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Journal articles on the topic 'Oxirene'

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Published: 4 June 2021

Last updated: 4 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

Lewars, E. "Benzooxirene, naphthooxirenes, and anthraceneoxirenes: the stabilization of the oxirene system by bond fixation in acenes. A comparison of ab initio and DFT in the investigation of annelated oxirenes." Canadian Journal of Chemistry 78, no. 2 (2000): 297–306. http://dx.doi.org/10.1139/v00-004.

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The effect on the stabilities of benzoannelated oxirenes (oxacyclopropenes) of variations in the C-C bond electron density (as measured by Löwdin bond order) was studied computationally. Benzo[b]oxirene (4ox), naphtho[2,3-b]oxirene (5ox), naphtho[1,2-b]oxirene (6ox), anthro[2,3-b]oxirene (7ox), and anthro[1,2-b]oxirene (8ox) were investigated using the DFT pBP/DN* method as implemented in the program Spartan. This method was chosen because with 4ox it gave results similar to those from the much slower QCISD(T)/6-31G*//MP2(full)/6-31G* and MP4SDTQ/6-31G*//MP2(full)/6-31G* methods. The calculate

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3

Delamere, C., C. Jakins, and E. Lewars. "On the generation of oxirene and dimethyloxirene by retro-DielsAlder reactions, and reactions of dimethyloxirene: a computational study." Canadian Journal of Chemistry 80, no. 1 (2002): 94–105. http://dx.doi.org/10.1139/v01-194.

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The isomerization of oxirene (oxacyclopropene) (1) to ketene, dimethyloxirene (7) to dimethylketene via the oxo carbene ("ketocarbene"), and the retro-DielsAlder extrusion of oxirene and dimethyloxirene from their formal adducts (9 and 24, respectively) with benzene were studied computationally. All species were optimized at the MP2(fc)/631G(df,p) level; the species involving 1 were also subjected to MP2(fc)/631G(df,p) frequency and single-point CCSD(T)/631G(df,p) calculations. At the CCSD(T)/631G(df,p)//MP2(fc)/631G(df,p) level 1 isomerized to ketene in one step with a barrier of 2.8 kJ

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4

Rühl, Wolfgang, Friedrich Bölsing, Edgar Hofer, Dietrich Speer, and Martin Jansen. "Das Ketocarben-Oxiren-Gleichgewicht unter einem präparativen Aspekt≠ / The Oxiren-Oxo Carbene Interconversion from a More Preparative Point of View≠." Zeitschrift für Naturforschung B 41, no. 6 (1986): 772–75. http://dx.doi.org/10.1515/znb-1986-0616.

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Abstract The photochemical decomposition of α-diazoketone 1 in toluene gives rise to the formation of the well known keto carbene-oxirene equilibrium from which not only the product of the Wolff rearrangem ent can be derived but also the com pounds 5, 6 and 7 which are formed directly via the corresponding keto carbenes A and B respectively. Formation of the azulene 6 is unexpected in this context, it's structure could be revealed by X-ray analysis. The results may be regarded as an additional contribution to the mechanism of the Wolff rearrangement, but what is more, they could serve as a mod

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5

Zeller, K., A. Blocher, and P. Haiss. "Oxirene Participation in the Photochemical Wolff Rearrangementa." Mini-Reviews in Organic Chemistry 1, no. 3 (2004): 291–308. http://dx.doi.org/10.2174/1570193043403181.

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6

Vacek, George, John Morrison Galbraith, Yukio Yamaguchi, et al. "Oxirene: To Be or Not To Be?" Journal of Physical Chemistry 98, no. 35 (1994): 8660–65. http://dx.doi.org/10.1021/j100086a013.

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7

Haiss, Peter, та Klaus-Peter Zeller. "Teilweise Sauerstoff-Wanderung in der photochemischen Wolff-Umlagerung – α-Oxocarben-Oxiren-Isomerisierung oder intermolekularer Mechanismus?" Zeitschrift für Naturforschung B 58, № 6 (2003): 595–605. http://dx.doi.org/10.1515/znb-2003-0616.

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Crossover experiments between isotopomeric species of 2-diazo-1-oxo-1-phenylethane (18O, 13C, D) establish beyond doubt that the oxygen migration accompanying the photochemical Wolff rearrangement is not the result of intermolecular processes. This is in agreement with a carbenecarbene rearrangement via an intermediate oxirene in competition to the rearrangement into a ketene, as reason for the partial oxygen migration in the Wolff rearrangement products.

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8

Tanigaki, K., and T. W. Ebbesen. "Dynamics of the Wolff rearrangement: spectroscopic evidence of oxirene intermediate." Journal of the American Chemical Society 109, no. 19 (1987): 5883–84. http://dx.doi.org/10.1021/ja00253a069.

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9

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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10

Wilson, Philip J., and David J. Tozer. "A Kohn–Sham study of the oxirene–ketene potential energy surface." Chemical Physics Letters 352, no. 5-6 (2002): 540–44. http://dx.doi.org/10.1016/s0009-2614(01)01496-8.

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11

Hop, C. E. C. A., J. L. Holmes, and J. K. Terlouw. "The oxirene radical cation and its neutralization in the gas phase." Journal of the American Chemical Society 111, no. 2 (1989): 441–45. http://dx.doi.org/10.1021/ja00184a005.

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12

Vacek, George, Brenda Thies Colegrove, and Henry F. Schaefer. "Does oxirene exist? A theoretical inquiry involving the coupled-cluster method." Chemical Physics Letters 177, no. 4-5 (1991): 468–70. http://dx.doi.org/10.1016/0009-2614(91)85085-b.

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13

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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14

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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15

Scott, Anthony P., Ross H. Nobes, Henry F. Schaefer, and Leo Radom. "The Wolff Rearrangement: The Relevant Portion of the Oxirene-Ketene Potential Energy Hypersurface." Journal of the American Chemical Society 116, no. 22 (1994): 10159–64. http://dx.doi.org/10.1021/ja00101a039.

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16

BLOCHER, A., and K. P. ZELLER. "ChemInform Abstract: Photolysis of Naphth(2,3-d)-1,2,3-oxadiazole - A Contribution to the Oxirene Problem." ChemInform 25, no. 29 (2010): no. http://dx.doi.org/10.1002/chin.199429071.

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17

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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18

Mawhinney, Robert C., and John D. Goddard. "Assessment of density functional theory for the prediction of the nature of the oxirene stationary point." Journal of Molecular Structure: THEOCHEM 629, no. 1-3 (2003): 263–70. http://dx.doi.org/10.1016/s0166-1280(03)00198-2.

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19

Lewars, Errol. "Push-pull substitution evidently does not stabilize the oxirene system: an AM1 and ab initio study." Journal of Molecular Structure: THEOCHEM 391, no. 1-2 (1997): 39–50. http://dx.doi.org/10.1016/s0166-1280(96)04798-7.

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20

TORRES, M., R. K. GOSAVI, E. M. LOWN та ін. "ChemInform Abstract: The Wolff Rearrangement of α-Diazo Ketones: The Role of Oxirene and Its Isomers". ChemInform 24, № 23 (2010): no. http://dx.doi.org/10.1002/chin.199323318.

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21

Lewars, E. "ChemInform Abstract: Benzooxirene, Naphthooxirenes, and Anthraceneoxirenes: The Stabilization of the Oxirene System by Bond Fixation in Acenes. A Comparison of ab initio and DFT in the Investigation of Anellated Oxirenes." ChemInform 31, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.200024031.

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22

Anusha, Chakkittakandiyil, Susmita De, and Pattiyil Parameswaran. "Ring contraction of metallabenzooxirene to metal carbonyl complexes – a comparative study with the Wolff rearrangement of oxirene and benzooxirene." Dalton Trans. 46, no. 40 (2017): 13974–82. http://dx.doi.org/10.1039/c7dt02911j.

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23

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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24

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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25

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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26

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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27

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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28

van Baar, Ben L. M., Nikolaus Heinrich, Wolfram Koch, Ron Postma, Johan K. Terlouw, and Helmut Schwarz. "CO2 Elimination from Vinylene Carbonate Radical Anions and Charge Reversal in C2H2O⊙⊖: Reactions Involving the Radical Anion and Cation of Oxirene?" Angewandte Chemie International Edition in English 26, no. 2 (1987): 140–42. http://dx.doi.org/10.1002/anie.198701401.

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29

Pinkerton, A. Alan, Anthony Martin, Alan P. Marchand, and Arokiasamy Devasagayaraj. "Intermolecular [2+2] photocyclization of ethyl 5-oxo-1a,2,5,5a,6,6a-hexahydro-2,6-methano-2aH-indeno-[5,6-b]oxirene-2a-carboxylate." Journal of Chemical Crystallography 27, no. 12 (1997): 701–5. http://dx.doi.org/10.1007/bf02576549.

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30

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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31

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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32

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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33

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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34

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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35

Abu-Shqara, Elias, and Jochanan Blum. "The syntheses of 4b,5a-dihydrodibenz[3,4:5,6]anthra[1,2-b]oxirene and 4b,5a-dihydro-5H-dibenz[3,4:5,6]anthra[1,2-b]azirine." Journal of Heterocyclic Chemistry 28, no. 2 (1991): 473–75. http://dx.doi.org/10.1002/jhet.5570280251.

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36

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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37

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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38

ABU-SHQARA, E., and J. BLUM. "ChemInform Abstract: Syntheses of 4b,5a-Dihydrodibenz(3,4:5,6)anthra(1,2-b)oxirene and 4b,5a-Dihydro-5H-dibenz(3,4:5,6)anthra(1,2-b)azirine." ChemInform 22, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.199130154.

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39

Girard, Yvan, and Patrick Chaquin. "Addition Reactions of1D and3P Atomic Oxygen with Acetylene. Potential Energy Surfaces and Stability of the Primary Products. Is Oxirene Only a Triplet Molecule? A Theoretical Study." Journal of Physical Chemistry A 107, no. 48 (2003): 10462–70. http://dx.doi.org/10.1021/jp021962q.

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40

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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41

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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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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43

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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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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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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Chen, Hao, John Shockcor, Weiqi Chen, Robert Espina, Liang-Shang Gan, and A. E. Mutlib. "Delineating Novel Metabolic Pathways of DPC 963, a Non-Nucleoside Reverse Transcriptase Inhibitor, in Rats. Characterization of Glutathione Conjugates of Postulated Oxirene and Benzoquinone Imine Intermediates by LC/MS and LC/NMR." Chemical Research in Toxicology 15, no. 3 (2002): 388–99. http://dx.doi.org/10.1021/tx010153f.

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Hofstraat, R. G., J. W. Scheeren, R. P. F. Kanters, J. M. M. Smits, and Paul T. Beurskens. "Preparation and crystal and molecular structure of erythro(1a?,2?,4a?)-2-hydroxy-4a-methyl-1a,2,4,4a,5,6,7, 8-octahydro-3H-naphth-[1,8a-b]-oxirene-2?-(2?-methyl)-acetic acid methyl ester, C15H24O4." Journal of Crystallographic and Spectroscopic Research 18, no. 5 (1988): 641–45. http://dx.doi.org/10.1007/bf01161158.

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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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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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