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Journal articles on the topic 'Substitution reactions. Nucleophilic reactions. Benzene'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Mclure, FI, RK Norris, and K. Wilson. "Nucleophilic Substitution Reactions of Thienyl Neopentyl Substrates." Australian Journal of Chemistry 40, no. 1 (1987): 49. http://dx.doi.org/10.1071/ch9870049.

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The reaction of the chlorides (4)-(6), which are both neopentylic and thenylic , were studied. The chloride (4), unlike its analogue (13) in the benzene series, undergoes ready solvolysis with alcohols to give the corresponding ethers, e.g. (7)-(9). The chlorides (5) and (6) react more slowly than (4) but undergo methanolysis to give the methyl ethers (11) and (12) respectively. In the dipolar aprotic solvents, dimethyl sulfoxide and dimethylformamide, the reactions of the chlorides (4), (5) and (6) with the thiolate salt (16) appear to proceed by an SN1-like, an SN(AEAE) and an SRNl process r

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2

Emokpae, Thomas A., Patrick U. Uwakwe, and Jack Hirst. "The mechanisms of nucleophilic substitution reactions of aromatic ethers with amines in benzene." Journal of the Chemical Society, Perkin Transactions 2, no. 4 (1991): 509. http://dx.doi.org/10.1039/p29910000509.

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3

EMOKPAE, T. A., P. U. UWAKWE, and J. HIRST. "ChemInform Abstract: The Mechanisms of Nucleophilic Substitution Reactions of Aromatic Ethers with Amines in Benzene." ChemInform 22, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.199128055.

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4

Jain, Ajay K., Vinod K. Gupta, and Anurag Kumar. "Aromatic nucleophilic substitution reactions of oxime ethers with aliphatic primary and secondary amines in benzene." Journal of the Chemical Society, Perkin Transactions 2, no. 1 (1990): 11. http://dx.doi.org/10.1039/p29900000011.

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5

Leznoff, Clifford C., and David M. Drew. "The use of bisphthalonitriles in the synthesis of side-strapped 1,11,15,25-tetrasubstituted phthalocyanines." Canadian Journal of Chemistry 74, no. 3 (1996): 307–18. http://dx.doi.org/10.1139/v96-035.

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Nucleophilic aromatic substitution reactions of 3-nitrophthalonitrile yield 3-hydroxyphthalonitrile and 3-neopentoxyphthalonitrile, the latter of which condensed to 1,8,15,22-tetraneopentoxyphthalocyanine as a mixture of isomers. Bisphthalonitriles such as 1,3-bis(2′,3′-dicyanophenoxy)-2,2-dipentylpropane, 1,3-bis(2′,3′-dicyanophenoxy)-2,2-diethylpropane, 1,3-bis(2′,3′-dicyanophenoxy)-2,2-dioctylpropane, and 1,3-bis(2′,3′-dicyanophenoxy)-2-methyl-2-trityloxymethylpropane all gave bis-crown-like 1,11,15,25-tetrasubstituted phthalocyanines as pure compounds when treated with lithium octoxide in

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6

Postigo, Al, and Roberto A. Rossi. "A Novel Type of Nucleophilic Substitution Reactions on Nonactivated Aromatic Compounds and Benzene Itself with Trimethylsiliconide Anions." Organic Letters 3, no. 8 (2001): 1197–200. http://dx.doi.org/10.1021/ol015666s.

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7

Beier, Petr, Tereza Pastýříková, and George Iakobson. "Preparation of SF5Aromatics by Vicarious Nucleophilic Substitution Reactions of Nitro(pentafluorosulfanyl)benzenes with Carbanions." Journal of Organic Chemistry 76, no. 11 (2011): 4781–86. http://dx.doi.org/10.1021/jo200618p.

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8

Zhao, Zhensheng, Islam Jameel, and Graham K. Murphy. "Vicinal Dichlorination of o-Vinylbiphenyls and the Synthesis of 9-(Arylmethyl)fluorenes via Tandem Friedel–Crafts Alkylations." Synthesis 51, no. 13 (2019): 2648–59. http://dx.doi.org/10.1055/s-0037-1611562.

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Reacting ortho-vinylbiphenyls with (dichloroiodo)benzene (PhICl2) gives vicinal dichlorides, rapidly, and in excellent yield at room temperature. Treating the vic-dichlorides with 50 mol% AlCl3 in the presence of arene nucleophiles results in sequential intramolecular and intermolecular Friedel–Crafts alkylations to generate 9-(arylmethyl)fluorene derivatives. The dichlorination and alkylation reactions are operationally simple and tolerant of a variety of functional groups and substitution patterns, and give the products in moderate to excellent yield.

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9

Sekiguchi, Shizen, Hiromi Ishikura, Yukitoshi Hirosawa, and Nobuyuki Ono. "Aromatic nucleophilic substitution reactions of 1-dialkylamino-substituted activated benzenes with various amines in dimethyl sulfoxide." Tetrahedron 46, no. 16 (1990): 5567–78. http://dx.doi.org/10.1016/s0040-4020(01)87755-3.

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10

Beier, Petr, Tereza Pastyrikova, and George Iakobson. "ChemInform Abstract: Preparation of SF5Aromatics by Vicarious Nucleophilic Substitution Reactions of Nitro(pentafluorosulfanyl)benzenes with Carbanions." ChemInform 42, no. 38 (2011): no. http://dx.doi.org/10.1002/chin.201138043.

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11

Ćoćić, Dušan, Snežana Jovanović-Stević, Ratomir Jelić, et al. "Homo- and hetero-dinuclear Pt(ii)/Pd(ii) complexes: studies of hydrolysis, nucleophilic substitution reactions, DNA/BSA interactions, DFT calculations, molecular docking and cytotoxic activity." Dalton Transactions 49, no. 41 (2020): 14411–31. http://dx.doi.org/10.1039/d0dt02906h.

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Dinuclear complexes [Pd<sub>2</sub>(tpbd)Cl<sub>2</sub>]Cl<sub>2</sub>, [Pt<sub>2</sub>(tpbd)Cl<sub>2</sub>]Cl<sub>2</sub> and [PdPt(tpbd)Cl<sub>2</sub>]Cl<sub>2</sub> (tpbd = N,N,N′,N′-tetrakis(2-pyridylmethyl)benzene-1,4-diamine) have been synthesized and the kinetic, interactions with DNA/BSA and cytotoxic activity were studied.

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12

Banjoko, Olayinka, and Ibitola A. Babatunde. "Catalytic effects of hydrogen-bond acceptor solvent on nucleophilic aromatic substitution reactions in non-polar aprotic solvent: reactions of phenyl 2,4,6-trinitrophenyl ether with amines in benzene–acetonitrile mixtures." Tetrahedron 61, no. 33 (2005): 8035–40. http://dx.doi.org/10.1016/j.tet.2005.06.009.

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13

Fathalla, Magda F., and Ezzat A. Hamed. "Kinetics of the nucleophilic substitution reactions of methyl 2,4-dichloro-3,5-dinitrobenzoate with piperidine, piperazine, morpholine and thiomorpholine in methanol and benzene." Journal of Chemical Research 2006, no. 7 (2006): 413–16. http://dx.doi.org/10.3184/030823406777980646.

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14

Acosta Quintero, Lina M., Alirio Palma, Justo Cobo, and Christopher Glidewell. "Six polycyclic pyrimidoazepine derivatives: syntheses, molecular structures and supramolecular assembly." Acta Crystallographica Section C Structural Chemistry 72, no. 4 (2016): 346–57. http://dx.doi.org/10.1107/s2053229616004654.

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A versatile synthetic method has been developed for the formation of variously substituted polycyclic pyrimidoazepine derivatives, formed by nucleophilic substitution reactions on the corresponding chloro-substituted compounds; the reactions can be promoted either by conventional heating in basic solutions or by microwave heating in solvent-free systems. Thus, (6RS)-6,11-dimethyl-3,5,6,11-tetrahydro-4H-benzo[b]pyrimido[5,4-f]azepin-4-one, C14H15N3O, (I), was isolated from a solution containing (6RS)-4-chloro-8-hydroxy-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine and benzene-1,2

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15

Hong, Fung-E., Jenn-Woei Liaw, Bae-Jiunn Chien та ін. "Nucleophilic substitution reactions of acetylides on substituted tricarbonyl(η6-fluoroarene)chromium and reactions of tricarbonyl[η6-(2-trimethylsilylethynyl)toluene]chromium and tricarbonyl[η6-(p-ethynyl-phenylethynyl)benzene]chromium with dicobalt octacarbonyl". Polyhedron 18, № 21 (1999): 2737–47. http://dx.doi.org/10.1016/s0277-5387(99)00186-2.

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16

Medjdoub, Lahouaria, and Belbachir Mohammed. "New Method for Nucleophilic Substitution on Hexachlorocyclotriphosphazene by Allylamine Using an Algerian Proton Exchanged Montmorillonite Clay (Maghnite-H+) as a Green Solid Catalyst." Bulletin of Chemical Reaction Engineering & Catalysis 11, no. 2 (2016): 151. http://dx.doi.org/10.9767/bcrec.11.2.541.151-160.

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<p>Nucleophilic substitution on hexachlorocyclotriphosphazene (HCCTP) with allylamine in order to give hexa(allylamino)cyclotriphosphazene (HACTP) is performed for the first time under mild conditions by using diethylether as solvent to replace benzene which is very toxic. The reaction time is reduced to half and also performed at room temperature but especially in the presence of an eco-catalyst called Maghnite-H<sup>+</sup>. This catalyst has a significant role in the industrial scale. In fact, the use of Maghnite is preferred for its many advantages: a very low purchase pr

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17

Bhuvaneshwari, D. S., and K. P. Elango. "Solvent hydrogen bonding and structural effects on nucleophilic substitution reactions: Part 3. Reaction of benzenesulfonyl chloride with anilines in benzene/propan-2-ol mixtures." International Journal of Chemical Kinetics 39, no. 12 (2007): 657–63. http://dx.doi.org/10.1002/kin.20275.

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18

Arnone, Caterina, Giovanni Consiglio, Domenico Spinelli, and Vincenzo Frenna. "Catalysis in aromatic nucleophilic substitution. Part 9. Kinetics of the reactions of 2-bromo-3,5-dinitrothiohene with some meta- and para-substituted anilines in benzene." Journal of the Chemical Society, Perkin Transactions 2, no. 12 (1990): 2153. http://dx.doi.org/10.1039/p29900002153.

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19

Banjoko, Olayinka, and Ibitola A. Babatunde. "Rationalization of the conflicting effects of hydrogen bond donor solvent on nucleophilic aromatic substitution reactions in non-polar aprotic solvent: reactions of phenyl 2,4,6-trinitrophenyl ether with primary and secondary amines in benzene–methanol mixtures." Tetrahedron 60, no. 21 (2004): 4645–54. http://dx.doi.org/10.1016/j.tet.2004.03.079.

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20

ARNONE, C., G. CONSIGLIO, D. SPINELLI, and V. FRENNA. "ChemInform Abstract: Catalysis in Aromatic Nucleophilic Substitution. Part 9. Kinetics of the Reactions of 2-Bromo-3,5-dinitrothiophene with Some meta- and para- Substituted Anilines in Benzene." ChemInform 22, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199111057.

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21

Crampton, Michael R., та Simon D. Lord. "Kinetic and equilibrium studies of σ-adduct formation and nucleophilic substitution in the reactions of trinitro-activated benzenes with aliphatic amines in acetonitrile". Journal of the Chemical Society, Perkin Transactions 2, № 2 (1997): 369–76. http://dx.doi.org/10.1039/a603707k.

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22

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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23

Consiglio, Giovanni, Vincenzo Frenna, Elisabetta Mezzina, Antonio Pizzolato, and Domenico Spinelli. "Catalysis in aromatic nucleophilic substitution. Part 12.1 Kinetics of the reactions of some 2-phenoxy- and 2-( p-nitrophenoxy)-3-nitro-5-X-thiophenes with benzylamine and N-benzylmethylamine in benzene." Journal of the Chemical Society, Perkin Transactions 2, no. 2 (1998): 325–34. http://dx.doi.org/10.1039/a705667b.

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24

Hong, Fung-E., Shih-Chun Lo, Ming-Woei Liou, Lung-Fang Chou та Chu-Chieh Lin. "Nucleophilic substitution reactions of (η6-fluorotoluene)Cr(CO)3 and (η6-fluoroanisole)Cr(CO)3 toward phenylacetylide, fluorenyl, indolinyl and carbazolinyl lithium: crystal structures of tricarbonyl[η6-(1,2-diphenylethynyl)benzene]chromium and tricarbonyl[η6-(1,4-fluorenyl)toluene]chromium". Journal of Organometallic Chemistry 516, № 1-2 (1996): 123–31. http://dx.doi.org/10.1016/0022-328x(96)06131-1.

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25

Iakobson, George, and Petr Beier. "Highly selective synthesis of (E)-alkenyl-(pentafluorosulfanyl)benzenes through Horner–Wadsworth–Emmons reaction." Beilstein Journal of Organic Chemistry 8 (July 25, 2012): 1185–90. http://dx.doi.org/10.3762/bjoc.8.131.

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Diethyl 2-nitro-(pentafluorosulfanyl)benzylphosphonates, available by the vicarious nucleophilic substitution reaction of meta- and para-nitro-(pentafluorosulfanyl)benzenes and diethyl chloromethylphosphonate, undergo Horner–Wadsworth–Emmons reaction with aldehydes in the presence of potassium hydroxide in acetonitrile at ambient temperature to give (E)-2-nitro-1-alkenyl-(pentafluorosulfanyl)benzenes in good yields and high stereoselectivities. Follow-up transformations of the primary products provided (E)-1-alkenyl-(pentafluorosulfanyl)benzenes and 2-(2-arylethyl)-(pentafluorosulfanyl)aniline

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26

ARNONE, C., G. CONSIGLIO, V. FRENNA, E. MEZZINA, and D. SPINELLI. "ChemInform Abstract: Catalysis in Aromatic Nucleophilic Substitution. Part 11. Electronic Effects of a para-Like Methyl Group in the Reactions of 2-Bromo- and 2- Methoxy-5-methyl-3-nitrothiophene with Pyrrolidine and Piperidine in Methanol and in Benzene." ChemInform 25, no. 10 (2010): no. http://dx.doi.org/10.1002/chin.199410081.

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27

Guo, Cai-yun, Robert L. Kirchmeier, and Jean'ne M. Shreeve. "Nucleophilic substitution reactions of polyfluoroalkylsulfonamides." Journal of Fluorine Chemistry 52, no. 1 (1991): 29–36. http://dx.doi.org/10.1016/s0022-1139(00)80319-x.

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28

Vogel, Philip, Sarah Figueira, Sivaramakrishnan Muthukrishnan, and James Mack. "Environmentally benign nucleophilic substitution reactions." Tetrahedron Letters 50, no. 1 (2009): 55–56. http://dx.doi.org/10.1016/j.tetlet.2008.10.079.

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29

Rohrbach, Simon, Andrew J. Smith, Jia Hao Pang, et al. "Concerted Nucleophilic Aromatic Substitution Reactions." Angewandte Chemie International Edition 58, no. 46 (2019): 16368–88. http://dx.doi.org/10.1002/anie.201902216.

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30

Domingo, Luis R., Mar Ríos-Gutiérrez, Eduardo Chamorro, and Patricia Pérez. "Are one-step aromatic nucleophilic substitutions of non-activated benzenes concerted processes?" Organic & Biomolecular Chemistry 17, no. 35 (2019): 8185–93. http://dx.doi.org/10.1039/c9ob01589b.

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Analysis of the mechanism of one-step S<sub>N</sub>Ar reactions of non-activated benzenes shows the presence of structures similar to those of Meisenheimer intermediates, thus accounting for the non-concerted nature of these reactions.

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31

Ameri, Aliakbar Muhamdi. "Principles of Nucleophilic Substitution." American International Journal of Cancer Studies 1, no. 1 (2019): 11–18. http://dx.doi.org/10.46545/aijcs.v1i1.48.

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The work reported in this theoretical paper deals with types of substitution reaction ( sn1 , sn2 , conditions of both reactions , methods of both reactions , diagram of reactions , energy for reactions, types of reactants , products, rate of reactions , steps of reactions, transition state for reaction) and other reactions.

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32

Shen, Shusu. "Nucleophilic Substitution Reactions at Vinylic Carbons." Chinese Journal of Organic Chemistry 34, no. 12 (2014): 2448. http://dx.doi.org/10.6023/cjoc201406046.

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33

Rossi, Roberto A., Adriana B. Pierini, and Alicia B. Peñéñory. "Nucleophilic Substitution Reactions by Electron Transfer." Chemical Reviews 103, no. 1 (2003): 71–168. http://dx.doi.org/10.1021/cr960134o.

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34

Yew, Kyoung Han, Han Joong Koh, Hai Whang Lee, and Ikchoon Lee. "Nucleophilic substitution reactions of phenyl chloroformates." Journal of the Chemical Society, Perkin Transactions 2, no. 12 (1995): 2263. http://dx.doi.org/10.1039/p29950002263.

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35

Lennon, Patrick J., David P. Mack, and Quentin E. Thompson. "Nucleophilic catalysis of organosilicon substitution reactions." Organometallics 8, no. 4 (1989): 1121–22. http://dx.doi.org/10.1021/om00106a043.

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36

McGeary, Ross P., Sara Rasoul Amini, Vincent W. S. Tang, and Istvan Toth. "Nucleophilic Substitution Reactions of Pyranose Polytosylates." Journal of Organic Chemistry 69, no. 8 (2004): 2727–30. http://dx.doi.org/10.1021/jo035779k.

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37

Tatke, D. R., and S. Seshadrif. "Nucleophilic substitution reactions of azabenzanthrone derivatives." Dyes and Pigments 7, no. 2 (1986): 153–58. http://dx.doi.org/10.1016/0143-7208(86)85005-7.

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38

Moiseev, I. K., E. I. Bagrii, Yu N. Klimochkin, T. N. Dolgopolova, M. N. Zemtsova, and P. L. Trakhtenberg. "Adamantanol nitrates in nucleophilic substitution reactions." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 34, no. 9 (1985): 1983–85. http://dx.doi.org/10.1007/bf00953951.

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39

Zinad, Dhafer, Dunya AL-Duhaidahaw, Ahmed Al-Amiery, and Abdul Kadhum. "N-[4-(1-Methyl-1H-imidazol-2-yl)-2,4′-bipyridin-2′-yl]benzene-1,4-diamine." Molbank 2018, no. 4 (2018): M1030. http://dx.doi.org/10.3390/m1030.

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N-[4-(1-Methyl-1H-imidazol-2-yl)-2,4′-bipyridin-2′-yl]benzene-1,4-diamine was synthesized with a good yield by the reaction of 2′-chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine with 4-phenylenediamine. The functionalization of the pyridine was accomplished by a nucleophilic aromatic substitution (SNAr) reaction that afforded the target compound. The synthesized compound was characterized by chemical analysis, which includes nuclear magnetic resonance (NMR) (1H-NMR and 13C-NMR), Thin Layer Chromatography-Mass Spectrometry (TLC-MS), high- performance liquid chromatography (HPLC), Gas Chrom

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40

Feng, Shouai, Yixin Li, Hong Liu, et al. "Mesoporous Silica for Triphase Nucleophilic Substitution Reactions." CHIMIA International Journal for Chemistry 72, no. 7 (2018): 514–17. http://dx.doi.org/10.2533/chimia.2018.514.

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41

Rossi, Roberto, and Al Postigo. "Recent Advances on Radical Nucleophilic Substitution Reactions." Current Organic Chemistry 7, no. 8 (2003): 747–69. http://dx.doi.org/10.2174/1385272033486729.

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42

Barrett, Anthony G. M., D. Christopher Braddock, Rachel A. James, Nobuyuki Koike, and Panayiotis A. Procopiou. "Nucleophilic Substitution Reactions of (Alkoxymethylene)dimethylammonium Chloride." Journal of Organic Chemistry 63, no. 18 (1998): 6273–80. http://dx.doi.org/10.1021/jo980583j.

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43

Matveeva, E. D., T. A. Podrugina, Yu K. Grishin, A. S. Pavlova, and N. S. Zefirov. "Phosphonium-iodonim ylides in nucleophilic substitution reactions." Russian Journal of Organic Chemistry 43, no. 2 (2007): 201–6. http://dx.doi.org/10.1134/s107042800702008x.

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44

GUO, C. Y., R. L. KIRCHMEIER, and J. M. SHREEVE. "ChemInform Abstract: Nucleophilic Substitution Reactions of Polyfluoroalkylsulfonamides." ChemInform 23, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199203088.

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45

Żwawiak, Justyna, and Lucjusz Zaprutko. "Reactions of Nucleophilic Substitution in Bicyclic Nitroimidazodihydrooxazoles." Journal of Heterocyclic Chemistry 51, no. 5 (2014): 1463–67. http://dx.doi.org/10.1002/jhet.1907.

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46

Narasaka, Koichi, Shunsuke Chiba, and Kaori Ando. "Concerted Nucleophilic Substitution Reactions at Vinylic Carbons." Synlett 2009, no. 16 (2009): 2549–64. http://dx.doi.org/10.1055/s-0029-1217752.

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47

Guidotti, Jérôme, Vincent Schanen, Marc Tordeux, and Claude Wakselman. "Reactions of (chlorodifluoromethyl)benzene and (chlorodifluoromethoxy)benzene with nucleophilic reagents." Journal of Fluorine Chemistry 126, no. 4 (2005): 443–47. http://dx.doi.org/10.1016/j.jfluchem.2004.10.001.

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48

Marques, H. M. "Nucleophilic participation in ligand substitution reactions of aquocobalamin: Reactions with imidazoles." Journal of Inorganic Biochemistry 36, no. 3-4 (1989): 194. http://dx.doi.org/10.1016/0162-0134(89)84143-1.

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49

Beddoe, Rhydian H., Keith G. Andrews, Valentin Magné, et al. "Redox-neutral organocatalytic Mitsunobu reactions." Science 365, no. 6456 (2019): 910–14. http://dx.doi.org/10.1126/science.aax3353.

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Nucleophilic substitution reactions of alcohols are among the most fundamental and strategically important transformations in organic chemistry. For over half a century, these reactions have been achieved by using stoichiometric, and often hazardous, reagents to activate the otherwise unreactive alcohols. Here, we demonstrate that a specially designed phosphine oxide promotes nucleophilic substitution reactions of primary and secondary alcohols in a redox-neutral catalysis manifold that produces water as the sole by-product. The scope of the catalytic coupling process encompasses a range of ac

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50

Charushin, Valery N., and Oleg N. Chupakhin. "Nucleophilic aromatic substitution of hydrogen and related reactions." Mendeleev Communications 17, no. 5 (2007): 249–54. http://dx.doi.org/10.1016/j.mencom.2007.09.001.

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