Academic literature on the topic 'Oxirane compounds'

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Journal articles on the topic "Oxirane compounds"

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Rinald, Andrew, Victor Terskikh, Gabriele Schatte, and Gang Wu. "A combined solid-state 17O NMR, crystallographic, and computational study of oxiranes." Canadian Journal of Chemistry 98, no. 8 (August 2020): 434–40. http://dx.doi.org/10.1139/cjc-2020-0114.

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We report the synthesis and solid-state 17O NMR characterization of three 17O-labeled oxiranes: (2S*,3S*)-2,3-bis(4-nitrophenyl)-[17O]oxirane, (2S*,3R*)-2,3-bis(4-nitrophenyl)-[17O]oxirane, and 2,2,3-triphenyl-[17O]oxirane. In addition, we have determined the crystal structure of (2S*,3R*)-2,3-bis(4-nitrophenyl)oxirane by X-ray crystallography. When the experimentally determined 17O NMR tensors for oxiranes (where the C–O–C bond angle is about 60°) are compared with those for dimethyl ether (where the C–O–C bond angle is 113°) and other R–O–R′ functional groups, we found that the highly constrained geometry of oxiranes results in distinct tensor orientations in the molecular frame of reference. The experimental results are complemented by quantum chemical computations. This study represents the first time that 17O chemical shift and quadrupole coupling tensors are simultaneously determined for oxirane compounds.
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Dawid, Malgorzata, and John Warkentin. "Intramolecular reactions of dialkoxycarbenes with a carbonyl group." Canadian Journal of Chemistry 81, no. 6 (June 1, 2003): 598–606. http://dx.doi.org/10.1139/v02-200.

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Thermolysis of 5,5-dimethyl-2-methoxy-2-(2-oxocyclohexylmethoxy)-Δ3-1,3,4-oxadiazoline (3a) in benzene at 110°C generated a carbonyl ylide intermediate that gave, in a minor side reaction, a product of 1,3-dipolar cycloaddition to the carbonyl group. The major fate of the ylide was fragmentation to acetone and a dialkoxycarbene, MeO (RCH2O)C:, where R = 2-oxocyclohexyl. The carbene, in turn, underwent overall [2 + 1] cycloaddition to the carbonyl group, presumably to afford diastereomeric dialkoxyoxiranes that could not be isolated. A product of methanolysis of the presumed oxiranes was isolated by GC and its structure was determined by means of X-ray diffraction. Methanol is believed to result from reaction of an intermediate or product with adventitious water. Deliberate hydrolysis of the product of methanolysis gave a hydroxy lactone, the structure of which was also secured by means of single crystal X-ray diffraction. Those structures indicated the likely structures of the oxirane precursors. A second, and major, product from the carbene was a bicyclic ketone. Similar products were obtained from intramolecular reactions of a carbene tethered to cyclopentanone through a two-carbon or a one-carbon tether. Some compounds that are apparently "dimers" of the oxiranes were also isolated and identified by means of X-ray diffraction. These dimers are thought to originate from the reaction of a ring-opened oxirane (a dipole or a cation from electrophilic opening of the oxirane) with a molecule of the oxirane rather than from bimolecular reaction between two oxirane molecules. The oxiranes open by cleavage of the (RO)2C—O bond rather than the oxirane C—C bond, the normally observed sense of thermal ring opening. The properties of the carbenes and the presumed oxiranes serve to point out the options available to such intermediates and suggest that some new, synthetically useful reactions may become possible.Key words: bicyclic ketone, dialkoxycarbene, dialkoxyoxirane, hydroxylactone, "oxirane dimers".
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Khalili, Gholamhossein, Patrick McCosker, Timothy Clark, and Paul Keller. "Synthesis and Density Functional Theory Studies of Azirinyl and Oxiranyl Functionalized Isoindigo and (3Z,3’Z)-3,3’-(ethane-1,2-diylidene)bis(indolin-2-one) Derivatives." Molecules 24, no. 20 (October 10, 2019): 3649. http://dx.doi.org/10.3390/molecules24203649.

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The design and synthesis of functionalized isoindigo compounds by reaction of isoindigo with (S)-glycidyl tosylate, epibromohydrin, 2-(bromomethyl)-1-(arylsulfonyl)aziridine, and 2-(bromomethyl)-1-(alkylsulfonyl)aziridine in the presence of MeONa proceed under mild conditions in moderate yields. (3Z,3’Z)-3,3’-(Ethane-1,2-diylidene)bis(1-(oxiran-2-ylmethyl)indolin-2-one), with an extended central olefin π-conjugated moiety was also reacted with methyl-oxiranes to give the corresponding N,N’-disubstituted derivative. Calculations with DFT and TD-DFT of hypothetical isoindigo-thiophene DA molecules with various electron withdrawing substituents, including aziridine, oxirane, nitrile, carbonyl, and sulfonate, indicated that the proximity and strength of the functional group have a significant effect on the HOMO, LUMO, vertical excitation energy, and oscillator strength of the π–π* transitions.
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David, Michèle, Jean Sauleau, and Armelle Sauleau. "Époxydes α-éthyléniques et phénate de sodium: accès à des éthers phénoliques et phénols ortho-allyliques." Canadian Journal of Chemistry 63, no. 9 (September 1, 1985): 2449–54. http://dx.doi.org/10.1139/v85-405.

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The ring cleavage reactions of α-ethylenic epoxides by sodium phenoxide afforded a mixture of products. Problems of competitive attack by this nucleophile, at the less substituted carbon (compounds A) or at the β-ethylenic carbon atom (compounds B and C), were encountered and could be resolved by judicious choice of reaction conditions (solvents, stereochemistry of the oxiranes). The regioselectivity of the attack was dependent on the transition states, implying weak steric hindrance and a conjugation oxirane – double bond.
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Weigand, Wolfgang, Ulrich Nagel, and Wolfgang Beck. "Pseudohalogeno-Metallverbindungen, LXVIII [1]. Reaktionen der Cyanometallsäuren NCAuCNH, (NC)4Pt(CNH)2, (NC)2M(CNH)4(M = Fe, Ru, Os) und Co[bis(dimethyIglyoximato)](CN)CNHmit Epoxiden: 2-Hydroxyalkylisocyanid- und Oxazolidin-2-yIiden-MetalIkomplexe / Pseudohalogeno Metal Compounds, LXVIII [1]. Reaction of Cyano Metal Acids NCAuCNH, (NC)4Pt(CNH)2, (NC)2M(CNH)4 (M = Fe, Ru, Os) and Co[bis(dimethylglyoximato)](CN)CNH with Epoxides: 2-Hydroxyalkylisocyanide and Oxazolidine-2-ylidene Metal Complexes." Zeitschrift für Naturforschung B 43, no. 3 (March 1, 1988): 328–38. http://dx.doi.org/10.1515/znb-1988-0316.

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NCAuCNH reacts with expoxides to give oxazolidine-2-ylidene (2) and 2-hydroxyalkyl complexes (3), respectively. Complexes with cyclic carbene ligands [XXX] (5) and [XXX] (7) are formed from the corresponding isocyanic metal compounds and oxiranes. 5b has been characterized by crystal structure determination. Ring opening of phenyloxirane occurs at the phenyl substituted carbon atom. (NC)2M(CNH)4 (M = Fe, Ru, Os) and oxirane yield mixtures of [XXX] and [XXX].
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El-Sayed, Amira A., Maher A, El Hashash, and Sameh A. Rizk. "Ultrasonic and solvent free Synthesis of Regioselective Diastereomeric Adducts and Heterocyclic Products as antibacterial agent." JOURNAL OF ADVANCES IN CHEMISTRY 13, no. 2 (June 9, 2017): 5977–88. http://dx.doi.org/10.24297/jac.v13i12.6152.

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Oxirane ring containing the carboxylic group in the α,β-position are useful intermediates in the synthesis of biologically active compounds. Epoxidation of 4-(4-acetylamino and/or bromophenyl)-4-oxo-but-2-enoic acids via ultrasound condition afforded α-oxirane carboxylic acid followed by regioselective diastereomeric adducts of camphor. The steric factor plays an important role in regioselectivity. Formation of oxirane and furan derivatives via ultrasonic condition was considered as key steps for synthesis of some important heterocyclic compounds. The structure of new synthesized compounds 2-9a,b were elucidated by elemental analysis and spectroscopic data. The antibacterial activity for the synthesized compounds was evaluated.
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Gyuranová, Dominika, Radka Štadániová, Zuzana Hegyi, Róbert Fischer, and Martin Rebroš. "Production of Enantiopure Chiral Epoxides with E. coli Expressing Styrene Monooxygenase." Molecules 26, no. 6 (March 10, 2021): 1514. http://dx.doi.org/10.3390/molecules26061514.

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Styrene monooxygenases are a group of highly selective enzymes able to catalyse the epoxidation of alkenes to corresponding chiral epoxides in excellent enantiopurity. Chiral compounds containing oxirane ring or products of their hydrolysis represent key building blocks and precursors in organic synthesis in the pharmaceutical industry, and many of them are produced on an industrial scale. Two-component recombinant styrene monooxygenase (SMO) from Marinobacterium litorale was expressed as a fused protein (StyAL2StyB) in Escherichia coli BL21(DE3). By high cell density fermentation, 35 gDCW/L of biomass with overexpressed SMO was produced. SMO exhibited excellent stability, broad substrate specificity, and enantioselectivity, as it remained active for months and converted a group of alkenes to corresponding chiral epoxides in high enantiomeric excess (˃95–99% ee). Optically pure (S)-4-chlorostyrene oxide, (S)-allylbenzene oxide, (2R,5R)-1,2:5,6-diepoxyhexane, 2-(3-bromopropyl)oxirane, and (S)-4-(oxiran-2-yl)butan-1-ol were prepared by whole-cell SMO.
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Askerov, O. V., A. F. Mamedova, and D. R. Nurullayeva. "SYNTHESIS AND PROPERTIES OF ORGANOSILICON EPISULFIDES." Azerbaijan Chemical Journal, no. 4 (December 8, 2021): 43–48. http://dx.doi.org/10.32737/0005-2531-2021-4-43-48.

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A study was made of the interaction of thiourea with saturated and unsaturated organosilicon oxiranes in absolute methyl alcohol in a medium of potassium hydroxide, and methods were developed for the synthesis of unsaturated and unsaturated organosilicon silicides with a yield of 65–75%.The studies carried out revealed that the synthesized organosilicon episulfides are very reactive compounds and can react with nucleophilic and electrophilic reagents, while forming the corresponding silicon derivatives. The IR- spectra of the products were studied. It should be noted that, when comparing the IR- spectra of oxiranes and episulfides, it was revealed that the stretching vibrations of the CH2 group of the episulfide ring are underestimated by 50–70 cm-1 in comparison with the oxirane ring
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Tan, Xiaojun, Mengyao Wu, Yilin Wang, Guizhi Shi, and Jinsong Gu. "Theoretical study on the reaction between silacyclopropenylidene and three-membered heterocyclic compounds (azirane and oxirane): An alternative approach to the formation of heterocyclic silylene." Progress in Reaction Kinetics and Mechanism 45 (January 2020): 146867832090205. http://dx.doi.org/10.1177/1468678320902059.

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The reaction mechanism between silacyclopropenylidene and three-membered heterocyclic compounds (azirane and oxirane) has been systematically investigated at the B3LYP/6-311+G* level of theory in order to better understand the reactivity of unsaturated cyclic silylene. Geometry optimizations and vibrational analyses have been conducted for the stationary points on the potential energy surface of the system. Calculations show that the Si-spiroheterocyclic intermediate and four-membered heterocyclic silylene compound could be produced through the insertion process and subsequent dissociation process between silacyclopropenylidene and three-membered heterocyclic compounds. For the insertion process, it is easier for silacyclopropenylidene to insert into C-N bond of azirane than into C-O bond of oxirane. This study is helpful to understand the reactivity of silacyclopropenylidene, the evolution of silicon-bearing molecules in space, and to offer an alternative approach to the formation of enlarged heterocyclic silylene compound.
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Emblem, H. G., and N. A. Hurt. "Reactions of aminoalkyl silicates with oxirane compounds." Journal of Applied Chemistry 12, no. 8 (May 4, 2007): 366–73. http://dx.doi.org/10.1002/jctb.5010120805.

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Dissertations / Theses on the topic "Oxirane compounds"

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Jachiet, Denis. "Reactivite des organocuprates et des organoaluminates associes a bf::(3) dans l'ouverture nucleophile des oxirannes : application a la synthese de pheromones." Paris 6, 1987. http://www.theses.fr/1987PA066438.

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Soutif, Jean-Claude. "Etude de l'addition des acides carboxyliques sur les structures oxiranne : application aux polymeres epoxydes." Le Mans, 1987. http://www.theses.fr/1987LEMA1010.

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La modification chimique au deuxieme degre de polymeres epoxydes a ete etudiee pour developper une methode de fixation de principes actifs (medicaments, colorants, complexants) comportant des fonctions acides, sur des supports macromoleculaires. Le catalyseur est un sel de tetramethylammonium de l'acide a fixer. Epoxydation de polyisoprene et polybutadiene
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Pale, Patrick. "Synthese et reactivite d'epoxyalcools acetyleniques chiraux : application a la synthese de cyclopropanes et d'heterocycles fonctionnalises." Reims, 1988. http://www.theses.fr/1988REIMS012.

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Bernadet, Philippe. "Propriétés spectroscopiques de complexes formes entre un hydracide (HCl, HBr, HI)) et l'oxyde d'éthylène (EO) en matrice d'argon et d'azote : analyse du profil de la bande d'absorption HCl des complexes H(D)Cl:EO et H(D)Cl:dimethylether et étude." Paris 6, 1986. http://www.theses.fr/1986PA066355.

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Book chapters on the topic "Oxirane compounds"

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Bartók, M., and K. L. Láng. "Oxiranes." In Chemistry of Heterocyclic Compounds: A Series Of Monographs, 1–196. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2008. http://dx.doi.org/10.1002/9780470187203.ch1.

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Gudat, D. "From Metal Phosphides and Oxiranes." In Organophosphorus Compounds (incl. RO-P and RN-P), 1. Georg Thieme Verlag KG, 2009. http://dx.doi.org/10.1055/sos-sd-042-00155.

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"Product Class 2: Epoxides (Oxiranes)." In Category 5, Compounds with One Saturated Carbon Heteroatom Bond, edited by Forsyth. Stuttgart: Georg Thieme Verlag, 2008. http://dx.doi.org/10.1055/sos-sd-037-00140.

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"1.2.2. Reaction of Oxiranes with Carbanions." In Carbocyclic Three- and Four-Membered Ring Compounds, edited by Armin de Meijere. Stuttgart: Georg Thieme Verlag, 1997. http://dx.doi.org/10.1055/b-0035-113162.

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Jung, K. W., and A. S. Nagle. "Conversion of Thiones into Carbonyl Compounds Using Oxiranes." In Four Carbon-Heteroatom Bonds, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-018-00523.

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Sato, S., and N. Furukawa. "Cyclization of Oxiranes, Thiiranes, and Acetylenic Compounds with Carbon Disulfide." In Four Carbon-Heteroatom Bonds, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-018-01025.

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"Hydrazone or Oxirne and Ring-Carbon or Ring-Nitrogen." In Chemistry of Heterocyclic Compounds: A Series Of Monographs, 1260–66. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2008. http://dx.doi.org/10.1002/9780470187319.ch95.

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Hashmi, A. S. K. "Bromoallenes by Alkynylogous Ring Opening of Oxiranes." In X-Ene-X (X=F, Cl, Br, I, O, S, Se, Te, N, P), Ene-Hal, and Ene-O Compounds, 1. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-032-00039.

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Oshima, K. "Exocyclic Fischer Carbene Complexes by Reaction of Dibromoalkanes, Aziridines, or Oxiranes with Carbonylmanganese Complexes." In Compounds of Groups 7-3 (Mn..., Cr..., V..., Ti..., Sc..., La..., Ac...), 1. Georg Thieme Verlag KG, 2003. http://dx.doi.org/10.1055/sos-sd-002-00035.

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Taber, Douglass. "Preparation of Heteroaromatics." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0068.

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Masahiro Yoshida of the University of Tokushima described (Tetrahedron Lett. 2008, 49, 5021) the Pt-mediated rearrangement of alkynyl oxiranes such as 1 to the furan 2. Roman Dembinski of Oakland University reported (J. Org. Chem. 2008, 73, 5881) a related zinc-mediated rearrangement of propargyl ketones to furans. The cyclization of aryloxy ketones such as 3 to the benzofuran 4 developed (Tetrahedron Lett. 2008, 49, 6579) by Ikyon Kim of the Korea Research Institute of Chemical Technology is likely proceeding by a Friedel-Crafts mechanism. Sandro Cacchi and Giancarlo Fabrizi of Università degli Studi “La Sapienza”, Roma, observed (Organic Lett. 2008, 10, 2629) that base converted the enamine 5 to the pyrrole 6. Alternatively, oxidation of 5 with CuBr led to a pyridine. Zhuang-ping Zhuan of Xiamen University prepared (Adv. Synth. Cat. 2008, 350, 2778) pyrroles such as 9 by condensing an alkynyl carbinol 7 with a 1,3-dicarbonyl compound. Richard C. Larock of Iowa State University found (J. Org. Chem. 2008, 73, 6666) that combination of an alkynyl ketone 10 with 11 followed by oxidation with I-Cl led to the pyrazole 12. The “click” condensation of azides with alkynes, leading to the 1,4-disubstituted 1,2,3- triazole, has proven to be a powerful tool for combinatorial synthesis. Valery V. Fokin of Scripps/La Jolla and Zhenyang Lin and Guochen Jia of the Hong Kong University of Science and Technology have developed (J. Am. Chem. Soc. 2008, 130, 8923) a complementary approach, using Ru catalysts to prepare 1,5-disubstituted 1,2,3- triazoles. Remarkably, internal alkynes participate, and, as in the conversion of 13 to 15, propargylic alcohols direct the regioselectivity of the cycloaddition. A variety of methods have been put forward for functionalizing pyridines. Sukbok Chang of KAIST described (J. Am. Chem. Soc. 2008, 130, 9254) the direct oxidative homologation of a pyridine N -oxide 16 to give the unsaturated ester 18. Jonathan Clayden of the University of Manchester observed (Organic Lett. 2008, 10, 3567) that metalation of 19 gave an anion that rearranged to 20 with complete retention of enantiomeric excess. Shigeo Katsumura of Kwansei Gakuin University developed (Tetrahedron Lett. 2008, 49, 4349) an intriguing three-component coupling, combining 21, 22, and methanesulonamide 23 to give the pyridine 24.
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