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Journal articles on the topic 'Oxirana'

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Published: 4 June 2021

Last updated: 1 February 2022

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1

Sung, Kuangsen. "Substituent effects on stability of oxiranes, oxirenes, and dioxiranes." Canadian Journal of Chemistry 78, no. 5 (2000): 562–67. http://dx.doi.org/10.1139/v00-064.

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Homodesmotic reactions were designed to study substituent effects on stability of oxiranes, oxirenes, and dioxiranes. Good or fair correlation between their homodesmotic stabilization energies and Taft's dual-substituent-parameters has been found. Oxiranes are stabilized by σ-donating and π-donating substituents but destabilized by σ-accepting and π-accepting substituents. The π-effects on oxiranes are comparable to σ-effects for π-acceptor substituents and are much stronger than σ-effects for π-donor substituents. Oxirenes are stabilized by σ-donating, π-donating, and π-accepting substituents

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2

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 (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 constr

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3

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 (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 molecul

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4

Dawid, Malgorzata, and John Warkentin. "Intramolecular reactions of dialkoxycarbenes with a carbonyl group." Canadian Journal of Chemistry 81, no. 6 (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 isolat

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5

Couture, Philippe, Manal El-Saidi, and John Warkentin. "Ketene acetals from thermolysis of aryloxy methoxy oxadiazolines. Evidence for carbonyl ylide intermediates." Canadian Journal of Chemistry 75, no. 3 (1997): 326–32. http://dx.doi.org/10.1139/v97-037.

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Thermolysis of oxadiazolines (5) in benzene at 110 °C leads to ketene acetals (11) as minor products. Carbonyl ylide intermediates (6), and oxiranes (7), presumably in equilibrium with those ylides, are implicated as unstable precursors of the ketene acetals although none of the oxiranes (carbonyl protected α-lactones) were isolable and only one of the ketene acetals was isolable in pure form. The evidence points to the two-step sequence of thermolysis of oxadiazolines, namely, initial cycloreversion to N2 and carbonyl ylide (6), rather than concerted fragmentation to N2, acetone, and carbene

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6

Vigier, Jordan, Camille François, Sylvie Pourchet, et al. "Crystal structure of the diglycidyl ether of eugenol." Acta Crystallographica Section E Crystallographic Communications 73, no. 5 (2017): 694–97. http://dx.doi.org/10.1107/s2056989017005370.

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The diepoxy monomer, C13H16O4{DGE-Eu; systematic name: 2-[3-methoxy-4-(oxiran-2-ylmethoxy)benzyl]oxirane}, was synthesized from eugenol by a three-step reaction. It consists of a 1,2,4-trisubstituted benzene ring substituted by diglycidyl ether, a methoxy group and a methyloxirane group. The three-membered oxirane rings are inclined to the benzene ring by 61.0 (3) and 27.9 (3)°. The methylene C atom of one of the two terminal epoxide rings is positionally disordered [refined occupancy ratio = 0.69 (1):0.31 (1)]. In the crystal, molecules are linked by C—H...O hydrogen bonds, forming layers par

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7

Fu, Qin, and Chao-Guo Yan. "Facile synthesis of functionalized spiro[indoline-3,2'-oxiran]-2-ones by Darzens reaction." Beilstein Journal of Organic Chemistry 9 (May 13, 2013): 918–24. http://dx.doi.org/10.3762/bjoc.9.105.

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A series of functionalized spiro[indoline-3,2'-oxiran]-2-ones was efficiently synthesized by Darzens reaction of phenacyl bromides with isatins both with N-alkyl groups and without N-substituent in the presence of potassium carbonate as a base catalyst. When two equivalents phenacyl bromides were used in the reaction, the N-substitution reaction of isatin also finished with the formation of spiro-oxirane-oxindoles.

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8

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 (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 o

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9

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 (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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10

Fernandes, Maria José G., David M. Pereira, Renato B. Pereira, A. Gil Fortes, Elisabete M. S. Castanheira, and M. Sameiro T. Gonçalves. "Synthesis and Insecticidal Activity of O-alkylated Oxirane Eugenol Derivatives." Chemistry Proceedings 3, no. 1 (2020): 36. http://dx.doi.org/10.3390/ecsoc-24-08335.

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The synthesis of three O-alkylated eugenol derivatives, bearing a hydroxypropyl chain and propyl esters, were synthesized and further converted into the corresponding oxiranes. Oxirane derivatives were then evaluated against their effect upon the viability of the insect cell line Sf9 (Spodoptera frugiperda), in comparison with the starting O-alkylates. The results pointing to their potential as bioinsecticides, with structural changes eliciting significant effects in terms of potency.

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11

David, Michèle, Jean Sauleau та Armelle Sauleau. "Époxydes α-éthyléniques et phénate de sodium: accès à des éthers phénoliques et phénols ortho-allyliques". Canadian Journal of Chemistry 63, № 9 (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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12

Song, Tao, Jin-gang Liu, and Shi-yong Yang. "2-(4-{4-[4-(Oxiran-2-ylmethoxy)phenoxy]phenyl}phenoxymethyl)oxirane." Acta Crystallographica Section E Structure Reports Online 68, no. 3 (2012): o719. http://dx.doi.org/10.1107/s1600536812005740.

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13

Perez-Arce, Jonatan, Ander Centeno-Pedrazo, Jalel Labidi, Jose R. Ochoa-Gomez, and Eduardo J. Garcia-Suarez. "Lignin-Based Polyols with Controlled Microstructure by Cationic Ring Opening Polymerization." Polymers 13, no. 4 (2021): 651. http://dx.doi.org/10.3390/polym13040651.

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Lignin-based polyols (LBPs) with controlled microstructure were obtained by cationic ring opening polymerization (CROP) of oxiranes in an organosolv lignin (OL) tetrahydrofuran (THF) solution. The control on the microstructure and consequently on the properties of the LBPs such as hydroxyl number, average molecular weight, melting, crystallization and decomposition temperatures, are crucial to determine the performance and application of the derived-products. The influence of key parameters, for example, molar ratio between the oxirane and the hydroxyl groups content in OLO, initial OL concent

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14

Schweikl, H., G. Schmalz, and W. Weinmann. "The Induction of Gene Mutations and Micronuclei by Oxiranes and Siloranes in Mammalian Cells in vitro." Journal of Dental Research 83, no. 1 (2004): 17–21. http://dx.doi.org/10.1177/154405910408300104.

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Oxiranes and siloranes are candidate molecules for the development of composite materials with low shrinkage. Since some of these molecules are highly reactive, they could lead to adverse biological effects from underlying genetic mechanisms. Therefore, we analyzed the formation of micronuclei (chromosomal aberrations) and the induction of gene mutations (HPRT assay) in mammalian cells. The numbers of micronuclei induced by the oxirane di(cyclohexene-epoxidemethyl)ether (Eth-Ep) at low concentrations (10 μM) were about five-fold higher than controls. The related compound epoxy cyclohexyl methy

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15

Mayer, Sandra F., Harald Mang, Andreas Steinreiber, Robert Saf, and Kurt Faber. "Asymmetric total synthesis of (+)-exo-brevicomin based on enantioconvergent biocatalytic hydrolysis of an alkene-functionalized 2,3-disubstituted epoxide." Canadian Journal of Chemistry 80, no. 4 (2002): 362–69. http://dx.doi.org/10.1139/v02-037.

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A short total asymmetric synthesis of (+)-exo- and ()-endo-brevicomin ((+)-exo-3 and ()-endo-3), which are components of the attracting pheromone system of several bark-beetle species belonging to the genera Dendroctonus and Dryocoetes, was accomplished via a chemoenzymatic protocol. The key step consisted of biocatalytic hydrolysis by bacterial epoxide hydrolases of cis-configured 2,3-disubstituted oxiranes bearing olefinic side chains. This reaction proceeded in an enantioconvergent fashion, by affording a single enantiomeric vic-diol from the rac-epoxide in up to 92% ee and 83% isolated y

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16

Fuentespina, Ruben Pomar, José Angel Garcia de la Cruz, Gabriel Durin, Victor Mamane, Jean-Marc Weibel та Patrick Pale. "Borylation and rearrangement of alkynyloxiranes: a stereospecific route to substituted α-enynes". Beilstein Journal of Organic Chemistry 15 (27 червня 2019): 1416–24. http://dx.doi.org/10.3762/bjoc.15.141.

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1,3-Enynes are important building blocks in organic synthesis and also constitute the key motif in various bioactive natural products and functional materials. However, synthetic approaches to stereodefined substituted 1,3-enynes remain a challenge, as they are limited to Wittig and cross-coupling reactions. Herein, stereodefined 1,3-enynes, including tetrasubstituted ones, were straightforwardly synthesized from cis or trans-alkynylated oxiranes in good to excellent yields by a one-pot cascade process. The procedure relies on oxirane deprotonation, borylation and a stereospecific rearrangemen

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17

Shen, Chuang, Xiang Guo, Jun Yu, et al. "Synthesis of 2-(phenoxymethyl)oxirane derivatives through unexpected rearrangement of oxiran-2-ylmethyl benzenesulfonates." Synthetic Communications 47, no. 4 (2017): 273–78. http://dx.doi.org/10.1080/00397911.2016.1258579.

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18

Nugrahani, Ratni Ariatmi, Flora Elvistia Firdaus, Yeti Widyawati, Hana Firginia, and Riris Purnama. "Kinetika reaksi hidroksilasi epoksi minyak jarak pagar menggunakan katalis bentonit." Jurnal Teknik Kimia Indonesia 12, no. 2 (2018): 257. http://dx.doi.org/10.5614/jtki.2013.12.2.5.

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Hydroxylation kinetics of jatropha oil epoxy using bentonite catalyst. Based on chemical properties such as fatty acid compositions and iodium value, jatropha curcas oil can potentially be applied as lubricant. Unsaturation of this oil decreases its oxidative stability. Improvement of this property may be done by chemical modification involving epoxidation and oxirane ring opening with bentonite catalyst, forming polyol by hydroxylation. The purpose of this research is to characterize the products and kinetics of the oxirane ring opening reaction. The results of chemical analysis by titration

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19

Barmaki, Mohammad, Gulgaz Valiyeva, Abel A. Maharramovm, and Mirze M. Allaverdiyev. "Synthesis of 2,3-Dihydro-6-methyl-2-thiopyrimidin-4(1H)-one (6-Methylthiouracil) Derivatives and Their Reactions." Journal of Chemistry 2013 (2013): 1–6. http://dx.doi.org/10.1155/2013/176213.

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The synthesis and characterization of 2,3-dihydro-6-methyl-2-thioxopyrimidin-(1H)-one (I) and some of its derivatives has been performed in our lab. Ring-closing cyclization, as a result of the condensation of ethyl-3-oxobutanoate with thiourea in KOH in an ethanol medium produced 2,3-dihydro-6-methy -2-thioxopyrimidin-(1H)-one (I). The reaction of compound (I) with 2- chloroacetic acid in an alkaline KOH solution produced the carboxylate derivative, 2-(2,6-dihydro-4-methyl-6-oxopyrimidin-2-yl-thio)ethanoic acid (II). The reaction of the resulted derivative of carboxylate (II) with the salt of

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20

Florio, Saverio, Vito Capriati, and Serena Di Martino. "An efficient synthesis of oxiranyl oxazolines and elaboration to acyl oxiranes." Tetrahedron Letters 39, no. 31 (1998): 5639–42. http://dx.doi.org/10.1016/s0040-4039(98)01096-x.

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21

Mali, Suraj N., Sudhir Sawant, Hemchandra K. Chaudhari, and Mustapha C. Mandewale. "In Silico Appraisal, Synthesis, Antibacterial Screening and DNA Cleavage for 1,2,5-thiadiazole Derivative." Current Computer-Aided Drug Design 15, no. 5 (2019): 445–55. http://dx.doi.org/10.2174/1573409915666190206142756.

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Background: : Thiadiazole not only acts as “hydrogen binding domain” and “two-electron donor system” but also as constrained pharmacophore. Methods:: The maleate salt of 2-((2-hydroxy-3-((4-morpholino-1, 2,5-thiadiazol-3-yl) oxy) propyl) amino)- 2-methylpropan-1-ol (TML-Hydroxy)(4) has been synthesized. This methodology involves preparation of 4-morpholino-1, 2,5-thiadiazol-3-ol by hydroxylation of 4-(4-chloro-1, 2,5-thiadiazol-3-yl) morpholine followed by condensation with 2-(chloromethyl) oxirane to afford 4-(4-(oxiran-2-ylmethoxy)-1,2,5-thiadiazol- 3-yl) morpholine. Oxirane ring of this com

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22

Solomek, Tomas, Peter Stacko, Aneesh Tazhe Veetil, Tomas Pospisil, and Petr Klan. "Photoenolization-Induced Oxirane Ring Opening in 2,5-Dimethylbenzoyl Oxiranes To Form Pharmaceutically Promising Indanone Derivatives." Journal of Organic Chemistry 75, no. 21 (2010): 7300–7309. http://dx.doi.org/10.1021/jo101515a.

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23

Klys, Arkadiusz, Wojciech Czardybon, John Warkentin, and Nick Henry Werstiuk. "Synthesis and thermolysis of a spiro-fused oxadiazoline Evidence for sequential formation of carbene and oxirane intermediates, and for oxirane dimerization." Canadian Journal of Chemistry 82, no. 12 (2004): 1769–73. http://dx.doi.org/10.1139/v04-158.

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The spiro-fused oxadiazoline, 3,4-diaza-2,2-dimethyl-1,6,10-trioxaspiro[4.5]dec-3-ene, when thermolysed in a sealed tube in benzene-d6 at 110 °C, afforded acetone and an apparent oxirane intermediate (2,2-dimethyl-1,4,8-trioxaspiro[2.5]octane) that could not be isolated. Attempts to isolate the oxirane gave a dimer (8,8,11,11-tetramethyl-1,5,7,10,12,16-hexaoxadispiro[5.2.5.2]hexadecane) as the major product. The oxirane is thermally stable at 110 °C but it is very sensitive to water, as indicated by its gradual disappearance after the tube was opened. The dimer of the oxirane is believed to fo

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24

Swinarew, Andrzej, Beata Swinarew, Jadwiga Gabor, et al. "New Kind of Polymer Materials Based on Selected Complexing Star-Shaped Polyethers." Polymers 11, no. 10 (2019): 1554. http://dx.doi.org/10.3390/polym11101554.

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In today’s analytical trends, there is an ever-increasing importance of polymeric materials for low molecular weight compounds including amines and drugs because they can act as carriers or capture amines or drugs. The use of this type of materials will allow the development of modern materials for the chromatographic column beds and the substrates of selective sensors. Moreover, these kinds of materials could be used as a drug carrier. Therefore, the aim of this study is presenting the synthesis and complexing properties of star-shaped oxiranes as a new sensor for the selective complexation o

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FLORIO, S., V. CAPRIATI, and S. DI MARTINO. "ChemInform Abstract: An Efficient Synthesis of Oxiranyl Oxazolines and Elaboration to Acyl Oxiranes." ChemInform 29, no. 43 (2010): no. http://dx.doi.org/10.1002/chin.199843145.

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26

Pinto, Amaro, and Bernardo. "Experimental Study on the Surface Properties of Nanoalumina-Filled Epoxy Resin Nanocomposites." Applied Sciences 10, no. 3 (2020): 733. http://dx.doi.org/10.3390/app10030733.

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This article presents an experimental study on the surface properties of epoxy resin nanocomposites (EPNCs) manufactured with a thermosetting epoxy resin (EP)–bisphenol A diglycidyl ether (BADGE)–2-[[4-[2-[4-(Oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenoxy]methyl]oxirane) and filled with alumina nanoparticles (NPs). The NPs consist of pretreated (with a silane agent) alpha alumina with irregular shapes and a 100 nm maximum size. Three weight fractions of NPs were studied: 1, 3, and 5 wt. (%). Two different epoxy (EP) resins were manufactured, one cured and postcured with bis (4-aminophenyl) meth

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Dawid, Malgorzata, Paul C. Venneri, and John Warkentin. "Epoxide of a ketene acetal. The first 2,2-dialkoxyoxirane to be isolated." Canadian Journal of Chemistry 79, no. 2 (2001): 110–13. http://dx.doi.org/10.1139/v00-202.

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Dimethoxycarbene, generated at 110°C in benzene by thermolysis of 2,2-dimethoxy-5,5-dimethyl-Δ3-1,3,4-oxadiazoline, reacted with cyclohexanone to afford 2,2-dimethoxyspiro[2.5]-1-oxaoctane. It is the first oxirane of a ketene acetal that could be isolated and characterized by 1H NMR-, 13C NMR-, and IR spectroscopy. The identical oxirane might be expected from conrotatory cyclization of the appropriate carbonyl ylide. That ylide was generated under identical conditions by thermolysis of an oxadiazoline precursor (3,4-diaza-2,2-dimethoxy-1-oxaspiro[4.5]dec-3-ene) (14). The ylide could either cyc

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28

Firdaus, Flora Elvistia. "OPTIMASI PROSES PRODUKSI EPOKSIDA RAMI (Linum Usitatissimum) TERHADAP KARAKTERISASI BILANGAN OKSIRAN." JRSKT - Jurnal Riset Sains dan Kimia Terapan 1, no. 2 (2011): 82. http://dx.doi.org/10.21009/jrskt.012.03.

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Conversion of edible oil; linseed oil (Linum Usitatissimum) to epoxide can be existed by using peracetic acid which can be applied by in situ method. The aim of the research was to identify the effect of temperature and catalyst to the oxirane number of linseed epoxide. The ratio of acetic acid to peroxide were 1/3,66; 1/3,74; 1/3,89; and 1/3,97 (mol/mol); with designated temperature of 600C and 700C, and amount of catalyst were 1,3; 1,5; 1,6; 1,7; and 2,0% (v/v). The highest oxirane number were achieved by the value of 5,8 % mgr KOH/gr with optimized ratio of reactants was1/3,74 and the amoun

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Savithri, M. P., P. S. Yuvaraj, B. S. R. Reddy, R. Raja, and A. SubbiahPandi. "Crystal structure of methyl 1-methyl-2-oxospiro[indoline-3,2′-oxirane]-3′-carboxylate." Acta Crystallographica Section E Crystallographic Communications 71, no. 5 (2015): o274—o275. http://dx.doi.org/10.1107/s2056989015006398.

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In the title compound, C12H11NO4, the dihedral angle between the indole ring system (r.m.s. deviation = 0.019 Å) and the oxirane ring is 88.8 (2)°. The oxirane O atom and the bridging ester O atom are in an approximate syn conformation [O—C—C—O = −25.4 (3)°] In the crystal, inversion dimers linked by pair of C—H...O hydrogen bonds generateR22(8) loops, where the C—H donor group forms part of the oxirane ring. A second C—H...O interaction arising from one of the C—H groups of the benzene ring links the dimers into [001] double chains.

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30

Musik, Marlena, Eugeniusz Milchert, and Kornelia Malarczyk-Matusiak. "Technological Parameters of Epoxidation of Sesame Oil with Performic Acid." Polish Journal of Chemical Technology 20, no. 3 (2018): 53–59. http://dx.doi.org/10.2478/pjct-2018-0038.

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Abstract The course of epoxidation of sesame oil (SO) with performic acid formed „in situ” by the reaction of 30 wt% hydrogen peroxide and formic acid in the presence of sulfuric acid(VI) as a catalyst was studied. The most advantageous of the technological independent parameters of epoxidation are as follows: temperature 80°C, H2O2/ C=C 3.5:1, HCOOH/C=C 0.8:1, amount of catalyst as H2SO4/(H2O2+HCOOH) 1 wt%, stirring speed at least 700 rpm, reaction time 6 h. The iodine number (IN), epoxy number (EN), a relative conversion to oxirane (RCO) and oxirane oxygen content (EOe) were determined every

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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 (2017): 5977–88. http://dx.doi.org/10.24297/jac.v13i12.6152.

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Oxirane ring containing the carboxylic group in the Î±,Î²-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 Î±-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

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Chen, Chien-Han, Chia-Min Lin, Tzong-Yuan Juang, Mahdi M. Abu-Omar, and Ching-Hsuan Lin. "The reaction of activated esters with epoxides for self-curable, highly flexible, A2B2- and A3B3-type epoxy compounds." Polymer Chemistry 10, no. 29 (2019): 3983–95. http://dx.doi.org/10.1039/c9py00377k.

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To achieve high-T<sub>g</sub> and low-dissipation epoxy thermosets, bis(2-methoxy-4-(oxiran-2-ylmethyl)phenyl)isophthalate (2) and tris(2-methoxy-4-(oxiran-2-ylmethyl)phenyl)benzene-1,3,5-tricarboxylate (3) were prepared.

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Jalil, Mohd Jumain, Noorfazlida Mohamed, Siti Khatijah Jamaludin, Ayub M. Som, and Ahmad Rafizan Mohamad Daud. "Epoxidation of Palm Kernel Oil-Based Crude Oleic Acid." Advanced Materials Research 906 (April 2014): 125–30. http://dx.doi.org/10.4028/www.scientific.net/amr.906.125.

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Most vegetable oils have high content of unsaturated bond and can be converted into epoxidized fatty acids. These days, epoxidized vegetable oils are great concern as they are obtained from sustainable, renewable natural resources and are environmental friendly. The epoxidation of palm oleic acid was carried out by using in situ generated performic acid (HCOOOH) to produce epoxidized oleic acid. The degree of temperature, the molar ratio of formic acid or hydrogen peroxide and types of catalyst was considered. Epoxidation results were based on complete conversion oxirane, rate of epoxidation a

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34

McDowell, Sean A. C., and Satoria J. Maynard. "A computational study of model beryllium-bonded complexes of oxirane and F-substituted oxiranes with BeX2 (X=H, Cl)." Chemical Physics Letters 630 (June 2015): 91–95. http://dx.doi.org/10.1016/j.cplett.2015.04.046.

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Schwab, John M., and Chorng-Kei Ho. "Chirally-labelled oxirane." Journal of the Chemical Society, Chemical Communications, no. 11 (1986): 872. http://dx.doi.org/10.1039/c39860000872.

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36

Salzman, W. R., and P. L. Polavarapu. "Calculated rotational strengths and dissymmetry factors for rotational transitions of the chiral deuterated oxiranes, methyl- and dimethyl-oxirane, and methylthiirane." Chemical Physics Letters 179, no. 1-2 (1991): 1–8. http://dx.doi.org/10.1016/0009-2614(91)90282-e.

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Yutilova, Kseniia, Yuliia Bespal’ko, and Elena Shved. "A Computational Study of 2-(chloromethyl)oxirane Ring Opening by Bromide and Acetate Anions Considering Electrophilic Activation with Cations of Alkali Metals." Croatica chemica acta 92, no. 3 (2019): 357–67. http://dx.doi.org/10.5562/cca3505.

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Ring opening of 2-(chloromethyl)oxirane via the nucleophilic substitution with bromide and acetate anions was investigated using density functional theory (DFT) calculations. It was shown that the geometry of the transition states and the activation parameters of the reactions correspond to those of SN2-like mechanism. The nature of localized transition states was analyzed using More O’Ferrall – Jencks plots. The quantum chemical simulations of the potential energy surface for the ring-opening reaction of oxirane by nucleophiles confirmed the theoretical assumptions about the favored path of i

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Tuzimski, Tomasz, Szymon Szubartowski, Renata Gadzała-Kopciuch, et al. "Comparison of DAD and FLD Detection for Identification of Selected Bisphenols in Human Breast Milk Samples and Their Quantitative Analysis by LC-MS/MS." Journal of AOAC INTERNATIONAL 103, no. 4 (2020): 1029–42. http://dx.doi.org/10.1093/jaoacint/qsaa027.

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Abstract Background Determination of bisphenols released from packaging material is undoubtedly a difficult and tricky task, requiring the chemical analyst to develop an individual approach to obtain reliable analytical information. Objective QuECHERS (Quick, Easy, Cheap, Effective, Rugged, and Safe)/dispersive solid-phase extraction (d-SPE) technique and high performance liquid chromatography (HPLC) coupled with modern detection techniques such as diode-array detector (DAD), ﬂuorescence detector (FLD) or tandem mass spectrometry (MS/MS) for the determination of bisphenols such as bisphenol A

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Bakhtin, Stanislav, Elena Shved, Yuliia Bespal'ko, and Yuliia Stepanova. "Behaviour Modelling of Organic Bases in the Oxyalkylation Reaction of Proton-Containing Nucleophiles." Progress in Reaction Kinetics and Mechanism 43, no. 2 (2018): 121–35. http://dx.doi.org/10.3184/146867818x15161889114501.

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The mechanism of action of nucleophilic and non-nucleophilic bases in the system “acetic acid (HOAc) – epichlorohydrin (ECH) – R3X (R = alkyl, X = N, P)” has been studied. The observed orders of the reaction with respect to the components were found. It has been proved that the catalytic activity of the starting bases is determined by their nucleophilicity, rather than basicity. It is shown that the crucial stage of the reaction is the quaternisation of the starting base with the formation of a reactive intermediate, the acetate anion. Monitoring of possible paths of oxirane ring-opening by th

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Sammer, Ulrike F., Beate Völksch, Ute Möllmann, et al. "2-Amino-3-(Oxirane-2,3-Dicarboxamido)-Propanoyl-Valine, an Effective Peptide Antibiotic from the Epiphyte Pantoea agglomerans 48b/90." Applied and Environmental Microbiology 75, no. 24 (2009): 7710–17. http://dx.doi.org/10.1128/aem.01244-09.

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ABSTRACT The epiphyte Pantoea agglomerans 48b/90, which has been isolated from soybean leaves, belongs to the Enterobacteriaceae, as does the plant pathogen Erwinia amylovora, which causes fire blight on rosaceous plants such as apples and leads to severe economic losses. Since P. agglomerans efficiently antagonizes phytopathogenic bacteria, the P. agglomerans strain C9-1 is used as a biocontrol agent (BlightBan C9-1). Here we describe the bioassay-guided isolation of a peptide antibiotic that is highly active against the plant pathogen E. amylovora and pathovars of Pseudomonas syringae, and w

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Hess, B. Andes. "On the Concerted Ring Opening of Protonated Squalene Oxide and A-Ring Formation in the Biosynthesis of Lanosterol." Collection of Czechoslovak Chemical Communications 68, no. 1 (2003): 202–10. http://dx.doi.org/10.1135/cccc20030202.

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Density functional calculations were performed on a model system of squalene oxide to study the mechanism of the formation of ring A in the biosynthesis of lanosterol from squalene. When (2Z)-6,7-epoxy-3,7-dimethyloct-2-ene was protonated, it was calculated to undergo a very facile ring opening of the oxirane in concert with the formation of the six-membered ring of the 4-(hydroxymethyl)-1,2,3,3-tetramethy1cyclohexyl cation. A study of the reaction pathway (IRC) indicates a very early transition structure in which the carbon- carbon double bond participates anchimerically in the ring-opening o

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Freedman, Teresa B., Kevin M. Spencer, N. Ragunathan, Laurence A. Nafie, Jeffrey A. Moore, and John M. Schwab. "Vibrational circular dichroism of (S,S)-[2,3-2H2]oxirane in the gas phase and in solution." Canadian Journal of Chemistry 69, no. 11 (1991): 1619–29. http://dx.doi.org/10.1139/v91-237.

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Vibrational circular dichroism (VCD) spectra of an exceptionally simple chiral three-membered ring molecule, (S,S)-[2,3-2H2]oxirane, have been obtained for samples in the gas phase and in C2Cl4 and CS2 solution. The VCD band contours for the gas phase samples of this molecule with C2 symmetry follow those of the absorption spectra, with the modes of A symmetry species giving rise to bands with two sharp Q-branch maxima on either side of a distinct minimum, and the modes of B symmetry species giving rise to bands with a strong central Q-branch. The signs and relative intensities of the VCD band

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Liu, Bing, Enxiang Wei, Shaoxia Lin, Baozhong Zhao, and Fushun Liang. "Synthesis of spiro[isoquinolinone-4,2′-oxiranes] and isoindolinones via a multicomponent reaction of 2-acetyl-oxirane-2-carboxamides, arylaldehydes and malononitrile." Chemical Communications 50, no. 53 (2014): 6995. http://dx.doi.org/10.1039/c4cc02141j.

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44

Mohamed, A. A., S. Hussain, M. S. Alamri, M. A. Ibraheem, and Akram A. Abdo Qasem. "Amidolysis of Oxirane: Effect of Protein Type, Oils, and ZnCl2 on the Rheological Properties of Cross-Linked Protein and Oxirane." International Journal of Polymer Science 2018 (2018): 1–11. http://dx.doi.org/10.1155/2018/9670565.

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Amidolysis of oxirane group of epoxidized sesame, sunflower, and cottonseed oils was achieved by reaction with primary amide of millet and gluten proteins. Gluten is a coproduct of wheat starch industry and available commercially. Millet is a major part of the staple food of the semiarid region of the tropics. Gluten is a mixture of glutenins and gliadins rich in glutamine residues; however, millet is rich in glutamine and leucine. We have taken advantage of the available primary amide of glutamine for cross-linking with the oxirane of sunflower, sesame, and cottonseed oils under controlled co

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He, Xi Pu, Xia Deng, Seng Sheng Wang, Jun Xiong, and Yu Xiang Gu. "Catalytic Epoxidation of Soybean Oil Methyl Esters." Advanced Materials Research 396-398 (November 2011): 833–36. http://dx.doi.org/10.4028/www.scientific.net/amr.396-398.833.

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The plant oil-based epoxy materials are considered as environment-friendly, biodegradable, renewable raw materials, potentially replacing petrochemical-based epoxy materials in many fields. Soybean oil methyl esters (SOME) were epoxidized with Prileshajev and Chemo-enzymatic reactions. The highest epoxy oxirane achieved by Prileshajev epoxidation was only 4.42%, however, it could reach 5.63% by chemo-enzymatic epoxidation. The stability of oxirane by chemo-enzymatic epoxidation was better than that by Prileshajev epoxidation. The results showed that the chemo-enzymatic method was extremely eff

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Lv, Jia, Hong Chang, Yu Wang, et al. "Fluorination on polyethylenimine allows efficient 2D and 3D cell culture gene delivery." Journal of Materials Chemistry B 3, no. 4 (2015): 642–50. http://dx.doi.org/10.1039/c4tb01447b.

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Jing, Ying, and Xiaojun Tan. "A theoretical study on the mechanism of the reaction between azacyclopropenylidene and oxirane." Journal of the Serbian Chemical Society 80, no. 1 (2015): 53–62. http://dx.doi.org/10.2298/jsc140509056j.

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The reaction mechanism between azacyclopropenylidene and oxirane has been systematically investigated employing the second-order M?ller-Plesset perturbation theory (MP2) method to better understand the azacyclopropenylidene reactivity with three-membered ring compound oxirane. Geometry optimization, vibrational analysis, and energy property for the involved stationary points on the potential energy surface have been calculated. Energies of all the species are also further corrected by CCSD(T)/6-311+G* single-point calculations. Our calculational results show that there are two possible reactio

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Kantee, Jutamas, and Somjai Kajorncheappunngam. "Characterization of Epoxidized Rubber Seed Oil." Key Engineering Materials 728 (January 2017): 295–300. http://dx.doi.org/10.4028/www.scientific.net/kem.728.295.

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Epoxidation of rubber seed oil was carried out using a peroxyacid generated in situ from glacial acetic acid and hydrogen peroxide to produce epoxidized rubber seed oil. The maximum relative conversion to oxirane of 88 % could be obtained at 60 °C after a reaction time of 7 hours. The presence of oxirane ring of epoxidized rubber seed oil was confirmed by fourier transform infrared spectrometer (FT-IR) and proton nuclear magnetic resonance (1H NMR) spectra analysis which displayed a disappearance of double bonds peak in rubber seed oil and an existing of epoxide ring peak in epoxidized rubber

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Ha, Hyun-Joon. "Preface to “Aziridine Chemistry”." Molecules 26, no. 6 (2021): 1525. http://dx.doi.org/10.3390/molecules26061525.

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Mandzhulo, Aleksandr, Iryna Vashchenko, Andrii Gerasov, et al. "Selective synthesis of N-protected exo-spiro[oxirane-3,2′-tropanes]." Organic Chemistry Frontiers 6, no. 10 (2019): 1692–97. http://dx.doi.org/10.1039/c9qo00377k.

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