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Journal articles on the topic 'Nucleophile Substitutionen'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Pritzkow, Wilhelm. "Nucleophile Substitutionen nach dem Eliminierungs-Additions-Mechanismus." Zeitschrift für Chemie 10, no. 9 (2010): 330–38. http://dx.doi.org/10.1002/zfch.19700100903.

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2

Lippmann, Eberhard, Andreas Könnecke, and Gerhard Beyer. "Nucleophile Substitutionen am 2-Phenyl-5-chlormethyl-tetrazol." Zeitschrift für Chemie 15, no. 3 (2010): 102–3. http://dx.doi.org/10.1002/zfch.19750150307.

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3

Vilotijevic, Ivan, Markus Lange, and You Zi. "Latent (Pro)Nucleophiles in Enantioselective Lewis Base Catalyzed Allylic Substitutions." Synlett 31, no. 13 (2020): 1237–43. http://dx.doi.org/10.1055/s-0040-1707130.

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The use of latent nucleophiles, which are molecules that are not nucleophilic but can be activated to act as a nucleophile at an opportune time during the reaction, expands the scope of Lewis base catalyzed reactions. Here, we provide an overview of the concept and show examples of applications to N- and C-centered nucleophiles in allylic substitutions. N- and C-silyl compounds are superior latent (pro)nucleophiles in Lewis base catalyzed reactions with allylic fluorides in which the formation of the strong Si–F bond serves as the driving force for the reactions. The latent (pro)nucleophiles e

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4

Rueping, Magnus, Boris J Nachtsheim, Stefan A Moreth, and Michael Bolte. "Asymmetrische Brønsted-Säure-Katalyse: enantioselektive nucleophile Substitutionen und 1,4-Additionen." Angewandte Chemie 120, no. 3 (2008): 603–6. http://dx.doi.org/10.1002/ange.200703668.

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5

Cotarca, Livius, R. Bacaloglu, C. Csunderlik, N. Marcu, and A. Tarnaveanu. "Nucleophile Substitutionen an Kohlensäurederivaten. XX. Aminolyse des Bis(trichlormethyl)carbonates." Journal für Praktische Chemie 329, no. 6 (1987): 1052–62. http://dx.doi.org/10.1002/prac.19873290616.

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6

Schubert, Hermann, Helmut Simon, and Alfred Jumar. "Weitere nucleophile Substitutionen an alkylierten 4-Nitro-5-chlor-imidazolen." Zeitschrift für Chemie 8, no. 2 (2010): 62–63. http://dx.doi.org/10.1002/zfch.19680080208.

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7

Beger, J., R. Neumann, K. Gloe, and P. Mühl. "Nucleophile Substitutionen an Bischlornitrosoverbindungen. IV. Sulfonylaminooxime als Extraktionsmittel für Kupfer(II)." Journal für Praktische Chemie 330, no. 5 (1988): 683–94. http://dx.doi.org/10.1002/prac.19883300503.

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8

Beger, J., and R. Neumann. "Nucleophile Substitutionen an Bischlornitrosoverbindungen. V. Mehrfunktionelle neutrale Komplex-Liganden mit Oximendgruppen." Journal f�r Praktische Chemie 331, no. 2 (1989): 354–60. http://dx.doi.org/10.1002/prac.19893310223.

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9

Cotarca, Livius, Radu Bacaloglu, Nicolae Marcu, and Alexandru Târnaveanu. "Nucleophile Substitutionen an Kohlensäurederivaten. XIX. Alkoholyse und Hydrolyse des Bis(trichlormethyl)carbonates." Journal für Praktische Chemie 327, no. 6 (1985): 881–86. http://dx.doi.org/10.1002/prac.19853270602.

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10

Tsuji, Yutaka, and John P. Richard. "Swain–Scott relationships for nucleophile addition to ring-substituted phenonium ions." Canadian Journal of Chemistry 93, no. 4 (2015): 428–34. http://dx.doi.org/10.1139/cjc-2014-0337.

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The products of the reactions of 2-(4-methoxyphenyl)ethyl tosylate (MeO-1-OTs) and 2-(4-methyphenyl)ethyl tosylate (Me-1-OTs) with nucleophilic anions were determined for reactions in 50:50 (v/v) trifluoroethanol (TFE) / water at 25 °C. In many cases, the nucleophile selectivity kNu/ks ((mol/L)−1) for reactions of nucleophile and solvent, calculated from the ratio of product yields, depends upon [Nu−]. This demonstrates the existence of competing reaction pathways, which show different selectivities for reactions with nucleophiles. A 13C NMR analysis of the products of the reactions of substra

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11

Kolodiazhnyi, Oleg I. "Stereochemistry of electrophilic and nucleophilic substitutions at phosphorus." Pure and Applied Chemistry 91, no. 1 (2019): 43–57. http://dx.doi.org/10.1515/pac-2018-0807.

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Abstract Nucleophilic and electrophilic substitutions are the most often applied reactions in organophosphorus chemistry. They are closely interrelated, because in a reacting pair always one reagent is an electrophile, and another nucleophile. The reactions of electrophilic and nucleophilic substitutions at the phosphorus center proceed via the formation of a pentacoordinated intermediate. The mechanism of nucleophilic substitution involves the exchange of ligands in the pentacoordinate phosphorane intermediate, leading to the more stable stereomer under the thermodynamic control. Electrophili

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12

Selimović, Enisa, and Tanja Soldatović. "Study on the reactions between dichlorido[2,2′:6′,2″-terpyridine] zinc(II) and biologically relevant nucleophiles in aqueous solution." Progress in Reaction Kinetics and Mechanism 44, no. 2 (2019): 105–13. http://dx.doi.org/10.1177/1468678319825724.

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Substitution reactions of square-pyramidal [ZnCl2(terpy)] complex (terpy = 2,2′:6′,2″-terpyridine) with biologically relevant nucleophiles such as imidazole, glutathione, 1,2,4-triazole, and pyrazine were investigated at pH 7.0 as a function of nucleophile concentration. The reactions were followed under pseudo first-order conditions by UV-Vis spectrophotometry. The substitution reactions comprised two steps of consecutive displacement of chlorido ligands. Different reaction pathways for the first reaction step of nucleophilic substitution were defined. The order of reactivity of the investiga

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13

Giraudeau, Alain, та Lana El Kahef. "β-Substitution de la méso-tétraphénylporphyrine de zinc par voie électrochimique". Canadian Journal of Chemistry 69, № 7 (1991): 1161–65. http://dx.doi.org/10.1139/v91-173.

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The electrochemical oxidation of the zinc tetraphenylporphyrin complex in a mixed acetonitrile–dichloroethane solution in the presence of nucleophiles (Py, 3-Pic, [Formula: see text], SCN−) leads to the formation of the corresponding monosubstituted metalloporphyrin. For each of these nucleophiles the substitution occurs at a pyrrole carbon atom (β-substitution). The electrochemical conditions of these substitutions are discussed and an overall reaction is proposed. Key words: porphyrins, electrochemical reactions, nucleophilic substitution.

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14

Purwono, Bambang, and Estiana E. P. Daruningsih. "NUCHLEOPHILIC SUBSTITUTION REACTION OF CYANIDE AND METHOXYDE IONS TO QUATERNARY MANNICH BASE FROM VANILLIN." Indonesian Journal of Chemistry 7, no. 1 (2010): 58–60. http://dx.doi.org/10.22146/ijc.21713.

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The nucleophilic substitution reaction to quaternary Mannich base from vanillin has been investigated. Mannich reaction to vanillin was carried out by refluxing mixture of vanillin, formaldehyde and dimethyl amine. Quaternary ammonium halide salt was obtained from reaction of Mannich vanillin base with methyl iodide in THF solvents and yielded 93.28%. Nucleophilic substituion to the halide salts with cyanide nucleophile produced 4-hidroxy-3-methoxy-5-(cyano)methylbenzaldehyde in 54.39% yield, with methoxyde ion obtained 4-hidroxy- 3-methoxy-5-(methoxy)-methyl-benzaldehide in 67.80% yield. The

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15

Sheyi, Rotimi, Anamika Sharma, Ayman El-Faham, Beatriz G. de la Torre, and Fernando Albericio. "Phenol as a Modulator in the Chemical Reactivity of 2,4,6-Trichloro-1,3,5-triazine: Rules of the Game II." Australian Journal of Chemistry 73, no. 4 (2020): 352. http://dx.doi.org/10.1071/ch19524.

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2,4,6-Trichloro-1,3,5-triazine (TCT) is a privileged core that has the capacity to undergo sequential nucleophilic substitution reactions. Three nucleophiles, namely phenol, thiol and amine, were studied and the preferential order of incorporation on TCT was found to be first phenol, second thiol and third amine. The introduction of phenol was achieved at −20°C. The incorporation of this nucleophile in TCT helped to replace the third ‘Cl’ at 35°C, which is compatible with a biological context. The atomic charges on ‘Cl’ calculated by theoretical approaches were consistent with the experimental

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16

Zhang, Xiao, Guo-ping Lu, and Chun Cai. "Facile aromatic nucleophilic substitution (SNAr) reactions in ionic liquids: an electrophile–nucleophile dual activation by [Omim]Br for the reaction." Green Chemistry 18, no. 20 (2016): 5580–85. http://dx.doi.org/10.1039/c6gc01742h.

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17

Purwono, Bambang, and Estiana R. P. Daruningsih. "NUCLEOPHILIC SUBSTITUTION REACTION OF CYANIDE AND METHOXYDE IONS TO QUATERNARY MANNICH BASE FROM VANILLIN." Indonesian Journal of Chemistry 5, no. 3 (2010): 203–6. http://dx.doi.org/10.22146/ijc.21789.

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The nucleophilic substitution reaction to quaternary Mannich base from vanillin has been investigated. Mannich reaction to vanillin was carried out by refluxing mixture of vanillin, formaldehyde and dimethyl amine. Quaternary ammonium halide salt was obtained from reaction of Mannich vanillin base with methyl iodide in THF solvents and yielded 93.28 %. Nucleophilic substituion to the halide salts with cyanide nucleophile produced 4-hidroxy-3-methoxy-5-(cyano)methylbenzaldehyde in 54.39% yield. Reaction with methoxyde ion yielded 4-hydroxy- 3-methoxy-5-(methoxy) -methylbenzaldehyde in 67.80% yi

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18

Crossley, Maxwell J., Lionel G. King, Simon M. Pyke, and Charles W. Tansey. "Reaction of 5-nitro-octaethylporphyrins with nucleophiles." Journal of Porphyrins and Phthalocyanines 06, no. 11 (2002): 685–94. http://dx.doi.org/10.1142/s1088424602000816.

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An investigation of the reactions of metallo-5-nitro-2,3,7,8,12,13,17,18-octaethylporphyrins with Grignard reagents, benzyl oxide, phenoxide and benzenethiolate nucleophiles shows that, except for benzenethiolate reactions, they are less efficient than related reactions of metallo-2-nitro-5,10,15,20-tetraarylporphyrins. Treatment of free-base and nickel(II) 5-nitro-octaethylporphyrin with the “soft” nucleophile benzenethiolate in DMF affords the corresponding 5-phenylthioporphyrins in 61 and 72% yield, respectively, by ipso-substitution of the nitro group. In contrast, with methylmagnesium iod

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19

Bakardjiev, Mário, Suzan El Anwar, Dmytro Bavol, Zdeňka Růžičková, and Bohumír Grűner. "Focus on Chemistry of the 10-Dioxane-nido-7,8-dicarba-undecahydrido Undecaborate Zwitterion; Exceptionally Easy Abstraction of Hydrogen Bridge and Double-Action Pathways Observed in Ring Cleavage Reactions with OH− as Nucleophile." Molecules 25, no. 4 (2020): 814. http://dx.doi.org/10.3390/molecules25040814.

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Ring cleavage of cyclic ether substituents attached to a boron cage via an oxonium oxygen atom are amongst the most versatile methods for conjoining boron closo-cages with organic functional groups. Here we focus on much less tackled chemistry of the 11-vertex zwitterionic compound [10-(O-(CH2-CH2)2O)-nido-7,8-C2B9H11] (1), which is the only known representative of cyclic ether substitution at nido-cages, and explore the scope for the use of this zwitterion 1 in reactions with various types of nucleophiles including bifunctional ones. Most of the nitrogen, oxygen, halogen, and sulphur nucleoph

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20

Liljenberg, Magnus, Tore Brinck, Tobias Rein та Mats Svensson. "Utilizing the σ-complex stability for quantifying reactivity in nucleophilic substitution of aromatic fluorides". Beilstein Journal of Organic Chemistry 9 (23 квітня 2013): 791–99. http://dx.doi.org/10.3762/bjoc.9.90.

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A computational approach using density functional theory to compute the energies of the possible σ-complex reaction intermediates, the “σ-complex approach”, has been shown to be very useful in predicting regioselectivity, in electrophilic as well as nucleophilic aromatic substitution. In this article we give a short overview of the background for these investigations and the general requirements for predictive reactivity models for the pharmaceutical industry. We also present new results regarding the reaction rates and regioselectivities in nucleophilic substitution of fluorinated aromatics.

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21

McNeish, Joanne R., J. Scott Parent, and Ralph A. Whitney. "Halogenated poly(isobutylene-co-isoprene): influence of halogen leaving-group and polymer microstructure on chemical reactivity." Canadian Journal of Chemistry 91, no. 6 (2013): 420–27. http://dx.doi.org/10.1139/cjc-2013-0068.

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Brominated (BIIR) and chlorinated (CIIR) poly(isobutylene-co-isoprene) are commercially available materials commonly known as halobutyl rubbers. The effect of leaving-group ability on the reactivity of halogenated poly(isobutylene-co-isoprene) was studied to place iodobutyl rubber reactivity into context with these materials. The effect of microstructure on reactivity of existing commercial materials was studied through comparison to that of polymers containing rearranged halomethyl (r-CIIR, r-BIIR, and r-IIIR) microstructure (prepared from as-received BIIR). The effect of leaving group on bot

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22

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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23

Dust, Julian M., and Richard A. Manderville. "Carbon versus oxygen nucleophilic selectivity in the reaction of the aryloxide ions, 2,6- and 3,5-di-tert-butylphenoxide, with the 2-[(nitro)\dn6 xaryl]-4,6-dinitrobenzotriazole 1-oxide series of super-electrophiles. Stereoelectronic factors on C-7 Meisenheimer complex formation versus C-1' SNAr displacement." Canadian Journal of Chemistry 76, no. 6 (1998): 662–71. http://dx.doi.org/10.1139/v98-028.

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The 2-[(nitro)xaryl]-4,6-dinitrobenzotriazole 1-oxides (1, Pi-DNBT (x = 3); 2, DNP-DNBT (x = 2); 3, NP-DNBT (x = 1)) are electron-deficient nitro-substituted heteroaromatic substrates that possess two sites for nucleophilic attachment: C-7 and C-1'. Generally, attack at the super-electrophilic C-7 site yields spectroscopically observable anionic sigma -bonded adducts, whereas attack at C-1' leads to displacement products in an overall process of nucleophilic aromatic substitution (SNAr). To gain an understanding of the factors affecting C-1' versus C-7 attack by potentially ambident aryloxide

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24

Hudson, R., N. P. Bizier, K. N. Esdale, and J. L. Katz. "Synthesis of indoles, benzofurans, and related heterocycles via an acetylene-activated SNAr/intramolecular cyclization cascade sequence in water or DMSO." Organic & Biomolecular Chemistry 13, no. 8 (2015): 2273–84. http://dx.doi.org/10.1039/c4ob02549k.

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The synthesis of 2-substituted indoles and benzofurans was achieved by nucleophilic aromatic substitution, followed by subsequent 5-endo-dig cyclization between the nucleophile and an ortho acetylene.

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25

Dust, Julian M., та Erwin Buncel. "Reactions of the super-electrophile, 2-(2′,4′-dinitrophenyl)-4,6-dinitrobenzotriazole 1-oxide, with methoxide and tert-butoxide: basicity and steric hindrance as factors in σ-complex formation versus nucleophilic displacement". Canadian Journal of Chemistry 69, № 6 (1991): 978–86. http://dx.doi.org/10.1139/v91-143.

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The course of the reactions of methoxide and tert-butoxide with 2-(2′,4′-dinitrophenyl)-4,6-dinitrobenzotriazole 1-oxide (4) clearly shows that the C-7 electrophilic site is significantly more reactive than the C-1′ site of the substrate. The reaction pathways of these alkoxides, which differ in basicity (as a measure of nucleophilicity) and steric bulk, were followed by 400 MHz 1H nuclear magnetic resonance spectroscopy. While both alkoxides lead to immediate formation of the respective C-7 anionic σ-adducts, a greater percentage of C-7 adduct formation occurs with methoxide as attacking nucl

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26

Ajenjo, Javier, Martin Greenhall, Camillo Zarantonello, and Petr Beier. "Synthesis and nucleophilic aromatic substitution of 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzene." Beilstein Journal of Organic Chemistry 12 (February 3, 2016): 192–97. http://dx.doi.org/10.3762/bjoc.12.21.

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3-Fluoro-5-nitro-1-(pentafluorosulfanyl)benzene was prepared by three different ways: as a byproduct of direct fluorination of 1,2-bis(3-nitrophenyl)disulfane, by direct fluorination of 4-nitro-1-(pentafluorosulfanyl)benzene, and by fluorodenitration of 3,5-dinitro-1-(pentafluorosulfanyl)benzene. The title compound was subjected to a nucleophilic aromatic substitution of the fluorine atom with oxygen, sulfur and nitrogen nucleophiles affording novel (pentafluorosulfanyl)benzenes with 3,5-disubstitution pattern. Vicarious nucleophilic substitution of the title compound with carbon, oxygen, and

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27

Fang, Yao-ren, Zhu-gen Lai, and Kenneth Charles Westaway. "Isotope effects in nucleophilic substitution reactions X. The effect of changing the nucleophilic atom on ion-pairing in an SN2 reaction." Canadian Journal of Chemistry 76, no. 6 (1998): 758–64. http://dx.doi.org/10.1139/v98-056.

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The effect of ion-pairing in an SN2 reaction is very different when the nucleophilic atom is changed from sulfur to oxygen, i.e., changing the nucleophile from thiophenoxide ion to phenoxide ion. When the nucleophile is sodium thiophenoxide, ion-pairing markedly alters the secondary α -deuterium kinetic isotope effect (transition state structure) and the substituent effect found by changing the para substituent on the nucleophile. When the nucleophile is sodium phenoxide, ion-pairing does not significantly affect the secondary α -deuterium or the chlorine leaving group kinetic isotope effects

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28

Richter, Wolf Jürgen. "Asymmetrische Synthesen durch Substitution: Diastereomere Arsinite aus homochiral substituierten Arsoniten / Asymmetrie Synthesis via Substitution: Diastereomeric Arsinites from Homochirally Substituted Arsonites." Zeitschrift für Naturforschung B 50, no. 3 (1995): 339–41. http://dx.doi.org/10.1515/znb-1995-0306.

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Conceptually novel access to chiral arsinites is provided by reacting phenyl-O,O-dimenthylarsonite (1) with bulky nucleophiles e. g. tert-butyl-lithium or iso-propyl-lithium to yield the arsinites 3 and 4. The asymmetric induction determined by GC and NMR is 50% and 30% d.e. A small nucleophile effects double substitution.

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29

Cherubim, P., and LW Deady. "Nucleophilic Substitution Reactions in Benzo[C][1,8]naphthyridines. II." Australian Journal of Chemistry 43, no. 8 (1990): 1469. http://dx.doi.org/10.1071/ch9901469.

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3-Chloro-1-methyl-6-(p- methylphenoxy ) benzo [c][1,8] naphthyridine has been prepared, the reactions with various nitrogen, oxygen and sulfur nucleophiles studied, and the results compared with those for the 1- chloro-3-methyl isomer. The 6-position was more reactive for oxygen and nitrogen nucleophiles, so much so that an initially added 6-NHR group was displaced by a second R′NH2 nucleophile at least as readily as was the 3-chloro group. With p- chloro ( thiophenol ), however, the 3-chloro group was preferentially displaced.

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30

Arcadi, Antonio, Giancarlo Fabrizi, Andrea Fochetti, et al. "Palladium-catalyzed Tsuji–Trost-type reaction of benzofuran-2-ylmethyl acetates with nucleophiles." RSC Advances 11, no. 2 (2021): 909–17. http://dx.doi.org/10.1039/d0ra09601f.

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31

Negrimovsky, Vladimir, Konstantin Volkov, Kyrill Suponitsky, and Evgeny Lukyanets. "C-Nucleophilic substitution in tetrachlorophthalonitrile — An approach to some new hexadecasubstituted phthalocyanines." Journal of Porphyrins and Phthalocyanines 17, no. 08n09 (2013): 799–806. http://dx.doi.org/10.1142/s1088424613500429.

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Reaction of tetrachlorophthalonitrile with some C -nucleophiles was studied. Only one chlorine atom was substituted regioselectively in the position 4 of benzene ring with diethyl malonate and malononitrile; no reaction occurred in case of bulkier diethyl ethylmalonate and ethylmalononitrile. In case of dimedone the domino substitution of two chlorine atoms, first with C -nucleophile followed by enolate O -nucleophile led to the mixture of two dibenzofuran derivatives. Remaining chlorine aroms n malonate and dibenzofuran derivatives were substituted with thiols, but in malononitrile derivative

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32

Lu, Ju-You, Bo Zhao, Yongmei Du, Jianxin Yang, and Jian Lu. "Transition-metal-free direct nucleophilic substitution of carboranyllithium and 2-halopyridines." Organic & Biomolecular Chemistry 17, no. 32 (2019): 7438–41. http://dx.doi.org/10.1039/c9ob00978g.

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An efficient C(cage)–heteroarylation of carborane is presented, via direct nucleophilic substitution of carboranyllithium with 2-halopyridines under transition-metal-free conditions. The process utilizes readily available carboranyllithium nucleophile, and exhibits a broad substrate scope.

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33

Zhang, Xiao, Guo-ping Lu, and Chun Cai. "Correction: Facile aromatic nucleophilic substitution (SNAr) reactions in ionic liquids: an electrophile–nucleophile dual activation by [Omim]Br for the reaction." Green Chemistry 18, no. 22 (2016): 6143. http://dx.doi.org/10.1039/c6gc90108e.

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Correction for ‘Facile aromatic nucleophilic substitution (S<sub>N</sub>Ar) reactions in ionic liquids: an electrophile–nucleophile dual activation by [Omim]Br for the reaction’ by Xiao Zhang, et al., Green Chem., 2016, 18, 5580–5585.

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34

Keddie, Neil S., Pier Alexandre Champagne, Justine Desroches, Jean-François Paquin, and David O'Hagan. "Stereochemical outcomes of C–F activation reactions of benzyl fluoride." Beilstein Journal of Organic Chemistry 14 (January 9, 2018): 106–13. http://dx.doi.org/10.3762/bjoc.14.6.

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In recent years, the highly polar C–F bond has been utilised in activation chemistry despite its low reactivity to traditional nucleophiles, when compared to other C–X halogen bonds. Paquin’s group has reported extensive studies on the C–F activation of benzylic fluorides for nucleophilic substitutions and Friedel–Crafts reactions, using a range of hydrogen bond donors such as water, triols or hexafluoroisopropanol (HFIP) as the activators. This study examines the stereointegrity of the C–F activation reaction through the use of an enantiopure isotopomer of benzyl fluoride to identify whether

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35

Nudelman, Norma Sbarbati, Cecilia E. Silvana Alvaro, Monica Savini, Viviana Nicotra, and Jeannette Yankelevich. "Effects of the Nucleophile Structure on the Mechanisms of Reaction of 1-Chloro-2,4-dinitrobenzene with Aromatic Amines in Aprotic Solvents." Collection of Czechoslovak Chemical Communications 64, no. 10 (1999): 1583–93. http://dx.doi.org/10.1135/cccc19991583.

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The kinetics of reactions of 1-chloro-2,4-dinitrobenzene with aniline and several substituted aromatic amines, B, in toluene shows a quadratic dependence of the second-order rate constant, kA, on [B], which is preserved even in the presence of increasing amounts of dimethylaniline, while the reaction with N-methylaniline shows a linear dependence of kA vs [B]. All these results are interpreted by the "dimer nucleophile" mechanism, and confirmed by the effects of a non-nucleophilic hydrogen bond acceptor tertiary amine which show the relevance of the structure of the nucleophile and the role of

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36

Li, Jinhua, Zhengyu Lu, Yuhui Hua, Dafa Chen, and Haiping Xia. "Carbolong chemistry: nucleophilic aromatic substitution of a triflate functionalized iridapentalene." Chemical Communications 57, no. 68 (2021): 8464–67. http://dx.doi.org/10.1039/d1cc03261e.

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37

Kočovský, Pavel, and Andrei V. Malkov. "Asymmetric synthesis: From transition metals to organocatalysis." Pure and Applied Chemistry 80, no. 5 (2008): 953–66. http://dx.doi.org/10.1351/pac200880050953.

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Umpolung in the allylation reaction is discussed with examples drawn from transition-metal-catalyzed allylic substitution (with the allylic unit acting as an electrophile) and Lewis base-catalyzed allylation of aldehydes with allyltrichlorosilane (with the allyl acting as a nucleophile). Iridium-catalyzed electrophilic allylation of O-nucleophiles has been employed in our new approach to C-nucleoside analogs, where the C-O bond (rather than C-C) was constructed stereospecifically. Variation of the absolute configuration in the starting segments allowed the synthesis of all four combinations of

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38

Vasilenko, Dmitry A., Sevastian E. Dronov, Dzianis U. Parfiryeu, et al. "5-Nitroisoxazoles in SNAr reactions: access to polysubstituted isoxazole derivatives." Organic & Biomolecular Chemistry 19, no. 29 (2021): 6447–54. http://dx.doi.org/10.1039/d1ob00816a.

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An efficient protocol for the straightforward functionalization of the isoxazole ring via the reactions of aromatic nucleophilic substitution of the nitro group with various nucleophiles has been elaborated.

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39

Bruneau, Christian, Jean-Luc Renaud, and Bernard Demerseman. "Ruthenium catalysts for selective nucleophilic allylic substitution." Pure and Applied Chemistry 80, no. 5 (2008): 861–71. http://dx.doi.org/10.1351/pac200880050861.

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Recent developments in the chemistry of η3-allylruthenium(IV) complexes are due to their straightforward synthesis resulting from oxidative addition of allylic substrates to a ruthenium(II) center. Subsequent reaction with a nucleophile is the basis of their involvement in the catalytic allylic substitution reaction. We focus here on ruthenium-catalyzed substitution of allylic substrates by C-, N-, and O-nucleophiles and show that selected ligands make regio- and enantioselective reactions possible.

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40

Weiss, Robert, Matthias Handke, Silvia Reichel, and Frank Hampel. "Onio-assistierte SN2-Reaktionen: Allgemeiner Zugang zu symmetrischen und unsymmetrischen geminal bisoniosubstituierten Methanderivaten / Onio-Assisted SN2-Reactions: General Access to Symmetrical and Unsymmetrical Geminally Bisonio Substituted Methane Derivatives." Zeitschrift für Naturforschung B 53, no. 5-6 (1998): 599–619. http://dx.doi.org/10.1515/znb-1998-5-618.

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Abstract The arsonium salt [Ph3As-CH2-OTf]+ OTf- 11a contains a 1,1-biselectrophilic Csp3 center which permits to synthesize a wide range of symmetrical and unsymmetrical geminally bisonio-substituted methane derivatives. With neutral nucleophiles INu under mild condi- tions a series of 1.1-bisonium salts [Ph3As-CH2-Nu]2+ 2OTf- 12-23 is obtained in good yields. Under more stringent conditions the triphenylarsonio function in these salts can also be mobilized as a nucleofuge in a subsequent SN-reaction with a second nucleophile | Nu’, yielding a series of novel unsymmetrical 1,1-bisonium salts

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Deady, LW, and DM Werden. "Nucleophilic-Substitution Reactions in Benzo[C][1,8]Naphthyridines." Australian Journal of Chemistry 39, no. 4 (1986): 667. http://dx.doi.org/10.1071/ch9860667.

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The reactions of 1-chloro-3-methyl-6-(p- methylphenoxy ) benzo [c][1,8] naphthyridine with a variety of nucleophiles are reported. The relative reactivity of the 1- and 6-positions depends on the nucleophile and reaction conditions. Anilines, and alkyl and aryl thioxides react at position 1, alkylamines and alkoxide at position 6, and acidified alcohol at both 1 and 6. Some possible reasons for these positional reactivities are discussed.

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Vrancken, Emmanuel, Marwa Ayadi, Pierre Mpawenayo, Farhat Rezgui, Eric Leclerc, and Jean-Marc Campagne. "Catalytic Direct Nucleophilic Substitution of Primary Morita–Baylis–Hillman Adducts and Application to the Straightforward Synthesis of Dihydroisoindolones." Synthesis 50, no. 05 (2017): 1166–74. http://dx.doi.org/10.1055/s-0036-1589131.

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An interesting γ-carbonyl effect permits the dual iron/boron-catalyzed direct nucleophilic substitution of functionalized primary allylic alcohols with a large variety of nucleophiles. The resulting substitution products are useful synthetic platforms for heterocycle synthesis, as illustrated in a ready access to tetrahydroisoindol-4-ones.

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Dolliver, Debra D., David B. Delatte, Derek B. Linder, James E. Johnson, Diana C. Canesco, and Jeffrey E. Rowe. "Nucleophilic substitution reactions of N-alkoxyimidoyl fluorides by carbon nucleophiles." Canadian Journal of Chemistry 85, no. 11 (2007): 913–22. http://dx.doi.org/10.1139/v07-097.

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Nucleophilic substitutions of N-alkoxybenzoimidoyl fluorides [p-ClArC(F)=NOR; R = CH3, i-Pr] by enolate-type ions have been performed to produce compounds that can exist in two tautomeric forms: the imine form{p-ClArC(Y)=NOR [Y = CH(CN)2, CH(CN)(CO2Et), CH(CO2Et)2]}or the enamine form {p-ClArC(NHOR)=C(R1)(R2) [R1, R2 = CN, CO2Et]}. These compounds display varying ratios of imine–enamine tautomerizm in chloroform: the diester compound exists almost solely in the imine form, the dicyano compound exists solely in the enamine form, and the cyano-ester compound exists in both tautomeric forms. Comp

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Kutschy, Peter, Pavol Kristian, Milan Dzurilla, Dušan Koščík, and Róbert Nádaskay. "Selectivity of nucleophilic addition to and substitution at isothiocyanatocarbonyl group. Reactions of 4-pentinoyl- and 2-(2-propinyl)-4-pentinoyl isothiocyanate with amines and methanol." Collection of Czechoslovak Chemical Communications 52, no. 4 (1987): 995–1005. http://dx.doi.org/10.1135/cccc19870995.

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4-Pentinoyl isothiocyanate reacts with primary and secondary amines by either nucleophilic addition to N=C=S group to yield the corresponding thioureas, or a nucleophilic substitution at the carbonyl group to give 4-pentinoic acid amides. The less nucleophilic diphenylamine reacts selectively to afford the product of nucleophilic addition only. 2-(2-Propinyl)-4-pentinoyl isothiocyanate, having a sterically hindered carbonyl group, furnished with primary amines a mixture of amides and thioureas, whereas the bulkier secondary amines react selectively to form thioureas only. Both isothiocyanates

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Zhang, Xin, Jingyun Ren, Siu Min Tan, Davin Tan, Richmond Lee, and Choon-Hong Tan. "An enantioconvergent halogenophilic nucleophilic substitution (SN2X) reaction." Science 363, no. 6425 (2019): 400–404. http://dx.doi.org/10.1126/science.aau7797.

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Bimolecular nucleophilic substitution (SN2) plays a central role in organic chemistry. In the conventionally accepted mechanism, the nucleophile displaces a carbon-bound leaving group X, often a halogen, by attacking the carbon face opposite the C–X bond. A less common variant, the halogenophilic SN2X reaction, involves initial nucleophilic attack of the X group from the front and as such is less sensitive to backside steric hindrance. Herein, we report an enantioconvergent substitution reaction of activated tertiary bromides by thiocarboxylates or azides that, on the basis of experimental and

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Schmidt, Andreas, and Thorsten Mordhorst. "Synthesis of Pyridine-Thioethers via Mono- and Tricationic Pyridinium Salts." Zeitschrift für Naturforschung B 60, no. 6 (2005): 683–87. http://dx.doi.org/10.1515/znb-2005-0613.

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On nucleophilic substitution with S-nucleophiles at room temperature, 1-(4-dimethylamino)- [2,3,5,6-tetrachloropyridin-4-yl]pyridinium chloride (2) yielded tetrachloro-4-sulfanylpyridines and 2,3,5-trichloro-4,6-disulfanylpyridines depending on the reaction conditions. Similarly, the tricationic (3,5-dichloropyridine-2,4,6-triyl)-1,1’,1”-tris[4-(dimethylamino)pyridinium] trichloride 3 was reacted with S-nucleophiles to give the corresponding 3,5-trichloro-2,4,6-trisulfanylpyridines under mild conditions.

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Kimura, Tsutomu. "Recent Advances in Magnesium Carbenoid Chemistry." Synthesis 49, no. 23 (2017): 5105–19. http://dx.doi.org/10.1055/s-0036-1590894.

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Magnesium carbenoids are a class of organomagnesium species possessing a halo group at the α-position. The reactions of magnesium carbenoids can be classified into the following three categories: nucleophilic reactions resembling Grignard reagents, electrophilic reactions resembling organic halides, and rearrangements resembling carbenes. This short review summarizes recent studies on magnesium carbenoids reported between 2010 and 2016, and milestone studies reported before 2010 according to the classification of the reactions into the aforementioned three categories.1 Introduction2 Structures

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Ormazábal-Toledo, Rodrigo, Renato Contreras, Ricardo A. Tapia, and Paola R. Campodónico. "Specific nucleophile–electrophile interactions in nucleophilic aromatic substitutions." Organic & Biomolecular Chemistry 11, no. 14 (2013): 2302. http://dx.doi.org/10.1039/c3ob27450k.

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Christoffers, Jens, and Mathias S. Wickleder. "Synthesis of Aromatic and Aliphatic Di-, Tri-, and Tetrasulfonic Acids." Synlett 31, no. 10 (2020): 945–52. http://dx.doi.org/10.1055/s-0039-1691745.

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Oligosulfonic acids are promising linker compounds for coordination polymers and metal-organic frameworks, however, compared to their carboxylic acid congeners, often not readily accessible by established synthetic routes. This Account highlights the synthesis of recently developed aromatic and aliphatic di-, tri- and tetrasulfonic acids. While multiple electrophilic sulfonations of aromatic substrates are rather limited, the nucleophilic aromatic substitution including an intramolecular variant, the Newman–Kwart rearrangement, allows the flexible introduction of up to four sulfur-containing m

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Schmidt, Andreas, and Thorsten Mordhorst. "Syntheses and Properties of Di- and Tricationic Hetarenium-Substituted Pyrimidines." Zeitschrift für Naturforschung B 61, no. 4 (2006): 396–405. http://dx.doi.org/10.1515/znb-2006-0405.

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2,4-Dichloro-, 4,6-dichloro-, 2,4,6-trichloro- and tetrachloropyrimidine undergo nucleophilic displacements by 4-(dimethylamino)pyridine to give (pyrimidine-2,4-diyl)-1,1’-bis[4-(dimethylamino) pyridinium] dichloride, (pyrimidine-4,6-diyl)-1,1’-bis[4-(dimethylamino)-pyridinium] dichloride, (pyrimidine-2,4,6-triyl)-1,1’,1”-tris[4-(dimethylamino)pyridinium] trichloride, and (5- chloropyrimidine-2,4,6-triyl)-1,1’,1”-tris[4-(dimethylamino)pyridinium] trichloride, respectively. Nucleophilic substitutions of the pyridinium substituents by O- and S-nucleophiles to functionalized pyrimidines are exami

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