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Journal articles on the topic 'Nucleophilic opening'

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1

Talukdar, Ranadeep. "Synthetically Important Ring-Opening Acylations of Alkoxybenzenes." Synthesis 52, no. 24 (2020): 3764–80. http://dx.doi.org/10.1055/s-0040-1707255.

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AbstractCyclic ketones, anhydrides, lactams and lactones are a particular class of molecules that are often used in synthesis, wherein their electrophilic properties are leveraged to enable facile Friedel–Crafts ring openings through nucleophilic attack at the carbonyl sp2 centre. The use of electron-rich alkoxybenzenes as nucleophiles has also become important since the discovery of the Friedel–Crafts reaction. As a result, various isomeric alkoxybenzenes are used for preparing starting materials in target-oriented syntheses. This review covers the instances of different alkoxybenzenes that a
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2

Rani, Poonam, and Rajendra Srivastava. "Nucleophilic addition of amines, alcohols, and thiophenol with epoxide/olefin using highly efficient zirconium metal organic framework heterogeneous catalyst." RSC Advances 5, no. 36 (2015): 28270–80. http://dx.doi.org/10.1039/c5ra00921a.

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3

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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4

Carramiñana, Victor, Ana M. Ochoa de Retana, Francisco Palacios та Jesús M. de los Santos. "Synthesis of α-Aminophosphonic Acid Derivatives Through the Addition of O- and S-Nucleophiles to 2H-Azirines and Their Antiproliferative Effect on A549 Human Lung Adenocarcinoma Cells". Molecules 25, № 15 (2020): 3332. http://dx.doi.org/10.3390/molecules25153332.

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This work reports a straightforward regioselective synthetic methodology to prepare α-aminophosphine oxides and phosphonates through the addition of oxygen and sulfur nucleophiles to the C–N double bond of 2H-azirine derivatives. Determined by the nature of the nucleophile, different α-aminophosphorus compounds may be obtained. For instance, aliphatic alcohols such as methanol or ethanol afford α-aminophosphine oxide and phosphonate acetals after N–C3 ring opening of the intermediate aziridine. However, addition of 2,2,2-trifluoroethanol, phenols, substituted benzenthiols or ethanethiol to 2H-
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5

Hu, X. Eric. "Nucleophilic ring opening of aziridines." Tetrahedron 60, no. 12 (2004): 2701–43. http://dx.doi.org/10.1016/j.tet.2004.01.042.

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6

Stamm, Helmut. "Nucleophilic ring opening of aziridines." Journal für praktische Chemie 341, no. 4 (1999): 319–31. http://dx.doi.org/10.1002/(sici)1521-3897(199905)341:4<319::aid-prac319>3.0.co;2-9.

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7

Wei, Lan, and William D. Lubell. "Scope and limitations in the use of N-(PhF)serine-derived cyclic sulfamidates for amino acid synthesis." Canadian Journal of Chemistry 79, no. 1 (2001): 94–104. http://dx.doi.org/10.1139/v00-176.

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Ring-opening of N-(PhF)serine-derived cyclic sulfamidate 17 was achieved with different nucleophiles (β-keto esters, β-keto ketones, dimethyl malonate, nitroethane, sodium azide, imidazole, and potassium thiocyanate) to prepare a variety of amino acid analogs. Two different pathways for ring opening of 17 were elucidated: direct nucleophilic displacement, as well as β-elimination followed by Michael addition. Furthermore, β-keto ester and β-keto ketone products 18k,18m, and 18i were converted to prolines and pyrazole amino acids.Key words: glutamate, amino acid, cyclic sulfamidate, proline.
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8

Zhao, Yu, Zitong Zhou, Man Chen, and Weiguang Yang. "Copper-Catalyzed One-Pot Synthesis of N-Sulfonyl Amidines from Sulfonyl Hydrazine, Terminal Alkynes and Sulfonyl Azides." Molecules 26, no. 12 (2021): 3700. http://dx.doi.org/10.3390/molecules26123700.

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N-Sulfonyl amidines are developed from a Cu-catalyzed three-component reaction from sulfonyl hydrazines, terminal alkynes and sulfonyl azides in toluene at room temperature. Particularly, the intermediate N-sulfonylketenimines was generated via a CuAAC/ring-opening procedure and took a nucleophilic addition with the weak nucleophile sulfonyl hydrazines. In addition, the stability of the product was tested by a HNMR spectrometer.
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9

Raheem, Mohammed Abdul, Michael Edmunds, and William Tam. "Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabenzonorbornadienes." Canadian Journal of Chemistry 92, no. 9 (2014): 888–95. http://dx.doi.org/10.1139/cjc-2014-0217.

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The effect of ethyl and methoxycarbonyl substitution on the C1 position of oxabenzonorbornadienes undergoing palladium-catalyzed nucleophilic ring opening was investigated with a variety of aryl iodide nucleophiles. Electron-withdrawing groups in the C1 position or on the aryl iodide afforded lower yields and led to aromatization of products. The presence of an electron-donating group in either position provided high yields in all cases. Despite variances in electronic nature, all trials produced a single regioisomeric product resulting from addition of the aryl group to the olefin carbon fart
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10

Costero, Ana María, Salvador Gil, Margarita Parra, and Pablo Rodríguez. "Unexplored Nucleophilic Ring Opening of Aziridines." Molecules 15, no. 12 (2010): 9135–44. http://dx.doi.org/10.3390/molecules15129135.

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11

Akhtar, Rabia, Syed Ali Raza Naqvi, Ameer Fawad Zahoor, and Sameera Saleem. "Nucleophilic ring opening reactions of aziridines." Molecular Diversity 22, no. 2 (2018): 447–501. http://dx.doi.org/10.1007/s11030-018-9829-0.

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12

Couty, François, François Durrat, and Gwilherm Evano. "Regioselective Nucleophilic Opening of Azetidinium Ions." Synlett, no. 11 (2005): 1666–70. http://dx.doi.org/10.1055/s-2005-871537.

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13

Gautun, Hanna S. H., and Per H. J. Carlsen. "Nucleophilic ring opening of cyclic sulphamidites." Tetrahedron: Asymmetry 6, no. 7 (1995): 1667–74. http://dx.doi.org/10.1016/0957-4166(95)00211-7.

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14

Schindler, Corinna S, Stefan Diethelm, and Erick M Carreira. "Nucleophilic Opening of Oxabicyclic Ring Systems." Angewandte Chemie International Edition 48, no. 34 (2009): 6296–99. http://dx.doi.org/10.1002/anie.200902046.

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15

Schindler, Corinna S, Stefan Diethelm, and Erick M Carreira. "Nucleophilic Opening of Oxabicyclic Ring Systems." Angewandte Chemie 121, no. 34 (2009): 6414–17. http://dx.doi.org/10.1002/ange.200902046.

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16

Santos, A. Mafalda, M. Fernanda N. N. Carvalho, Adelino M. Galvão, and Armando J. L. Pombeiro. "Reactivity Trends in the Reaction of Alkynes with 3-Oxo-camphorsulfonylimine." Zeitschrift für Naturforschung B 57, no. 6 (2002): 691–98. http://dx.doi.org/10.1515/znb-2002-0616.

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Abstract The regioselective addition of deprotonated alkynes (phenyl-1-propyne, propargyl ether or tetrahydropyran-protected 3-butyn-1-ol) to the imine group was identified as a competitive process to the nucleophilic addition to the keto group of (1S)-3-oxo-camphorsulfonylimine. The selectivity of the process depends on the characteristics of the nucleophile and the reaction conditions. In the case of propargyl ether it was possible to render the imine addition the main process.The structural characterization of compounds 1, 2, 6 by X-ray diffraction analysis show that the C2 - C3 bond become
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17

Concellón, José M., Pablo L. Bernad, and Juan A. Pérez-Andrés. "Nucleophilic ring closure and opening of aminoiodohydrins." Tetrahedron Letters 41, no. 8 (2000): 1231–34. http://dx.doi.org/10.1016/s0040-4039(99)02250-9.

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18

Lautens, Mark, and Pauline Chiu. "Regioselective nucleophilic ring opening of oxabicyclic compounds." Tetrahedron Letters 34, no. 5 (1993): 773–76. http://dx.doi.org/10.1016/0040-4039(93)89008-e.

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19

Talaty, Erach R., and Mashitah M. Yusoff. "Regioselectivity in nucleophilic ring-opening of aziridinones." Chemical Communications, no. 9 (1998): 985–86. http://dx.doi.org/10.1039/a800564h.

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20

Schwaebe, Michael K., and R. Daniel Little. "Organometallic nucleophilic ring-opening of endo peroxides." Tetrahedron Letters 37, no. 37 (1996): 6635–38. http://dx.doi.org/10.1016/s0040-4039(96)01494-3.

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21

Stamm, Helmut. "ChemInform Abstract: Nucleophilic Ring Opening of Aziridines." ChemInform 30, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.199936291.

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22

Axelsson, Oskar, and Dan Peters. "The nucleophilic ring-opening ofN-benzylquinuclidinium bromide." Journal of Heterocyclic Chemistry 34, no. 2 (1997): 461–63. http://dx.doi.org/10.1002/jhet.5570340217.

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23

Chen, Yunwei, Xiang Sun, Ningjie Wu та ін. "Synthetic and theoretical investigation on the one-pot halogenation of β-amino alcohols and nucleophilic ring opening of aziridinium ions". Organic & Biomolecular Chemistry 14, № 3 (2016): 920–39. http://dx.doi.org/10.1039/c5ob01692d.

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24

Lee, Michelle, Jessica R. Lamb, Maria J. Sanford, Anne M. LaPointe та Geoffrey W. Coates. "Nucleophilic ring opening of trans-2,3-disubstituted epoxides to β-amino alcohols with catalyst-controlled regioselectivity". Chemical Communications 54, № 92 (2018): 12998–3001. http://dx.doi.org/10.1039/c8cc07200k.

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25

Grant, PK, LR Hanton, SF Tsai, and TM Yap. "Intramolecular Participation Reactions in Labda-8(17),14-dien-13-ol (Manool) Derivatives." Australian Journal of Chemistry 44, no. 3 (1991): 433. http://dx.doi.org/10.1071/ch9910433.

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Lewis acid treatment of a series of hydroxy epoxides promoted intramolecular nucleophilic epoxide opening to give hydroxy cyclic ethers. The regioselectivity of epoxide opening is controlled by a preference for SN2 attack at the more accessible epoxide carbon, provided this does not involve the formation of a strained ether ring. An intramolecular acetate transfer occurs in order to achieve the regioselective opening.
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26

Deora, Nipa, and Paul R. Carlier. "A computational study of regioselectivity in aluminum hydride ring-opening of cis- and trans-4-t-butyl and 3-methylcyclohexene oxides." Organic & Biomolecular Chemistry 17, no. 37 (2019): 8628–35. http://dx.doi.org/10.1039/c9ob01675a.

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27

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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28

Bhuyan, Jagannath. "Nucleophilic ring-opening of iron(iii)-hydroxy-isoporphyrin." Dalton Transactions 45, no. 6 (2016): 2694–99. http://dx.doi.org/10.1039/c5dt03905c.

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The reactions of iron(iii) hydroxyisoporphyrin, chloro[5-(hydroxy)-5,10,15,20-tetrakis(4-methyl)-5,21H-porphinato]iron(iii) [Fe(4-Me-HTPI)(Cl)]<sup>−</sup>, 1 and chloro[5-(hydroxy)-5,10,15,20-tetrakis(4-methoxy-5,21H-porphinato]iron(iii) [Fe(4-OMe-HTPI)(Cl)]<sup>−</sup>, 2 with different O<sup>−</sup>, N<sup>−</sup> and S<sup>−</sup> nucleophiles have been performed to understand the reactivity of iron isoporphyrins with nucleophiles.
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29

Morozova, Yuliya V., Dmitry V. Yashunsky, Zoya A. Starikova, and Gelii V. Ponomarev. "Chemical transformation of 1,2-oxazinochlorin derivatives: synthesis and X-ray crystal structure of a novel porphyrin-porphyrin dimer with a condensed cyclohexane ring." Journal of Porphyrins and Phthalocyanines 11, no. 01 (2007): 31–41. http://dx.doi.org/10.1142/s1088424607000059.

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Base-assisted ring opening in 1,2-oxazinochlorin derivatives led selectively to the corresponding meso-cyanohydroxychlorin derivatives. The latter could then undergo acid-mediated carbocation formation followed by nucleophilic treatment to give different products, depending on the nature of the nucleophile reagent. Treatment of (E)- and/or (Z)-2-ethylidene-3-hydroxy-5-cyano-3,7,8,12,13,17,18-heptaethylchlorin nickel complex with a mixture of 5% trifluoroacetic acid and dichloromethane yielded a novel type porphyrin-porphyrin dimer with a condensed cyclohexane ring in an almost quantitative yie
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30

Tanner, David, Hua Ming He, and Peter Somfai. "Regioselective nucleophilic ring opening of 2,3-aziridino alcohols." Tetrahedron 48, no. 29 (1992): 6069–78. http://dx.doi.org/10.1016/s0040-4020(01)89855-0.

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31

Leeper, Finian J., and Padma Padmanabhan. "Stereospecific nucleophilic ring-opening of a deuteriated cyclopropylcarbinol." Tetrahedron Letters 30, no. 37 (1989): 5017–20. http://dx.doi.org/10.1016/s0040-4039(01)80570-0.

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32

Kirshenbaum, Kenneth S., and K. Barry Sharpless. "Regioselective Nucleophilic Opening oferythro-andthreo-2,3-Epoxy Alcohols." Chemistry Letters 16, no. 1 (1987): 11–14. http://dx.doi.org/10.1246/cl.1987.11.

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33

GAUTUN, H. S. H., and P. H. J. CARLSEN. "ChemInform Abstract: Nucleophilic Ring Opening of Cyclic Sulphamidites." ChemInform 27, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199601162.

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34

Tayama, Eiji, та Kohei Kawai. "Synthesis of tertiary alkyl fluorides and chlorides by site-selective nucleophilic ring-opening reaction of α-aryl azetidinium salts". RSC Advances 11, № 62 (2021): 39607–18. http://dx.doi.org/10.1039/d1ra08706a.

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35

Muzammil, Ezzah M., Anzar Khan, and Mihaiela C. Stuparu. "Post-polymerization modification reactions of poly(glycidyl methacrylate)s." RSC Advances 7, no. 88 (2017): 55874–84. http://dx.doi.org/10.1039/c7ra11093f.

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36

Bakhtin, S. G., E. N. Shved, and Yu N. Bespal’ko. "Are amines basic or nucleophilic catalysts for oxirane ring opening by proton-donating nucleophiles?" Kinetics and Catalysis 57, no. 1 (2016): 47–51. http://dx.doi.org/10.1134/s002315841601002x.

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37

Dong, Jun, and Jiaxi Xu. "NBS/DMSO-mediated synthesis of (2,3-dihydrobenzo[b][1,4]oxathiin-3-yl)methanols from aryloxymethylthiiranes." New Journal of Chemistry 42, no. 11 (2018): 9037–44. http://dx.doi.org/10.1039/c8nj01117f.

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(2,3-Dihydrobenzo[b][1,4]oxathiin-3-yl)methanols are synthesized from aryloxymethylthiiranes via NBS-mediated aromatic electrophilic substitution, DMSO nucleophilic ring-opening, and water displacement.
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38

Bousfiha, Asmae, Abdou K. D. Dimé, Amelle Mankou-Makaya, et al. "Regioselective C–H amination of free base porphyrins via electrogenerated pyridinium-porphyrins and stabilization of easily oxidized amino-porphyrins by protonation." Chemical Communications 56, no. 6 (2020): 884–87. http://dx.doi.org/10.1039/c9cc07351e.

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Four free base aminoporphyrins were synthesized in two steps via regioselective anodic nucleophilic substitution with pyridine followed by ring opening of the electrogenerated pyridinium with piperidine.
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39

Mostafa, Mai A., Magdy A. Ibrahim, S. S. Ibrahim, Nada Mohamed, and Al-Shimaa Badran. "Synthetic approaches for novel 3-heteroaryl-4-hydroxy-1-methylquinoline-2(1H)one: spectroscopic characterization, molecular docking and DFT investigations." RSC Advances 15, no. 9 (2025): 6718–36. https://doi.org/10.1039/d5ra00325c.

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40

Memarian, Hamaid R., Gholrokh Shokuhimehr та Mousa Soleymani. "Photocatalytic Ring Opening of α-Epoxyketones in Cyclopentanone". Zeitschrift für Naturforschung B 66, № 6 (2011): 603–10. http://dx.doi.org/10.1515/znb-2011-0608.

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Electron transfer-induced ring opening of α-epoxyketones by 2,4,6-triphenylpyrylium tetrafluoroborate (TPT) in cyclopentanone resulted in the diastereoselective formation of 2,5-dioxaspiro[4,4]- nonanes through Cα-O bond cleavage and following nucleophilic attack of cyclopentanone to radical cation intermediates. The readiness for ring opening is influenced by the nature and the location of the additional s`ubstituent on the α-epoxyketones.
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41

Xu, Chuangchuang, Wenlai Xie, and Jiaxi Xu. "Metal-free and regiospecific synthesis of 3-arylindoles." Organic & Biomolecular Chemistry 18, no. 14 (2020): 2661–71. http://dx.doi.org/10.1039/d0ob00317d.

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A microwave-assisted acid and base co-catalyzed strategy shows high efficiency in the synthesis of 3-arylindoles through tandem nucleophilic ring-opening and Fischer indolization of aryloxiranecarbonitriles and arylhydrazine hydrochlorides.
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42

Wang, Zhaobin, Zhilong Chen, and Jianwei Sun. "Catalytic asymmetric nucleophilic openings of 3-substituted oxetanes." Org. Biomol. Chem. 12, no. 32 (2014): 6028–32. http://dx.doi.org/10.1039/c4ob00920g.

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43

Shang, Jiaojiao, Shaojian Lin, and Patrick Theato. "Fabrication of color changeable CO2 sensitive nanofibers." Polymer Chemistry 8, no. 48 (2017): 7446–51. http://dx.doi.org/10.1039/c7py01628j.

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A CO<sub>2</sub> sensor was fabricated by attaching CO<sub>2</sub>-sensitive spiropyran groups onto versatile photo-crosslinked poly(glycidyl methacrylate) (PGMA) precursor nanofibers via a nucleophilic ring-opening reaction.
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44

Amantini, David, Francesco Fringuelli, Oriana Piermatti, Simone Tortoioli, and Luigi Vaccaro. "Nucleophilic ring opening of 1,2-epoxides in aqueous medium." Arkivoc 2002, no. 11 (2003): 293–311. http://dx.doi.org/10.3998/ark.5550190.0003.b26.

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45

Baravkar, Sachin B., Arup Roy, Rupesh L. Gawade, Vedavati G. Puranik, and Gangadhar J. Sanjayan. "Nucleophilic Ring-Opening of Benzoxazinones by DBU: Some Observations." Synthetic Communications 44, no. 20 (2014): 2955–60. http://dx.doi.org/10.1080/00397911.2014.910529.

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46

Alexakis, Alexandre, Emmanuel Vrancken, and Pierre Mangeney. "Enantioselective Nucleophilic Opening of meso Epoxides by Organolithium Reagents." Synlett 1998, no. 10 (1998): 1165–67. http://dx.doi.org/10.1055/s-1998-5741.

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47

Soldaini, Gianluca, Francesca Cardona, and Andrea Goti. "Methyltrioxorhenium catalyzed domino epoxidation-nucleophilic ring opening of glycals." Tetrahedron Letters 44, no. 30 (2003): 5589–92. http://dx.doi.org/10.1016/s0040-4039(03)01386-8.

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48

Avilov, Dmitry V., Mahesh G. Malusare, Engin Arslancan, and Donald C. Dittmer. "A Telluride-Triggered Nucleophilic Ring Opening of Monoactivated Cyclopropanes1." Organic Letters 6, no. 13 (2004): 2225–28. http://dx.doi.org/10.1021/ol0492804.

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49

Duhamel, Pierre, Bertrand Leblond та Jean-Marie Poirier. "Nucleophilic fluorination by selective ring opening of α-halooxiranes". J. Chem. Soc., Chem. Commun., № 5 (1993): 476–77. http://dx.doi.org/10.1039/c39930000476.

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50

Concellon, Jose M., Pablo L. Bernad, and Juan A. Perez-Andres. "ChemInform Abstract: Nucleophilic Ring Closure and Opening of Aminoiodohydrins." ChemInform 31, no. 21 (2010): no. http://dx.doi.org/10.1002/chin.200021054.

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