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Journal articles on the topic 'Mechanism of aromatic substitution reactions'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Mąkosza, Mieczysław. "How Does Nucleophilic Aromatic Substitution in Nitroarenes Really Proceed: General Mechanism." Synthesis 49, no. 15 (2017): 3247–54. http://dx.doi.org/10.1055/s-0036-1588444.

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On the basis of previously published experimental studies and ab initio calculations, a general corrected mechanism of nucleophilic aromatic substitution was formulated. It was shown that conventional nucleophilic substitution of halogens is a slow secondary reaction whereas nucleophilic substitution of hydrogen is the fast primary process. The general mechanism embraces both of these alternative and complementary reactions.

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2

Harsanyi, MC, PA Lay, RK Norris, and PK Witting. "Substitution of Bridgehead Halogens by a Free-Radical Electron-Transfer Mechanism." Australian Journal of Chemistry 49, no. 5 (1996): 581. http://dx.doi.org/10.1071/ch9960581.

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The reactions of 1-bromo-7-nitro- and 1-bromo-6-nitro-1,4-methanonaphthalene (2) and (3), and 9-bromo-2-nitro, 10-bromo-2-nitro-, 9,10-dibromo-2-nitro- and 9,10-diiodo-2-nitro-9,10-ethano-9,10-dihydroanthracene (4)-(7). respectively, with the sodium salt (1) of p-toluenethiol gave substitution products that were shown to be formed by an SRN1 or a related radical chain mechanism. In the relatively slow substitution reactions of the salt (1) with compounds (2)-(5). That contain bromine at bridgehead positions that are either meta- or para-benzylic to an aromatic nitro group, the rates of substit

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3

Gazitúa, Marcela, Ricardo A. Tapia, Renato Contreras, and Paola R. Campodónico. "Mechanistic pathways of aromatic nucleophilic substitution in conventional solvents and ionic liquids." New J. Chem. 38, no. 6 (2014): 2611–18. http://dx.doi.org/10.1039/c4nj00130c.

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4

Prins, H. J. "The mechanism of substitution reactions in the aromatic nucleus." Recueil des Travaux Chimiques des Pays-Bas 44, no. 2 (2010): 166–72. http://dx.doi.org/10.1002/recl.19250440212.

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5

Dmitrieva, A., and A. Stepacheva. "Friedel-Krafts alkylation." Bulletin of Science and Practice, no. 8 (August 15, 2017): 43–48. https://doi.org/10.5281/zenodo.842942.

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The mechanism of the reaction of alkylation of aromatic compounds according to Friedel–Crafts is considered. Unlike the acylation reaction, alkylation is a reversible process. The general principle of the reaction is the intermediate formation of carbenium ions capable of reacting as an electrophile in the aromatic reactions of electrophilic substitution. It is established that the mechanism of this reaction is ensured by the detection of the σ–complex at low temperatures. The possibility of using the intramolecular variant of Friedel–Crafts alkylation is considered; li

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6

Elias, Gracy, Bruce J. Mincher, Stephen P. Mezyk, Thomas D. Cullen, and Leigh R. Martin. "Anisole nitration during gamma-irradiation of aqueous nitrite and nitrate solutions: free radical versus ionic mechanisms." Environmental Chemistry 7, no. 2 (2010): 183. http://dx.doi.org/10.1071/en09109.

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Environmental context. The nitration of aromatic compounds is an important source of toxic, carcinogenic, and mutagenic species in the atmosphere. Gas phase nitration typically occurs by free radical reactions. Condensed-phase free radical reactions may also be relevant in fog and cloud water in polluted areas, in urban aerosols with low pH, in water treatment using advanced oxidation processes such as e-beam irradiation, and in nuclear waste treatment applications. This paper discusses research towards an improved understanding of nitration of aromatic compounds in the condensed phase under c

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7

Kinzel, Daniel, Shmuel Zilberg, and Leticia González. "Gas-phase electrophilic aromatic substitution mechanism with strong electrophiles explained by ab initio non-adiabatic dynamics." Phys. Chem. Chem. Phys. 16, no. 35 (2014): 18686–89. http://dx.doi.org/10.1039/c4cp01456a.

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8

de Barry Barnett, Edward, and James Wilfred Cook. "Note on the mechanism of substitution reactions in the aromatic nucleus." Recueil des Travaux Chimiques des Pays-Bas 43, no. 4 (2010): 262–65. http://dx.doi.org/10.1002/recl.19240430405.

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9

de Barry Barnett, Edward, and Marcus A. Matthews. "The mechanism of substitution reactions in the aromatic nucleus. Part I." Recueil des Travaux Chimiques des Pays-Bas 43, no. 8 (2010): 530–41. http://dx.doi.org/10.1002/recl.19240430803.

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10

de Barry Barnett, Edward, and James Wilfred Cook. "Note on the mechanism of substitution reactions in the aromatic nucleus." Recueil des Travaux Chimiques des Pays-Bas 43, no. 12 (2010): 897–98. http://dx.doi.org/10.1002/recl.19240431209.

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11

de Barry Barnett, Edward, James Wilfred Cook, and Marcus Aurelius Matthews. "The mechanism of substitution reactions in the aromatic nucleus. Part III." Recueil des Travaux Chimiques des Pays-Bas 44, no. 8 (2010): 728–39. http://dx.doi.org/10.1002/recl.19250440807.

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12

de Barry Barnett, Edward, James Wilfred Cook, and Marcus Aurelius Matthews. "The mechanism of substitution reactions in the aromatic nucleus. Part IV." Recueil des Travaux Chimiques des Pays-Bas 44, no. 9 (2010): 818–26. http://dx.doi.org/10.1002/recl.19250440914.

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13

de Barry Barnett, Edward, James Wilfred Cook, and Marcus Aurelius Matthews. "The mechanism of substitution reactions in the aromatic nucleus. Part V." Recueil des Travaux Chimiques des Pays-Bas 44, no. 10 (2010): 894–99. http://dx.doi.org/10.1002/recl.19250441010.

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14

de Barry Barnett, E., M. A. Matthews, and J. L. Wiltshire. "The mechanism of substitution reactions in the aromatic nucleus. Part VII." Recueil des Travaux Chimiques des Pays-Bas 45, no. 8 (2010): 558–63. http://dx.doi.org/10.1002/recl.19260450805.

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15

Tanaka, Kiyoshi, Makoto Deguchi, and Satoru Iwata. "Ab initio Study of Nucleophilic Aromatic Substitution of Polyfluorobenzene." Journal of Chemical Research 23, no. 9 (1999): 528–29. http://dx.doi.org/10.1177/174751989902300905.

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Calculations at ab initio levels of theory of the nucleophilic aromatic substitution of pentafluoronitrobenzene with amines demonstrate an addition–elimination mechanism (SNAr), with the rate-determining step at the second transition state involving C–F bond breaking, and support the ortho-selectivity of the reactions based on the stability of the second transition states.

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16

Cao, Liwei, Mikhail Kabeshov, Steven V. Ley, and Alexei A. Lapkin. "In silico rationalisation of selectivity and reactivity in Pd-catalysed C–H activation reactions." Beilstein Journal of Organic Chemistry 16 (June 25, 2020): 1465–75. http://dx.doi.org/10.3762/bjoc.16.122.

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A computational approach has been developed to automatically generate and analyse the structures of the intermediates of palladium-catalysed carbon–hydrogen (C–H) activation reactions as well as to predict the final products. Implemented as a high-performance computing cluster tool, it has been shown to correctly choose the mechanism and rationalise regioselectivity of chosen examples from open literature reports. The developed methodology is capable of predicting reactivity of various substrates by differentiation between two major mechanisms – proton abstraction and electrophilic aromatic su

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17

Bakke, J. M. "Nitropyridines: Synthesis and reactions." Pure and Applied Chemistry 75, no. 10 (2003): 1403–15. http://dx.doi.org/10.1351/pac200375101403.

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Reaction of pyridine and substituted pyridines with N2O5 in an organic solvent gives the N-nitropyridinium ion. When this is reacted with SO2/HSO3– in water, 3-nitropyridine is obtained (77 % yield). With substituted pyridines, the method gives good yields for 4-substituted and moderate yields for 3-substituted pyridines. The reaction mechanism is not an electrophilic aromatic substitution, but one in which the nitro group migrates from the 1-position to the 3-position by a [1,5 ] sigmatropic shift. From 4-aminopyridine, imi- dazo [4,5-c ] pyridines have been synthesized. From 3-nitropyridine,

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18

Šket, Boris, Marko Zupan, Nataša Zupančič, and Barbara Pahor. "Photosubstitution reactions on aromatic and heteroaromatic rings evidence for addition and substitution mechanism." Tetrahedron 47, no. 27 (1991): 5029–42. http://dx.doi.org/10.1016/s0040-4020(01)80966-2.

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19

Domingo, Luis R., María José Aurell, and Mar Ríos-Gutiérrez. "A Molecular Electron Density Theory Study of the Domino Reaction of N-Phenyl Iminoboranes with Benzaldehyde Yielding Fused Bicyclic Compounds." Molecules 28, no. 17 (2023): 6211. http://dx.doi.org/10.3390/molecules28176211.

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The reaction of N-phenyl iminoborane with benzaldehyde yielding a fused aromatic compound, recently reported by Liu et al., has been studied within the Molecular Electron Density Theory (MEDT). Formation of the fused aromatic compound is a domino process that comprises three consecutive reactions: (i) formation of a weak molecular complex between the reagents; (ii) an intramolecular electrophilic attack of the activated carbonyl carbon of benzaldehyde on the ortho position of the N-phenyl substituent of iminoborane; and (iii) a formal 1,3-hydrogen shift yielding the final fused aromatic compou

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20

Chavan, Arun B., Sanjeev M. Reddy, and G. Krishna Chaitanya. "Elucidating Reaction Mechanism of Gefitinib- An Anticancer Drug by Computational Technique." Oriental Journal Of Chemistry 40, no. 3 (2024): 835–40. http://dx.doi.org/10.13005/ojc/400327.

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The present investigation centres on the application of quantum chemistry to clarify the innovative synthetic pathway for Gefitinib derived from methyl 2-isocyano-4,5-dimethoxybenzoate. This pathway encompasses various chemical reactions such as cyclization, halogenation, regioselective demethylation, Williamson's ether synthesis, and nucleophilic aromatic substitution. The reaction necessitates the presence of four intermediate species and yields a total of 11 transition states [TS]. The energies of each reactant, intermediate, and product were determined through the utilisation of density fu

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21

Ibrahim, Mahmoud F., Hanaa A. Abdel-Reheem, and Ezzat A. Hamed. "NUCLEOPHILIC SUBSTITUTION REACTIONS OF 2, 4-DINITTROPHENYL ACETATE WITH HYDRAZINE AND METHANOL SOLVENT EFFECT." EPH - International Journal of Applied Science 6, no. 1 (2020): 23–26. http://dx.doi.org/10.53555/eijas.v6i1.106.

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The generally accepted mechanism for nucleophilic aromatic substitution (the snare mechanism) is an addition-elimination mechanism and involves the formation of a Meisenheimer type of intermediate. The hydrazinolysis of 2,4-dinitrophenyl acetate in methanol proceeds exclusively through acyl-oxygen scission by a concerted mechanism. The process depends on the basicity of the leaving group and its steric hindrance as well as the possible intramolecular hydrogen bond in the transition state. The reactions of 2,4Dinittrophenyl Acetate with hydrazine obeyed pseudo-first-order rate constants (kobs).

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22

McLure, FI, and RK Norris. "The Stereochemistry of SRN1 Reactions in Nitroacenaphthenes." Australian Journal of Chemistry 40, no. 3 (1987): 523. http://dx.doi.org/10.1071/ch9870523.

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The reaction of the 2-chloro-1,l-dialkyl-6-nitroacenaphthenes (1)-(3) with azide and p- toluenethiolate ions takes place by the SRN1 mechanism, to give the substitution products (27)-(32), despite the fact that the nitro group and the chlorine-bearing benzylic carbon are attached to different aromatic rings. The reaction of the stereoisomers (2) and (3) of 2-chloro-1-ethyl-1-methyl-6-nitroacenaphthene takes place through an effectively planar benzylic radical (35), which is preferentially attacked from the face remote from the a-ethyl group. The presence of geminal alkyl groups α to the reacti

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23

Lee, Eunsung, and Ewa Pietrasiak. "Activation of C–F, Si–F, and S–F Bonds by N-Heterocyclic Carbenes and Their Isoelectronic Analogues." Synlett 31, no. 14 (2020): 1349–60. http://dx.doi.org/10.1055/s-0040-1707106.

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Reactions involving C–F, Si–F, and S–F bond cleavage with N-heterocyclic carbenes and isoelectronic species are reviewed. Most examples involve activation of aromatic C–F bond via an SNAr pathway and nucleophilic substitution of fluorine in electron-deficient olefins. The mechanism of the C–F bond activation depends on the reaction partners and the reaction can proceed via addition–elimination, oxidative addition (concerted or stepwise) or metathesis. The adducts formed upon substitution find applications in organic synthesis, as ligands and as stable radical precursors, but in most cases, the

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24

Sharma, Nishant, Rupayan Biswas, and Upakarasamy Lourderaj. "Dynamics of a gas-phase SNAr reaction: non-concerted mechanism despite the Meisenheimer complex being a transition state." Physical Chemistry Chemical Physics 22, no. 45 (2020): 26562–67. http://dx.doi.org/10.1039/d0cp05567k.

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25

Shakhmurzova, Kamila T., Zhanna I. Kurdanova, Azamat Zhansitov, Marina Balagova, and Svetlana Khashirova. "Synthesis of Aromatic Polyether Ketones by Electrophilic Substitution." Key Engineering Materials 869 (October 2020): 456–65. http://dx.doi.org/10.4028/www.scientific.net/kem.869.456.

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This article presents a scientific review of the literature on the production of polyether ketones and copolymers of various structures with a complex of valuable properties. Particular attention is paid to the synthesis of polyether ketones by electrophilic substitution by the Friedel-Crafts reaction mechanism.

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26

Akinyele, Elizabeth T., Ikenna Onyido, and J. Hirst. "Mechanisms of aromatic nucleophilic substitution reactions in ethyl acetate and tetrahydrofuran." Journal of Physical Organic Chemistry 3, no. 1 (1990): 41–47. http://dx.doi.org/10.1002/poc.610030109.

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27

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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28

SKET, B., M. ZUPAN, N. ZUPANCIC, and B. PAHOR. "ChemInform Abstract: Photosubstitution Reactions on Aromatic and Heteroaromatic Rings. Evidence for Addition and Substitution Mechanism." ChemInform 22, no. 41 (2010): no. http://dx.doi.org/10.1002/chin.199141071.

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29

Galli, Carlo, and Silvia Di Giammarino. "Studies of substrate selectivity in aromatic iodination and other substitution reactions reinforce previous conclusions about the nature of the mechanism of electrophilic aromatic substitutions." Journal of the Chemical Society, Perkin Transactions 2, no. 6 (1994): 1261. http://dx.doi.org/10.1039/p29940001261.

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30

Zonozi, Fatemeh, Mehdi Pordel, S. Ali Beyramabadi, and Ali Morsali. "Theoretical Investigation on the Kinetics and Mechanism of the Synthesis of Fluorescent 3,8-Disubstituted-3H-Imidazo [4,5-a] Acridine-11-Carbonitriles." Progress in Reaction Kinetics and Mechanism 41, no. 4 (2016): 365–70. http://dx.doi.org/10.3184/146867816x14720534560565.

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3,8-Disubstituted-3H-imidazo[4,5-a]acridine-11-carbonitriles show very interesting optical properties. In some cases, they have higher quantum yields compared to well-known fluorescent dyes such as fluorescein. Hitherto, no detailed theoretical study has been reported on the mechanism of the synthesis of the titled compounds, hence an accurate and detailed theoretical investigation on the synthesis of these dyes is desirable. In this paper, density functional theory (DFT) methods have been employed to investigate the most reasonable mechanism in formation of these fluorophores. All species and

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31

Kochetova, Ludmila B., and Tatiana P. Kustova. "Kinetics and mechanism of acyl transfer reactions. Part 15. Quantumchemicalsimulation of mechanisms of reactions of N-ethylaniline sulfonation." Butlerov Communications 57, no. 2 (2019): 19–27. http://dx.doi.org/10.37952/roi-jbc-01/19-57-2-19.

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The RHF/6-31G(d) quantum chemical simulation of the mechanism of the interaction of the secondary fatty aromatic amine N-ethylaniline with benzenesulfonyl chloride under conditions of non-specific water solvation, using the continuum model of the solvent, as well as of sulfonylation reactions of N-ethylaniline solvation complexes containing one water molecule, modeled specific solvation of N-ethylaniline with water, and one molecule of water and one of dioxane, which simulate the solvation of the amine with aqueous dioxane. Three-dimensional potential energy surface of these processes is calcu

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32

Guerrero Zúñiga, Leonor Angélica, Ana Cristina Ramirez-Gallardo, Maria Fernanda López Sánchez, and Isidoro Garcia-Cruz. "Hydrodeoxygenation of anisole to produce value-added products: ortho-, meta-, para-cresol." Renewable energy, biomass & sustainability 7, no. 1 (2025): 11–21. https://doi.org/10.56845/rebs.v7i1.451.

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This work presents a detailed study on the trans-methylation reaction using density functional theory (DFT), an advanced computational technique for analyzing and predicting molecular-level interactions. Trans-methylation is a crucial step in both catalytic and non-catalytic decomposition of methoxybenzene (anisole), with a special focus on processes generating free radicals and methyl-type carbocations through the cleavage of the methyl group. The study highlights that, in the presence of Brønsted-acid catalysts (such as HZSM-5), trans-methylation follows a specific mechanism involving dual e

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33

Berthelot, Jacques, Catherine Guette, Paul-Louis Desbène, Jean-Jacques Basselier, Patrick Chaquin, and Daniel Masure. "Bromation régiosélective en série aromatique. I: Monobromation en position para de phénols et d'aminés aromatiques par le tribromure de tétrabutylammonium." Canadian Journal of Chemistry 67, no. 12 (1989): 2061–66. http://dx.doi.org/10.1139/v89-320.

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The reaction of tetrabutylammonium tribromide (TBABr3) with phenols and aromatic amines in aprotic and non-basic solvents at 20 °C gives exclusively the corresponding para-brominated compounds in high yields. A mechanism involving electrophilic substitution by the tribromide anion Br3− itself is suggested to account for the results, especially the regioselective para bromination. Keywords: bromination, tetrabutylammonium tribromide, phenols, aromatic amines.

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34

Engell, Karen M., Robert A. McClelland, and Poul E. Sørensen. "The decomposition of methyl hemiacetals of benzaldehyde in aqueous solution: a study of the effect of aromatic substitution." Canadian Journal of Chemistry 77, no. 5-6 (1999): 978–89. http://dx.doi.org/10.1139/v99-102.

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The acid-base catalysed decomposition of hydrates and hemiacetals of carbonyl compounds are classical examples of reactions where (slow) proton transfer is coupled with heavy atom reorganization, i.e., CO bond breaking and solvent reorganization. We have studied the influence of m- and p-substitution in the carbonyl electrophile on the kinetics of the acid and base catalysis of the decomposition of methyl hemiacetals of benzaldehyde. The experimental data are well described by three-dimensional More O'Ferrall - Jencks energy contour diagrams according to principles developed by Jencks (the BE

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35

Ji, Pengju, John H. Atherton, and Michael I. Page. "The Kinetics and Mechanisms of Aromatic Nucleophilic Substitution Reactions in Liquid Ammonia." Journal of Organic Chemistry 76, no. 9 (2011): 3286–95. http://dx.doi.org/10.1021/jo200170z.

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36

Sanecki, Przemyslaw, and Edward Rokaszewski. "Kinetics of hydrolysis of aromatic mono- and disulfonyl chlorides." Canadian Journal of Chemistry 65, no. 9 (1987): 2263–67. http://dx.doi.org/10.1139/v87-377.

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A continuous polarographic method of recording instantaneous concentrations of —SO2Cl groups in an aqueous acetic acid system containing CH3CO2Na has been elaborated. Ten model monosulfonyl chlorides underwent hydrolysis according to pseudo-first order kinetics (20% H2O, 80% v.v. CH3CO2H, 0.5 mol × dm−3 CH3CO2Na). Plots of hydrolysis for seven disulfonyl dichlorides with different number of —CH3 groups have been determined. Pseudo-first order rate constants for two consecutive reactions of hydrolysis (k1 and k2) have been computed and the influence of —SO2Cl and [Formula: see text] groups on t

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37

Osipov, Dmitry V., Kirill S. Korzhenko та Vitaly A. Osyanin. "Three-Component Condensation of β-Ketonitriles, 4-Fluorobenzaldehyde, and Secondary Cyclic Amines". Reactions 3, № 4 (2022): 625–33. http://dx.doi.org/10.3390/reactions3040042.

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A new three-component condensation of β-ketonitriles, 4-fluorobenzaldehyde, and secondary cyclic amines was developed. A possible reaction mechanism has been proposed including Knoevenagel condensation followed by aromatic nucleophilic substitution. It was found that in the case of 3-oxopropanenitrile bearing the 6-amino-1,3-dimethyluracil moiety, the reaction is not accompanied by fluorine substitution in the Knoevenagel adduct, and the Michael addition of a secondary amine occurs followed by oxidation.

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38

Majek, Michal, Fabiana Filace, and Axel Jacobi von Wangelin. "On the mechanism of photocatalytic reactions with eosin Y." Beilstein Journal of Organic Chemistry 10 (April 30, 2014): 981–89. http://dx.doi.org/10.3762/bjoc.10.97.

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A combined spectroscopic, synthetic, and apparative study has allowed a more detailed mechanistic rationalization of several recently reported eosin Y-catalyzed aromatic substitutions at arenediazonium salts. The operation of rapid acid–base equilibria, direct photolysis pathways, and radical chain reactions has been discussed on the basis of pH, solvent polarity, lamp type, absorption properties, and quantum yields. Determination of the latter proved to be an especially valuable tool for the distinction between radical chain and photocatalytic reactions.

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39

Chupakhin, Oleg N., and Valery N. Charushin. "Nucleophilic C–H functionalization of arenes: a new logic of organic synthesis." Pure and Applied Chemistry 89, no. 8 (2017): 1195–208. http://dx.doi.org/10.1515/pac-2017-0108.

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AbstractDirect metal-free C–H functionalization of arenes with nucleophiles is a new chapter in the chemistry of aromatics. Comprehensive studies on nucleophilic substitution of hydrogen in arenes (the SNH reactions), including mechanisms, intermediates, mathematic and electrochemical modeling, kinetics, electron-transfer, etc. have shown that this is not the hydride ion, but C–H proton is departed, and this process is facilitated by the presence of an appropriate oxidant or an auxiliary group. The SNH reactions, as a part of the general C–H functionalization concept, change the logic of organ

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40

Liu, Shiqi, Shuxun Sang, Tian Wang, Yi Du, Jinlong Jia, and Huihuang Fang. "The effects of CO2 on organic groups in bituminous coal and high-rank coal via Fourier transform infrared spectroscopy." Energy Exploration & Exploitation 36, no. 6 (2018): 1566–92. http://dx.doi.org/10.1177/0144598718764752.

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The interactions between supercritical CO2 and coal and their effects on changes in the coal pore structure and organic groups play a critical role in the CO2 geological storage-enhanced coalbed methane recovery. To investigate the effects of supercritical CO2 on organic groups in coals of different ranks and its mechanisms under different temperature and pressure conditions, CO2 sequestration processes in bituminous coals and high-rank coals were replicated using a high-pressure reactor. Four coal samples of different ranks were exposed to supercritical CO2 and water under three temperatures

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41

Yamato, Takehiko, Kiwamu Tokuhisa, and Hirohisa Tsuzuki. "Medium-sized cyclophanes. part 51. Acylation of [2.2]metaparacyclophanes: through-space electronic interactions between two benzene rings." Canadian Journal of Chemistry 78, no. 2 (2000): 238–47. http://dx.doi.org/10.1139/v00-006.

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The acylation of 8-methyl- (1b) and 8-methoxy[2.2]metaparacyclophane 1c with 1.1 equiv. of acetyl chloride in CS2 solution in the presence of aluminum chloride afforded 15-acetyl-8-methyl- (2b) and 12-acetyl-8-methoxy[2.2]metaparacyclophanes (3c) with 65 and 41% yields, respectively. The different orientations for the electrophilic substitution were observed to be dependant on the substituent at the 8 position. On the other hand, when the same reaction was carried out under the same reaction conditions with the corresponding 5-tert-butyl derivatives (11), ipso-acetylation at the tert-butyl gro

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42

Mazal, Ctibor, та Jaroslav Jonas. "Nucleophilic Vinylic Substitution on α-Tosyloxymethylene Lactones". Collection of Czechoslovak Chemical Communications 58, № 7 (1993): 1607–23. http://dx.doi.org/10.1135/cccc19931607.

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Sodium salt of 3-hydroxymethylenetetrahydro-2H-pyran-2-one (V), obtained by Claisen condensation of δ-valerolactone with ethyl formate, was converted into its sulfonates and carboxylates IV, VII - X, which were obtained either as pure E-isomers or as mixtures of E- and Z-isomers; the mixtures were chromatographically separated. Substitution reaction of α-tosyloxymethylene lactones II, III and IV with aromatic thiols, azide anion, secondary amines and sodium enolates XI, XII and V was studied. The stereochemical outcome of this substitution is discussed from the viewpoint of mechanism of nucleo

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43

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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44

Liang, Dingcheng, Deqian Liu, Shuai Yang, Changyu Lu, Qiang Xie, and Jinchang Liu. "Effects of Bromination-Dehydrobromination on the Microstructure of Isotropic Pitch Precursors for Carbon Fibers." Polymers 12, no. 12 (2020): 3059. http://dx.doi.org/10.3390/polym12123059.

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In this work, isotropic pitch precursors are synthesized by the bromination-debromination method with ethylene bottom oil (EO) as the raw material and bromine as the initiator for pitch formation and condensation reactions. The aggregation structure, molecular weight distribution, and molecular structure of isotropic pitch precursors are characterized by thermal mechanical analyzer (TMA), MALDI TOF-MS, and 13C NMR, respectively, for revealing the mechanism of synthesis of isotropic pitch precursors. The results show that at low bromine concentrations, polycyclic aromatic hydrocarbons (PAHs) we

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45

Masuya, Yoshihiro, Yuki Kawashima, Takuya Kodama, Naoto Chatani, and Mamoru Tobisu. "Thiolate-Initiated Synthesis of Dibenzothiophenes from 2,2′-Bis(methylthio)-1,1′-Biaryl Derivatives through Cleavage of Two Carbon–Sulfur Bonds." Synlett 30, no. 17 (2019): 1995–99. http://dx.doi.org/10.1055/s-0037-1611974.

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A catalytic reaction involving the cleavage of two carbon–sulfur bonds in 2,2′-bis(methylthio)-1,1′-biaryl derivatives is reported. This reaction does not require a transition-metal catalyst and is promoted by a thiolate anion. Notably, based on DFT calculations, the product-forming cyclization step is shown to proceed through a concerted nucleophilic aromatic substitution (CSNAr) mechanism.

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46

Duvauchelle, Valentin, David Bénimélis, Patrick Meffre та Zohra Benfodda. "Catalyst-Free Site Selective Hydroxyalkylation of 5-Phenylthiophen-2-amine with α-Trifluoromethyl Ketones through Electrophilic Aromatic Substitution". Molecules 27, № 3 (2022): 925. http://dx.doi.org/10.3390/molecules27030925.

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An original and effective approach for achieving trifluoromethyl hydroxyalkylation of 5-phenylthiophen-2-amine using α-trifluoromethyl ketones is described. In the last few years, reaction of Friedel-Crafts had been widely used to realize hydroxyalkylation on heterocycles such as indoles or thiophenes by means of Lewis acid as catalyst. Additionally, amine functions are rarely free when carbonyl reagents are used because of their tendency to form imines. This is the first time that a site-selective electrophilic aromatic substitution on C3 atom of an unprotected 5-phenylthiophen-2-amine moiety

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Emokpae, Thomas A., Patrick U. Uwakwe, and Jack Hirst. "The effect of ortho substituents on the mechanism of aromatic nucleophilic substitution reactions in dipolar aprotic solvents." Journal of the Chemical Society, Perkin Transactions 2, no. 1 (1993): 125. http://dx.doi.org/10.1039/p29930000125.

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Patskovsky, Yury, Larysa Patskovska, Steven C. Almo, and Irving Listowsky. "Transition State Model and Mechanism of Nucleophilic Aromatic Substitution Reactions Catalyzed by Human GlutathioneS-Transferase M1a-1a†." Biochemistry 45, no. 12 (2006): 3852–62. http://dx.doi.org/10.1021/bi051823+.

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Kochetova, Ludmila B., and Tatiana P. Kustova. "Kinetics and mechanism of acyl transfer reactions. Part 16. Quantum chemical simulation of mechanism of N-methylaniline sulfonation in aqueous 1,4-dioxane." Butlerov Communications 61, no. 1 (2020): 1–8. http://dx.doi.org/10.37952/roi-jbc-01/20-61-1-1.

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The RHF/6-31G(d) quantum chemical simulation of the mechanism of the secondary fatty aromatic amine N-methylaniline interaction with benzenesulfonyl chloride under conditions of N-methylaniline specific solvation by one water molecule and one 1,4-dioxane molecule, and under conditions of N-methylaniline specific solvation by two water molecules and one 1,4-dioxane molecule. Three-dimensional potential energy surfaces of the processes pointed out are computed. It is shown that in the both cases a single route of the reactions is realized, starting as an axial nucleophilic attack, which goes fur

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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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