of Organometallic Compounds. XXXIV. Regioselection in the Hydroformylation of Silylalkenes." Australian Journal of Chemistry 42, no. 11 (1989): 1907. http://dx.doi.org/10.1071/ch9891907.

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The regiochemistry of hydroformylation of alkenes can be controlled by the use of bulky silyl groups attached to the alkene. Use of the t-butyldiphenylsilyl group leads to almost total regiocontrol and the method has been applied to the synthesis of aldols.
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Hood, Drew M., Ryan A. Johnson, Alex E. Carpenter, Jarod M. Younker, David J. Vinyard, and George G. Stanley. "Highly active cationic cobalt(II) hydroformylation catalysts." Science 367, no. 6477 (January 30, 2020): 542–48. http://dx.doi.org/10.1126/science.aaw7742.

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The cobalt complexes HCo(CO)4 and HCo(CO)3(PR3) were the original industrial catalysts used for the hydroformylation of alkenes through reaction with hydrogen and carbon monoxide to produce aldehydes. More recent and expensive rhodium-phosphine catalysts are hundreds of times more active and operate under considerably lower pressures. Cationic cobalt(II) bisphosphine hydrido-carbonyl catalysts that are far more active than traditional neutral cobalt(I) catalysts and approach rhodium catalysts in activity are reported here. These catalysts have low linear-to-branched (L:B) regioselectivity for simple linear alkenes. However, owing to their high alkene isomerization activity and increased steric effects due to the bisphosphine ligand, they have high L:B selectivities for internal alkenes with alkyl branches. These catalysts exhibit long lifetimes and substantial resistance to degradation reactions.
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Yu, Xuetong, Yuxia Ji, Yan Jiang, Rui Lang, Yanxiong Fang, and Botao Qiao. "Recent Development of Single-Atom Catalysis for the Functionalization of Alkenes." Catalysts 13, no. 4 (April 12, 2023): 730. http://dx.doi.org/10.3390/catal13040730.

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The functionalization of alkenes is one of the most important conversions in synthetic chemistry to prepare numerous fine chemicals. Typical procedures, such as hydrosilylation and hydroformylation, are traditionally catalyzed using homogeneous noble metal complexes, while the highly reactive and stable heterogeneous single-atom catalysts (SACs) now provide alternative approaches to fulfill these conversions by combining the advantages of both homogeneous catalysts and heterogeneous nanoparticle catalysts. In this review, the recent achievement in single-atom catalyzed hydrosilylation and hydroformylation reactions are introduced, and we highlight the latest applications of SACs for additive reactions, constructing new C-Y (Y = B, P, S, N) bonds on the terminal carbon atoms of alkenes, and then mention the applications in single-metal-atom catalyzed hydrogenation and epoxidation reactions. We also note that some tandem reactions are conveniently realized in one pot by the concisely fabricated SACs, facilitating the preparation of some pharmaceutical compounds. Lastly, the challenges facing single-atom catalysis for alkene conversions are briefly mentioned.
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Geng, Hui-Qing, Tim Meyer, Robert Franke, and Xiao-Feng Wu. "Copper-catalyzed hydroformylation and hydroxymethylation of styrenes." Chemical Science 12, no. 44 (2021): 14937–43. http://dx.doi.org/10.1039/d1sc05474k.

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Peral, Daniel, Daniel Herrera, Julio Real, Teresa Flor, and J. Carles Bayón. "Strong π-acceptor sulfonated phosphines in biphasic rhodium-catalyzed hydroformylation of polar alkenes." Catalysis Science & Technology 6, no. 3 (2016): 800–808. http://dx.doi.org/10.1039/c5cy01004g.

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Chevry, M., T. Vanbésien, S. Menuel, E. Monflier, and F. Hapiot. "Tetronics/cyclodextrin-based hydrogels as catalyst-containing media for the hydroformylation of higher olefins." Catalysis Science & Technology 7, no. 1 (2017): 114–23. http://dx.doi.org/10.1039/c6cy02070d.

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Shi, Yukun, Gang Ji, Qiqige Hu, Yang Lu, Xiaojing Hu, Baolin Zhu, and Weiping Huang. "Highly uniform Rh nanoparticles supported on boron doped g-C3N4 as a highly efficient and recyclable catalyst for heterogeneous hydroformylation of alkenes." New Journal of Chemistry 44, no. 1 (2020): 20–23. http://dx.doi.org/10.1039/c9nj05385a.

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Wu, Lipeng, Qiang Liu, Anke Spannenberg, Ralf Jackstell, and Matthias Beller. "Highly regioselective osmium-catalyzed hydroformylation." Chemical Communications 51, no. 15 (2015): 3080–82. http://dx.doi.org/10.1039/c4cc05626d.

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Osmium carbonyl combined with 2-imidazoyl-substituted phosphine ligands forms active species for the highly regioselective and general hydroformylation of alkenes to produce aldehydes in good yields and excellent regioselectivities. An unusual phosphido bridged trinuclear osmium catalyst structure was obtained.
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Nandakumar, Avanashiappan, Manoj K. Sahoo, and Ekambaram Balaraman. "Reverse-hydroformylation: a missing reaction explored." Organic Chemistry Frontiers 2, no. 10 (2015): 1422–24. http://dx.doi.org/10.1039/c5qo00229j.

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Recent progress in transition-metal catalysed acceptor- and acceptorless-reverse hydroformylation of aldehydes for the conversion of olefins has been discussed. The aldehyde feedstock serves as a source for production of syngas and valuable alkenes.
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Dissertations / Theses on the topic "Hydroformylation of Alkenes"

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Iu, Leo. "New catalysts for branched selective hydroformylation of alkenes." Thesis, University of St Andrews, 2019. http://hdl.handle.net/10023/17068.

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Both products, n-butyraldehyde and iso-butyraldehyde from propene hydroformylation are key building blocks for the synthesis of many chemical intermediates, and although high linear selectivity has been achieved, any form of branched selectivity remains very difficult to attain. This project aims to deliver a catalyst that can selectively produce branched iso-butyraldehyde as the major product from propene hydroformylation. One approach discussed is to study terphenyl phosphines as ligands. The synthesis of substituted terphenyls through Suzuki-Miyaura coupling reactions between aryl boronic acids and 2,6-dichloroanisole was studied. Novel phosphine-phosphanamine ligands with bulky terphenyl substituents were synthesised and tested in propene hydroformylation, and also asymmetric hydroformylation of other alkenes. The synthesis of several ferrocene-based phosphine-phosphoramidite ligands is also discussed. These ligands were then tested in rhodium-catalysed propene hydroformylation and their reactivities and selectivities are reported. These ligands/Rh catalysts showed a moderate reactivity for propene hydroformylation and up to 56% branched selectivity, which is close to the best selectivity known under industrially relevant conditions. The introduction of bulky substituents on the phosphoramidite part of the ligand did not deliver any huge increases in regioselectivity, but a large improvement in catalyst thermal stability was observed in experiments conducted using in situ high pressure infrared spectroscopy. The reaction conditions for rhodium-catalysed propene hydroformylation using the BOBPHOS ligand were investigated, with unprecedented branched selectivity of up to 82% achieved. A variety of aspects was examined, including the solvent, reaction temperature, reaction pressure with varying partial pressure of CO and H₂, and rhodium to ligand ratio. BOBPHOS derivatives which are more synthetically accessible and economically attractive were synthesised and tested in rhodium-catalysed propene hydroformylation. Comparable results with their parent ligand/Rh catalyst were obtained and improved thermal stabilities were observed in selected catalysts. Different directions for potential future works are suggested, which hopefully, along with the findings in this thesis, can be a major contribution to the development of an efficient, branched selective catalytic system for industrial propene hydroformylation.
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Osuna, Anna Maria Banet. "Hydroformylation of higher and functionalised alkenes in supercritical carbon dioxide." Thesis, University of Liverpool, 2001. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.343988.

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Annis, Alexandra H. "The Development of Rhodium-Catalyzed Asymmetric Hydroformylation of 1-Alkenes to Access Chiral Aldehydes." Thesis, Boston College, 2015. http://hdl.handle.net/2345/bc-ir:104636.

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Thesis advisor: James Morken
Asymmetric hydroformylation (AHF) is a metal-catalyzed reaction in which CO and H2 are added across an olefin to form a new carbon-carbon bond. AHF has perfect atom-economy and is an ideal way to form a chiral aldehyde. However, the utility of branch selective hydroformylation is limited due to a lack of readily available ligands and restrictions on a wide variety of terminal olefins. Herein, Rh-catalyzed asymmetric hydroformylation of 1-alkenes is reported using commercially available Ph-BPE ligand to generate α-chiral aldehydes. A wide range of terminal olefins were explored and all showed high enantioselectivity (up to 98:2 er) and good regioselectivity (up to 15:1 branched to linear ratio)
Thesis (MS) — Boston College, 2015
Submitted to: Boston College. Graduate School of Arts and Sciences
Discipline: Chemistry
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Desset, Simon L. "New strategies for the rhodium-catalysed aqeous-biphasic hydroformylation of medium chain alkenes /." St Andrews, 2009. http://hdl.handle.net/10023/842.

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Desset, Simon L. "New strategies for the rhodium-catalysed aqueous-biphasic hydroformylation of medium chain alkenes." Thesis, University of St Andrews, 2009. http://hdl.handle.net/10023/842.

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Aqueous-biphasic organometallic catalysis is, as illustrated by the industrial hydroformylation of propene and butene, one of the most promising ways to overcome the intrinsic problem of catalyst separation in organometallic catalysis. However, for poorly water-soluble substrates, mass transfer limitations bring the reaction rate below any that could be economically viable, greatly limiting the scope of this elegant technology. We have studied three different strategies to overcome this limitation. We developed additives that speed up the reaction whilst retaining fast phase separation and good metal retention. Evidence suggests that those additives affect the reaction by forming emulsions with poor stability under the reaction conditions These emulsions increase the interfacial surface area but break after settling for a short time. We also developed ligands that allow the catalyst to be reversibly transported between an aqueous and an organic phase upon addition and removal of carbon dioxide. This allows the reaction to be carried out under homogeneous conditions, only limited by intrinsic kinetics, and the catalyst to be separated by aqueous extraction triggered by carbon dioxide. The catalyst can be returned to a fresh organic phase by flushing out the carbon dioxide. By applying this methodology for the hydroformylation of medium chain length alkenes, very high reaction rates were obtained and the catalyst could be recycle three times with excellent retention of activity and low metal leaching. This methodology could also be reversed with the reaction being carried out in an aqueous phase in the presence of carbon dioxide and extracting the catalyst into an organic solvent using nitrogen flushing. Finally, we briefly investigated the use of an oscillatory baffled reactor as a mean for mass transfer improvement for aqueous-biphasic hydroformylation. This new type reactor did not improve the performance of the system under the investigated conditions, but may require less energy input for equivalent agitation and mixing.
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Gong, Zhenxin. "Continuous flow homogeneous hydroformylation of 1-octene over supported ionic liquid phase rhodium catalysts using supercritical CO₂." Thesis, University of St Andrews, 2011. http://hdl.handle.net/10023/1877.

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The hydroformylation of 1-octene with supported ionic liquid phase catalyst was demonstrated when using a system involving the substrate, reacting gases and products in CO₂ and N₂ flow over a fixed bed supported ionic liquid phase catalyst (silica gel and carbon aerogels as solid support respectively) at different system pressures. Yields, reaction rates, selectivities and rhodium leaching were all monitored. A pressure of CO₂ flow just below the critical point of the flowing mixture (106 bar at 100 °C if no 1-octene has been converted) was the best condition for the hydroformylation. It gave the highest acitivity (conversion to aldehyde up to 70 %), fastest reaction (TOF up to 575.3 h⁻¹) and best stable selectivity ( l:b ratio reaching 3.37 ). The utilization of scCO₂ as reaction media leads to remarkable stability of the catalyst. The supercritical or near critical (expanded liquid) system completely overcame the progressive decrease in activity of catalyst at 50, 75 bar with liquid phase transport and also showed much better results than when using other gas flows such as N₂ flow at 100 bar. In the high pressure scCO₂ phase, the concentration of 1-octene at the catalyst bed was reduced so that the conversion to aldehyde was reduced. The pore size and surface groups of the solid support should be suitable for the SILP catalyst consisting of metal complex, excess ligand and ionic liquid. Using microporous carbon aerogels as the supports, whether activated or not, gave disappointing results.
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Bronger, Raymond Petrus Johannes. "Selective hydroformylation of internal alkenes to linear aldehydes novel phosphacyclic diphosphines and their applications /." [S.l. : Amsterdam : s.n.] ; Universiteit van Amsterdam [Host], 2004. http://dare.uva.nl/document/75911.

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Sun, Xixi. "Scaffolding Catalysis: Towards Regioselective Hydroformylation of Alkenes and Site-Selective Functionalization of Polyhydroxylated Molecules." Thesis, Boston College, 2013. http://hdl.handle.net/2345/3324.

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Thesis advisor: Kian L. Tan
Chapter 1. We reported the first synthesis of all-carbon quaternary centers via hydroformylations using a catalytic directing group. With the ability of reversibly and covalently binding to a substrate, and coordinating to a metal center, scaffolding catalyst 1.1 is able to direct the branch-selective hydroformylation of 1,1-disubstituted olefins under mild temperature. Chapter 2. We have designed and synthesized a chiral organocatalyst 2.11. This catalyst is able to covalently bind to one hydroxyl, and utilize the induced intramolecularity to stereoselectively functionalize the other hydroxyl within a cis-1,2-diol via electrophile transfer. Catalyst 2.11 was used in the desymmetrization of meso-1,2-diols under mild conditions (4 C to room temperature), leading to high yields and selectivities for a broad substrate scope. Chapter 3. Catalyst 3.1 and 3.6 were demonstrated to selectively bind to primary hydroxyls over secondary hydroxyls. By combining the binding selectivity with asymmetric catalysis, these scaffolding catalysts were shown to promote the selective silylation of secondary hydroxyls within terminal (S)-1,2-diols. The reversal of substrate bias was further applied to a regiodivergent kinetic resolution of racemic terminal 1,2-diols, producing secondary protected products in synthetically practical levels of enantioselectivity (>95:5 er) and yields (≥40%). Time course studies of this reaction further revealed the optimal condition to form the primary silylated product in high s-factor. Chapter 4. Based on the previous understanding of catalyst 4.5 and 4.6, the exclusive catalyst recognition of cis-1,2-diols within polyhydroxylated molecules was further discovered. This unique functional group display recognition was further allied with the catalyst's ability to stereoselectively differentiate hydroxyls within cis-1,2-diols, enabling the site-selective protection, functionalization, and activation of the inherently less reactive axial hydroxyl groups within carbohydrates. This methodology also enables the selective functionalization of multiple complex molecules, including digoxin, mupirocin, and ribonucleosides, demonstrating the potential power of scaffolding catalysis in the rapid access to valuable synthetic derivatives of polyhydroxylated compounds
Thesis (PhD) — Boston College, 2013
Submitted to: Boston College. Graduate School of Arts and Sciences
Discipline: Chemistry
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Guo, Ipin. "Hydroformylation of olefins by water soluble and asymmetric cobalt and platinum complexes." Diss., Virginia Tech, 1991. http://hdl.handle.net/10919/39855.

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Hydroformylation of olefins (OXO synthesis), one of the oldest organometallic catalytic reactions, continues to be of interest because of its commercial significance. Great interest recently has been placed on the development of immobilized homogeneous catalysts that combine the virtues of conventional heterogeneous and homogeneous catalysts. The objective of this dissertation is to investigate novel phosphine modified water soluble cobalt and platinum complexes as homogeneous and immobilized hydroformylation catalysts. The ligands include (1) Monodentate phosphines: P[ (CH₂ ) n-C₆H₄-S0₃Na] ₃ (n = 0-3) and P[C₆H₄-NMe₃⁺BF₄⁻]₃; (2) Bidentate asymmetric phosphines: CHlRAPHOS(NMe₂)₄ (CHlRAPHOS = 2, 3-bis (diphenylphosphino) butane) , SKEWPHOS (NMe₂)₄ (SKEWPHOS = 2,4-bis(diphenylphospino)pentane), and DlOP(NMe₂)₄ (DlOP = 2,2-dimethyl-4,5-bis(diphenyl(phosphinomethyl)-1,3- dioxolane) ). These complexes were immobilized and/or recycled by four different methods: (1) Two phase catalysis; (2) Supported aqueous phase catalysis; (3) Catalyst supported on ion exchange resins; (4) Extraction of the catalyst from an organic phase into an aqueous phase. Catalytic results for the hydroformylation of a-olefins shows that nib (normal:branch of aldehyde product) ratio can be increased if proper alkyl-phosphine ligands are chosen. For example, as high as 18.5 of nib ratio was obtained in PtCl[P(C₆H₅)₃]₂-snCl₃ system and 5.6 in CO₂ (CO) ₆ [TRlMAPP] ₂ (TRlMAPP = trimethylamino-phenylphosphine) system. Metal leaching, from the aqueous phase to the organic phase during the catalytic reaction, was reduced by supporting the water soluble cobalt and platinum complexes onto a high surface area glass (CGP-350). For instance, 5.7% cobalt metal was found in the organic phase when CO₂(CO)₆(TPPTS)₂ was used under reaction conditions (TPPTS = triphenylphosphine trisulphonated salt). When the same cobalt complex was immobilized on glass, no cobalt metal leaching was observed. Asymmetric hydroformylation of styrene catalyzed by PtCl [SKEWPHOS (NMe₂) ₄] -SnCl₃ shows a very strong temperature dependence on optical selectivity. Enantiomeric excess (ee's) switches sign from S to R form at 57°C. At 25°C, there is 60.6% ee of S product, whereas 56.7% ee in favor of R product is observed at 100°C.
Ph. D.
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Du, Toit Judith G. O. "Use of water-soluble phosphine ligands in heterogeneous hydroformylation catalysis : application to long-chain 1-alkenes." Master's thesis, University of Cape Town, 1994. http://hdl.handle.net/11427/22055.

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The two-phase rhodium-tri(m-sulfonatophenyl)phosphine (Rh-TPPTS) system for the hydroformylation of 1-octene, 1-decene, and 1-dodecene to the corresponding aldehydes, has been investigated. Due to the two distinct phases - the catalytic species in the aqueous phase and the products and reactants in the organic phase - the separation of the catalyst was easily facilitated. A comparison was made of the activity, selectivity towards linear aldehydes, and catalyst lifetime of two systems where i) the active catalytic species were generated in situ from rhodium trichloride (RhCl₃.3H₂O) and excess phosphine ligand (TPPTS) under mild hydroformylation conditions (5 MPa H₂/CO (1:1); 100 °C); and ii) where the rhodium(I) complex, RhH(CO)(TPPTS)₃ is used as the catalyst precursor. The former system was found to be superior in activity and selectivity to that of the latter, achieving fairly high conversions of ca. 60% for the hydroformylation of 1-octene, with n:iso ratios of up to 16:1 for a catalyst composition a Rh:P ratio of 1:30. Unfortunately low conversions of ca. 10% for the hydroformylation of 1-decene and ca. 4% for that of 1-dodecene resulted under the same conditions. While the reasons for the drastic decrease in conversion for C₁₀ and C₁₂ alkenes is not completely clear, this poor conversion is attributed to the extremely low solubility of the long-chain 1-alkenes in the aqueous phase. Under certain optimum conditions (Rh:P ≥ l :20), virtually no leeching of rhodium into the organic phase was detected. A ³¹P NMR spectroscopic study was undertaken in an attempt to ascertain the nature and distribution of rhodium tertiary-phosphine complexes in the aqueous phase before and after the mixture was subjected to standard hydroformylation conditions.
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Books on the topic "Hydroformylation of Alkenes"

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Naughton, Michael J. The hydroformylation of olefins using supported film catalysts. 1993.

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Book chapters on the topic "Hydroformylation of Alkenes"

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Breit, Bernhard. "Directed Rhodium-Catalyzed Hydroformylation of Alkenes." In Topics in Organometallic Chemistry, 145–68. Berlin, Heidelberg: Springer Berlin Heidelberg, 2007. http://dx.doi.org/10.1007/3418_2007_067.

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Mika, L. T., and I. T. Horváth. "Hydroformylation of Higher Alkenes." In Water in Organic Synthesis, 1. Georg Thieme Verlag KG, 2012. http://dx.doi.org/10.1055/sos-sd-206-00114.

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Mika, L. T., and I. T. Horváth. "Hydroformylation of Functionalized Alkenes." In Water in Organic Synthesis, 1. Georg Thieme Verlag KG, 2012. http://dx.doi.org/10.1055/sos-sd-206-00115.

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"Asymmetric Hydroformylation of Alkenes." In C-1 Building Blocks in Organic Synthesis 1, edited by van Leeuwen. Stuttgart: Georg Thieme Verlag, 2014. http://dx.doi.org/10.1055/sos-sd-212-00020.

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"Tandem Hydroformylation of Alkenes." In C-1 Building Blocks in Organic Synthesis 1, edited by van Leeuwen. Stuttgart: Georg Thieme Verlag, 2014. http://dx.doi.org/10.1055/sos-sd-212-00055.

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Taber, Douglass. "Selective Reactions of Alkenes." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0023.

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Fabio Doctorovich of the Universidad de Buenos Aires reported (J. Org. Chem. 2008, 73, 5379) that hydroxylamine in the presence of an Fe catalyst reduced alkenes such as 1, but not ketones or esters. Erick Carreira of ETH Zürich developed (Angew. Chem. Int. Ed. 2008, 47, 5758) mild conditions for the hydrochlorination of mono-, di- and trisubstituted alkenes. Ramgopal Bhattacharyya of Jadavpur University established (Tetrahedron Lett. 2008, 49, 6205) a simple Mo-catalyzed protocol for alkene epoxidation. Nitro alkenes are of increasing importance as acceptors for enantioselective organocatalyzed carbon-carbon bond formation. Matthias Beller of the Universität Rostock found (Adv. Synth. Cat. 2008, 350, 2493) that an alkene such as 7 was readily converted to the corresponding nitroalkene 8 by exposure to of NO gas. The reaction could also be effected with NaNO2/HOAC. Two complementary protocols for Rh-catalyzed alkene hydroformylation have been reported. Xumu Zhang of Rutgers University devised (Organic Lett. 2008, 10, 3469) a ligand system that cleanly migrated the alkene of 9, then terminally hydroformylated the resulting monosubstituted alkene, to give 10. Kian L. Tan of Boston College designed (J. Am. Chem. Soc. 2008, 130, 9210) a ligand such that the hydroformylation of the internal alkene of 11 was directed to the end of the alkene proximal to the directing OH, delivering 12. Several other methods for the functionalizing homologation of alkenes have been put forward. Chul-Ho Jun of Yonsei University assembled (J. Org. Chem. 2008, 73, 5598) a Rh catalyst that effected the oxidative acylation of a terminal alkene 13 with a primary benzylic alcohol, to give the ketone 14. For now, this approach is limited to less expensive alkenes, as the alkene, used in excess, is the reductant in the reaction. The other procedures outlined here require only stoichiometric alkene. Yasuhiro Shiraishi of Osaka University devised (Organic Lett. 2008, 10, 3117) a simple photoprocess for adding acetone to a terminal alkene 13 to give the methyl ketone 14, in what is presumably a free radical reaction.
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Fiaud, J. C., and A. Marinetti. "Rhodium-Promoted Hydroformylation of Alkenes." In Organophosphorus Compounds (incl. RO-P and RN-P), 1. Georg Thieme Verlag KG, 2009. http://dx.doi.org/10.1055/sos-sd-042-00505.

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"Synthesis by Hydroformylation of Alkenes." In Category 4, Compounds with Two Carbon Heteroatom Bonds, edited by Brückner. Stuttgart: Georg Thieme Verlag, 2007. http://dx.doi.org/10.1055/sos-sd-025-00196.

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"Hydroformylation of Alkenes: Industrial Applications." In C-1 Building Blocks in Organic Synthesis 1, edited by van Leeuwen. Stuttgart: Georg Thieme Verlag, 2014. http://dx.doi.org/10.1055/sos-sd-212-00118.

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Joule, J. A. "Variation 5: From Alkenes via Hydroformylation." In Science of Synthesis Knowledge Updates KU 2011/1, 1. Georg Thieme Verlag KG, 2010. http://dx.doi.org/10.1055/sos-sd-110-00020.

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