Relevant bibliographies by topics / Carbenes (Methylene compounds)

Academic literature on the topic 'Carbenes (Methylene compounds)'

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Published: 4 June 2021
Last updated: 28 July 2024

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Journal articles on the topic "Carbenes (Methylene compounds)"

1

Kidonakis, Marios, and Manolis Stratakis. "Reduction of the Diazo Functionality of α-Diazocarbonyl Compounds into a Methylene Group by NH3BH3 or NaBH4 Catalyzed by Au Nanoparticles." Nanomaterials 11, no. 1 (January 18, 2021): 248. http://dx.doi.org/10.3390/nano11010248.

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Supported Au nanoparticles on TiO2 (1 mol%) are capable of catalyzing the reduction of the carbene-like diazo functionality of α-diazocarbonyl compounds into a methylene group [C=(N2) → CH2] by NH3BH3 or NaBH4 in methanol as solvent. The Au-catalyzed reduction that occurs within a few minutes at room temperature formally requires one hydride equivalent (B-H) and one proton that originates from the protic solvent. This pathway is in contrast to the Pt/CeO2-catalyzed reaction of α-diazocarbonyl compounds with NH3BH3 in methanol, which leads to the corresponding hydrazones instead. Under our stoichiometric Au-catalyzed reaction conditions, the ketone-type carbonyls remain intact, which is in contrast to the uncatalyzed conditions where they are selectively reduced by the boron hydride reagent. It is proposed that the transformation occurs via the formation of chemisorbed carbenes on Au nanoparticles, having proximally activated the boron hydride reagent. This protocol is the first general example of catalytic transfer hydrogenation of the carbene-like α -ketodiazo functionality.
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Mbuvi, Harun M., Erik R. Klobukowski, Gina M. Roberts, and L. Keith Woo. "O-H insertion and tandem N-H insertion/cyclization reactions using an iron porphyrin as catalyst with diazo compounds as carbene sources." Journal of Porphyrins and Phthalocyanines 14, no. 03 (March 2010): 284–92. http://dx.doi.org/10.1142/s1088424610001982.

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Iron(III) tetraphenylporphyrin chloride, Fe(TPP)Cl , efficiently catalyzed the insertion of carbenes derived from methyl 2-phenyldiazoacetates into O-H bonds of aliphatic and aromatic alcohols, with yields generally above 80%. Although the analogous N-H insertions are rapid at room temperature, the O-H insertion reactions are slower and required heating in refluxing methylene chloride for about 8 hours using 1.0 mol.% catalyst. Fe(TPP)Cl was also found to be effective for tandem N-H insertion/cyclization reactions when 1,2-diamines and 1,2-alcoholamines were treated with diazo reagents to give piperazinones and morpholinones and related analogs such as quinoxalinones and benzoxazin-2-ones. This approach provides a new one-pot route for synthesizing these classes of heterocyclic compounds.
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3

Zoghbi, Michel, and John Warkentin. "Azetinone formation is not competitive with intermolecular reactions of a β-lactam-4-ylidene." Canadian Journal of Chemistry 70, no. 11 (November 1, 1992): 2792–97. http://dx.doi.org/10.1139/v92-355.

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3-Phenoxy-1-phenyl-2-azetidinon-4-ylidene (β-lactam-4-ylidene) 2a, was generated by thermolysis of a spiro-fused β-lactam oxadiazoline precursor (1). Fast 1,2-H migration, a characteristic reaction of singlet carbenes that would convert 2a to 3-phenoxy-1-phenyl-3-azetin-2-one (4a) could not be demonstrated. Added 1, 3-diphenylisobenzofuran (6) did not afford the [4 + 2] cycloadduct (7) expected from 4a but, instead, the isomeric E- and Z-4-[1-(2-benzoylphenyl)-1-phenyl]-methylene-3-phenoxy-1-phenylazetidin-2-ones (9). Those compounds can be rationalized as the products of rearrangement of first-formed [2 + 1] adducts of 6 and the ylidene. The structure of the Z isomer of 9 was established by means of single crystal X-ray diffraction. Generation of 2a in methanol-d4, either neat or 3.3 M in benzene, afforded the isomeric products of carbene insertion into the OD bond of methanol-d4. Structural isomers expected from addition of methanol-d4 to 4a could not be detected. The results suggest that 1,2-H migration in 2a is relatively slow, with kH ≤ 1.4 × 106 s−1 at 100 °C, which is slower than analogous rearrangement of benzylchlorocarbene by 200-fold or more.
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4

Kysilka, Ondřej, Markéta Rybáčková, Martin Skalický, Magdalena Kvíčalová, Josef Cvačka, and Jaroslav Kvíčala. "HFPO Trimer-Based Alkyl Triflate, a Novel Building Block for Fluorous Chemistry. Preparation, Reactions and 19F gCOSY Analysis." Collection of Czechoslovak Chemical Communications 73, no. 12 (2008): 1799–813. http://dx.doi.org/10.1135/cccc20081799.

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Triflate 4, CF3(CF2)2O-CF(CF3)CF2O-CF(CF3)CH2-OTf (RFOCH2OTf), of the HFPO trimer-based alcohol 3 (RFOCH2OH) is a novel highly fluorinated building block for fluorous chemistry. In analogy to similar polyfluorinated triflates with methylene spacer, its reactivity is limited to strong and soft nucleophiles. Whereas reactions with cyanide anion, phenolate anion, enolate of diethyl malonate or lithium salt of benzaldehyde bis(phenylsulfanyl)acetal were unsuccessful, the corresponding imidazole 5, iodide 6 or azide 7 were prepared in good yields. Reaction of imidazole 5 with (perfluorohexyl)methyl triflate (9) afforded highly fluorinated non-crystalline imidazolium salt 8, TfO-RFOCH2-(C3H3N2)+-CH2C6F13-n, which could be employed as fluorous ionic liquid or intermediate for fluorous carbenes. Complete assignment of complex 19F NMR spectra of all compounds employed was accomplished using 19F gCOSY NMR method.
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5

Monopoli, Antonio, Pietro Cotugno, Carlo Giorgio Zambonin, Francesco Ciminale, and Angelo Nacci. "Highly selective palladium–benzothiazole carbene-catalyzed allylation of active methylene compounds under neutral conditions." Beilstein Journal of Organic Chemistry 11 (June 10, 2015): 994–99. http://dx.doi.org/10.3762/bjoc.11.111.

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The Pd–benzothiazol-2-ylidene complex I was found to be a chemoselective catalyst for the Tsuji–Trost allylation of active methylene compounds carried out under neutral conditions and using carbonates as allylating agents. The proposed protocol consists in a simplified procedure adopting an in situ prepared catalyst from Pd2dba3 and 3-methylbenzothiazolium salt V as precursors. A comparison of the performance of benzothiazole carbene with phosphanes and an analogous imidazolium carbene ligand is also proposed.
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6

Amer, Atef Mohamed, Mohamed Fouad Zayed, Ali Deeb, and Ahmed Ali. "Pyridazine derivatives and related compounds. Part 141. Photolysis of 3-diazo-4,5-diphenylpyrazolo[3,4-c]pyridazine." Journal of Chemical Research 2005, no. 10 (October 2005): 643–47. http://dx.doi.org/10.3184/030823405774663011.

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The photochemistry of 3-diazopyrazolopyridazine has been investigated. The irradiation of 3-diazo-4,5-diphenylpyrazolo[3,4-c]pyridazine in various solvents forms a carbene intermediate, which transforms into 3-substituted derivatives. For photolysis in the presence of acetylacetone or ethyl acetoacetate the coupling reactions which occur at the methylene group are faster than carbene formation, and can lead to direct cyclisation into condensed 1,2,4-triazines. Photolysis in the presence of diethyl malonate forms an acyclic hydrazone.
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7

Chetcuti, Michael J., Haithem Naghmouchi, Abdelwaheb Hamdi, and Lydia Karmazin. "Synthesis of Imidazolium Cations Linked to Para-t-Butylcalix[4]arene Frameworks and Their Use as Synthons for Nickel-NHC Complexes Tethered to Calix[4]arenes." Molecules 28, no. 15 (July 27, 2023): 5697. http://dx.doi.org/10.3390/molecules28155697.

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A series of cationic p-tert-butylcalix[4]arenes, with side-arms that are functionalized with imidazolium groups, have been synthesized in good yields. The parent tetrahydroxy para-t-butyl-calix[4]arene was dialkylated at the phenolic hydrogen atoms using α,ω-dibromo-alkanes to yield bis(mono-brominated) alkoxy-chains of variable length. The brominated side-arms in these compounds were then further alkylated with substituted imidazoles (N-methylimidazole, N-(2,4,6-trimethyl-phenyl)imidazole, or N-(2,6-di-isopropylphenyl)imidazole) to yield a series of dicationic calixarenes with two imidazolium groups tethered, via different numbers of methylene spacers (n = 2–4), to the calixarene moiety. Related tetracationic compounds, which contain four imidazolium units linked to the calix[4]arene backbone, were also prepared. In all of these compounds, the NMR data show that the calixarenes adopted a cone configuration. All molecules were characterized by NMR spectroscopy and by MS studies. Single crystal X-ray diffraction studies were attempted on many mono-crystals of these cations, but significant disorder problems, partly caused by occluded solvent in the lattice, and lack of crystallinity resulting from partial solvent loss, precluded the good resolution of most X-ray structures. Eventually, good structural data were obtained from an unusually disordered single crystal of 5a, (1,3)-Cone-5,11,17,23-tetra-t-butyl-25,27-di-hydroxy-26,28-di-[2-(N-2,6-diisopropylphenyl-imidazolium)ethoxy]calix[4]arene dibromide and its presumed structure was confirmed. The structure revealed the presence of H-bonded interactions and some evidence of π-stacking. Some of these imidazolium salts were reacted with nickelocene to form the nickel N-heterocyclic carbene (NHC) complexes 7a–7d. A bis-carbene nickel complex 8 was also isolated and its structure was established by single crystal X-ray diffraction studies. The structure was disordered and not of high quality, but the structural data corroborated the spectroscopic data.
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8

Monopoli, Antonio, Pietro Cotugno, Carlo Giorgio Zambonin, Francesco Ciminale, and Angelo Nacci. "ChemInform Abstract: Highly Selective Palladium-Benzothiazole Carbene-Catalyzed Allylation of Active Methylene Compounds under Neutral Conditions." ChemInform 46, no. 34 (August 2015): no. http://dx.doi.org/10.1002/chin.201534057.

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9

Singh, Shailesh, Jyoti Tiwari, Deepali Jaiswal, Amit Kumar Sharma, Jaya Singh, Vandana Singh, and Jagdamba Singh. "Nucleophilic Acylation with Aromatic Aldehydes to 2 Bromoacetonitrile: An Umpolung Strategy for the Synthesis of Active Methylene Compounds." Current Organic Synthesis 17, no. 7 (October 28, 2020): 518–24. http://dx.doi.org/10.2174/1570179417666200615153536.

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Background: A novel one-pot N-heterocyclic carbene (NHC)-catalysed acylation of 2- bromoacetonitrile with aromatic aldehydes is reported. The protocol involves carbonyl umpolung reactivity of aldehydes in which the carbonyl carbon attacks nucleophilically (as d1 nucleophile) on the electrophilic terminal of 2-bromoacetonitrile to afford 3-aryl-3-oxopropanenitrile. The salient features of this procedure are short reaction time, operational simplicity, ambient temperature, no by-product formation and high yields. Materials and Methods: A flame-dried round bottom flask was charged with Imidazolium salts (3a) (0.20 mmol). Aldehyde 1a (1.0 mmol), 2-bromoacetonitrile 2 (1.0 mmol), and THF / t-BuOH 5 mL; 10:1) were added at positive nitrogen pressure followed by the addition of DBU (0.15 mmol) through stirring. The resulting yellow- orange solution was stirred at room temperature for 5-6 h. After completion of the reaction (TLC monitored), the reaction mixture was concentrated under reduced pressure. The product was purified using hexane / EtOAc (10:1) as an eluent to provide analytically pure compound 4a. Physical data of representative compounds and the NMR spectroscopic data are in agreement with the literature value. Results and Discussion: The salient features of this procedure are short reaction time, operational simplicity, ambient temperature, no by-product formation and high yields. Conclusion: To sum up, we have developed a convenient, efficient and one-pot route for 3-oxo-3- phenylpropanenitrile synthesis from NHC promoted direct nucleophilic acylation of aromatic aldehydes using 2- bromoacetonitrile. This method provided a wide range of products and good yields. To best of our knowledge, this is the new report for the synthesis of 3-oxo-3-phenylpropanenitrile through NHC promoted nucleophilic acylation of aromatic aldehyde.
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10

Terada, Yukiyoshi, Mitsuhiro Arisawa, and Atsushi Nishida. "Cycloisomerization Promoted by the Combination of a Ruthenium–Carbene Catalyst and Trimethylsilyl Vinyl Ether, and its Application in The Synthesis of Heterocyclic Compounds: 3-Methylene-2,3-dihydroindoles and 3-Methylene-2,3-dihydrobenzofurans." Angewandte Chemie International Edition 43, no. 31 (August 6, 2004): 4063–67. http://dx.doi.org/10.1002/anie.200454157.

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Dissertations / Theses on the topic "Carbenes (Methylene compounds)"

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Moeng, Mmushi Moses. "Terthienyl carbene complexes." Diss., Pretoria : [s.n.], 2001. http://upetd.up.ac.za/thesis/available/etd-02092006-153600/.

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Lu, Xiaosong. "Generation and reactions of aryloxy and diaryloxycarbenes /." *McMaster only, 2001.

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3

Frankowski, Kevin J. "Carbenes and carbenoids as powerful tools in organic synthesis." Access to citation, abstract and download form provided by ProQuest Information and Learning Company; downloadable PDF file 2.18 Mb., 94 p, 2006. http://gateway.proquest.com/openurl?url_ver=Z39.88-2004&res_dat=xri:pqdiss&rft_val_fmt=info:ofi/fmt:kev:mtx:dissertation&rft_dat=xri:pqdiss:3205422.

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Merkley, Nadine. "Carbenes and radicals from benzyloxy [delta]3-1,3,4-oxadiazolines /." *McMaster only, 2001.

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Thesis (Ph.D.) -- McMaster University, 2001.
[Delta] in title is a Greek letter. The number 3 in title is superscript. Includes bibliographical references (leaves 147-162). Also available via World Wide Web.
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5

El-Saidi, Manal M. T. "Synthesis and thermolysis of 2,2-dioxy-5,5-dimethyl-[delta three]-1,3,4-oxadiazolines : dioxycarbenes and their reactions /." *McMaster only, 1996.

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Couture, Philippe. "Syntheses and reactions of aminooxycarbenes from thermolysis of [Delta3]-1,3,4-oxadiazolines /." *McMaster only, 1997.

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Lian, Yiqian. "Chromium and iron organometallics in organic synthesis synthetic studies toward total synthesis of taxol and chromium to iron transfer processes /." Diss., Connect to online resource - MSU authorized users, 2006.

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Asay, Matt J. "Ylides stabilization of novel, low valent carbon-based ligands with applications in catalysis /." Diss., [Riverside, Calif.] : University of California, Riverside, 2009. http://gateway.proquest.com/openurl?url_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:dissertation&res_dat=xri:pqdiss&rft_dat=xri:pqdiss:3350076.

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Thesis (Ph. D.)--University of California, Riverside, 2009.
Includes abstract. Title from first page of PDF file (viewed Mar. 8, 2010). Includes bibliographical references. Issued in print and online. Available via ProQuest Digital Dissertations.
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Rafael, Christopher Carlos Ferreira. "Synthesis of chromium carbene scaffolds for use in medicinal chemistry." Thesis, Rhodes University, 2014. http://hdl.handle.net/10962/d1010863.

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This study involves using methyllithium to synthesize Fischer carbene complexes as precursors for metal templated α,β-unsaturated complexes with potential as acceptors in the Baylis Hillman reaction as well as in Dötz benzannulation. Fischer carbene complexes contain low oxidation state metal centers, are electrophilic in nature and are stabilized by π-donating substituents such as alkoxy and amino groups. The increased electron withdrawing nature of the metal carbonyl moiety was expected to improve the rates of reaction compared to organic carbonyls. Four Fischer carbenes were synthesized via nucleophilic addition of MeLi to chromium and tungsten hexacarbonyl at low temperatures followed by alkylation using either a Meerwein salt (Me₃OBF₄) to give the desired Fischer metal methyl methoxy carbenes or Et₄NBr/alkylhalide to make the corresponding ethoxy and allyloxy carbenes. Characterization was by means of ¹³C NMR, ¹H NMR, and IR. In silico studies were carried out looking at the effect of substituents on the carbene bond. Synthesis of α,β-unsaturated complexes was effected via the aldol condensation route and found to be unfavorable using enolizable aldehydes, although the use of two aryl aldehydes resulted in successful preparation of two α,β-unsaturated complexes. Difficulty in the purification of these complexes hindered their full characterization. Computational studies looked at the effect of substituents on the system as well as variation of the metal from Cr to Mo and W. Synthesis of Baylis Hillman adducts using α,β-unsaturated complexes as acceptors was unsuccessful due to the ease of product oxidization. One potential product was obtained in its crude form although purification was not possible due to oxidation. Computational studies suggested that the oxygen on the ligand negatively impacts the stability of these Fischer carbene derived Baylis Hillman adducts promoting intramolecular oxidation of the metal. The α,β-unsaturated complexes and Baylis Hillman adducts were considered to be candidates to undergo Dötz benzannulation methodology. The use of the α,β-unsaturated complexes in this reaction was generally unsuccessful, both in the microwave and in conventional reflux conditions. Computational studies of these compounds were carried out to facilitate understanding of their stability and configuration.
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Olivier, Andrew John. "Novel carbene complexes with pyrrole ligands." Diss., Pretoria : [s.n, 2001. http://upetd.up.ac.za/thesis/available/etd-02242006-125303/.

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Books on the topic "Carbenes (Methylene compounds)"

1

Nefedov, O. M. Khimii͡a︡ karbenov. Moskva: Khimii͡a︡, 1990.

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M, Nefedov O., and Rassadin B. V, eds. Chemistry of carbenes and small-sized cyclic compounds. Moscow: Mir Publishers, 1989.

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G, Bertrand, ed. Carbene chemistry: From fleeting intermediates to powerful reagents. New York: Marcel Dekker, 2002.

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N-heterocyclic carbenes: From laboratory curiosities to efficient synthetic tools. Cambridge: Royal Society of Chemistry, 2011.

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S, Platz Matthew, ed. Kinetics and spectroscopy of carbenes and biradicals. New York, London: Plenum Press, 1990.

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Cazin, Catherine Suzanne Julienne. N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis. Dordrecht: Springer Science+Business Media B.V., 2011.

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Kirmse, Wolfgang. Carbene Chemistry. Elsevier Science & Technology Books, 2013.

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Kirmse, Wolfgang. Carbene Chemistry. Elsevier Science & Technology Books, 2012.

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Nolan, Steven P. N-Heterocyclic Carbenes in Synthesis. Wiley-VCH, 2006.

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Carbenes Nitrenes and Arynes. Springer, 2014.

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