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Dissertations / Theses on the topic 'Mechanism of aromatic substitution reactions'

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Published: 5 June 2025

Last updated: 1 August 2025

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1

Murphy, Nicholas Patrick. "Radical aromatic cyclisation and substitution reactions." Thesis, University of Warwick, 2008. http://wrap.warwick.ac.uk/2286/.

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This dissertation is divided into five chapters. Chapter One consists of an introduction to radical cyclisation and rearrangement reactions. Chapter Two investigates the reactions of substituted arylsulfonamides 278a-l with copper bromide and an amine ligand-TPA. This reaction involves an alkyl radical generated from the copper (I) bromide/TPA complex, which can then undergo a 1,5- ipso attack onto the sulfonamide leading to a cyclohexadienyl radical intermediate. Re-aromatisation and extrusion of sulfur dioxide leads to an amidyl radical intermediate. This can undergo either cyclisation back

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2

Liljenberg, Magnus. "Quantum Chemical Studies of Aromatic Substitution Reactions." Doctoral thesis, KTH, Tillämpad fysikalisk kemi, 2017. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-206964.

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In this thesis, density functional theory (DFT) is used to investigate the mechanisms and reactivities of electrophilic and nucleophilic aromatic substitution reactions (SEAr and SNAr respectively). For SEAr, the σ-complex intermediate is preceded by one (halogenation) or two (nitration) π-complex intermediates. Whereas the rate-determining transition state (TS) for nitration resembles the second π-complex, the corresponding chlorination TS is much closer to the σ-complex. The last step, the expulsion of the proton, is modeled with an explicit solvent molecule in combination with PCM and confi

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3

Martin, Peter Arnold. "Nucleophilic substitution reactions of some polyhalogenated compounds." Thesis, Durham University, 1987. http://etheses.dur.ac.uk/6876/.

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Rate measurements for the reactions of a series of polyfluoro - and polychloro - pyridines with aniline and ammonia in 60/40 dioxan/water at 25ºC has shown that chlorine, when ortho and para to the position of attack, is activating with respect to fluorine, but at the position meta to the point of attack, chlorine and fluorine are virtually equivalent in their effect on reaction rate. The trifluoromethyl and nitrile groups were found to be activating relative to fluorine when ortho and para to the position of substitution and the nitrile group was thus found to be ortho/para directing. The ort

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4

Roberts, S. D. "Regioselective electrophilic aromatic substitution reactions of naphthalene over solids." Thesis, Swansea University, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.638685.

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Chapter 1 highlights the many advantages of heterogeneous inorganic solids as catalysts, and summarises the various microporous and mesoporous solids that have been employed as catalysts. The synthesis and characterisation of the mesoporous materials that were used in the study are described. Chapter 2 focuses on the nitration of naphthalene. An introduction to nitration is given, and the results of nitration over a range of solids are presented. Unusual dinitronaphthalene product ratios were achieved over Al-MCM-41. Reactions catalysed by heteropoly acid immobilised within the pores of mesopo

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5

Earle, Martyn John. "New approaches to aromatic substitution reactions with carbon electrophiles." Thesis, Loughborough University, 1992. https://dspace.lboro.ac.uk/2134/33242.

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The thesis gives an account of work directed towards developing new reagent systems and methodology, with particular reference to the Friedel–Crafts and Vilsmeier–Haack reactions of aromatic and heteroaromatlc compounds. Ways of improving regioselectivity and developing a stereoselective Friedel–Crafts reaction have been investigated for a range of hetero-atom stabilised carbocations. This work is divided into two main areas: (1) the synthesis and use of pyrophosphoryl chloride in the Vilsmeier–Haack reaction, the results of this has shed new light on the mechanism of this classical reaction;

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6

Jones, Craig Warren. "Nucleophilic aromatic substitution using supported copper(I) reagents." Thesis, University of York, 1989. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.236184.

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7

Nguyen, Quang. "Reinventing Aromatic Substitution: A Novel Look." TopSCHOLAR®, 2013. http://digitalcommons.wku.edu/theses/1292.

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Electrophilic aromatic substitution (EAS) and directed ortho-metalation (DoM) involve the direct substitution of an arene hydrogen. A major drawback involving EAS is the necessity for harsh forcing conditions for the reaction to proceed. Catalysts such as Lewis acids FeBr3 and AICI3 for the introduction of halogens and acyl groups, respectively, are each highly toxic and corrosive. Textbook preparations of aryl iodides classicaly involved the use of iodine and nitric acid. This approach affords only modest yields and does not provide regiospecific substitution of most substituted aromatics bec

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8

Duffy, Anne Merete. "Students' ways of understanding aromaticity and electrophilic aromatic substitution reactions." Connect to a 24 p. preview or request complete full text in PDF format. Access restricted to UC campuses, 2006. http://wwwlib.umi.com/cr/ucsd/fullcit?p3210647.

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Thesis (Ph. D.)--University of California, San Diego and San Diego State University, 2006.<br>Title from first page of PDF file (viewed June 7, 2006). Available via ProQuest Digital Dissertations. Vita. Includes bibliographical references (p. 280-290).

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9

Moonga, B. S. "The kinetics of protiodecarbonylation reactions." Thesis, Brunel University, 1986. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.375474.

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10

Donham, Leah L. "Gas-Phase Studies of Nucleophilic Substitution Reactions: Halogenating and Dehalogenating Aromatic Heterocycles." VCU Scholars Compass, 2018. https://scholarscompass.vcu.edu/etd/5645.

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Halogenated heterocycles are common in pharmaceutical and natural products and there is a need to develop a better understanding of processes used to synthesize them. Although the halogenation of simple aromatic molecules is well understood, the mechanisms behind the halogenation of aromatic heterocycles have been more problematic to elucidate because multiple pathways are possible. Recently, new, radical-based mechanisms have been proposed for heterocycle halogenation. In this study, we examine and test the viability of possible nucleophilic substitution, SN2@X, mechanisms in the halogenat

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11

Telu, Sanjay. "AN INVESTIGATION OF OXIDATITIVE-SUBSTITUTION REACTIONS OF POLYCYCLIC AROMATIC HYDROCARBONS AND OTHER ELECTRON-RICH AROMATIC COMPOUNDS WITH HYPERVALENT IODINE REAGENTS." University of Akron / OhioLINK, 2006. http://rave.ohiolink.edu/etdc/view?acc_num=akron1162492437.

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12

Schory, David Henry. "Quantum Chemical Investigations of Nucleophilic Aromatic Substitution Reactions and Acid Dissociations of Aliphatic Carboxylic Acids." Wright State University / OhioLINK, 2009. http://rave.ohiolink.edu/etdc/view?acc_num=wright1253480264.

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13

Liao, Jing-Piin. "A Reinvestigation of the Kinetics and Mechanism of Ligand Exchange in Mu-(2,2,8,8-Tetramethyl-3, 7-Dithianonane)-Decacarbonylditungsten(0)." Thesis, University of North Texas, 1988. https://digital.library.unt.edu/ark:/67531/metadc500831/.

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This student is interested in reinvestigating the kinetics and mechanism of the bridged compound in l,2-dichloroethane with triisopropyl phosphite and in finding the reasons why the values of competition ratio k₋₂ /k₃ in this reaction are so large.

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14

Liu, Jiangqiong. "Kinetic Studies of 6-Halopurine Nucleoside in SNAr Reactions; 6-(Azolyl, Alkylthio and Fluoro)-purine Nucleosides as Substrates for Suzuki Reactions." Diss., CLICK HERE for online access, 2007. http://contentdm.lib.byu.edu/ETD/image/etd1821.pdf.

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15

Chamberlin, Rachel Alexandra. "Some substitution reactions of aryl sulfides and aryl ethers with aliphatic amines in DMSO : the mechanism of base catalysis." Thesis, Durham University, 1995. http://etheses.dur.ac.uk/5213/.

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The reactions of several nitro-aromatic substrates with the aliphatic amines, n- butylamine, pyrrolidine and piperidine in DMSO have been studied. Reaction of the amines with trinitroaromatic compounds, such as ethyl thiopicrate, phenyl thiopicrate and phenyl 2,4,6-trinitrophenyl ether, was shown to occur in two well separated processes. A rapid reaction, occuring at an unsubstituted ring position, resulted in the formation of a a-adduct; this was followed by a slower substitution reaction, resulting in the displacement of the 1-substituent to give the amino-substituted compound. Kinetic resul

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16

Cook, Teresa L. "Developing Green One-Step Organic Reactions in the High Speed Ball Mill." University of Cincinnati / OhioLINK, 2014. http://rave.ohiolink.edu/etdc/view?acc_num=ucin1397736534.

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17

Norberg, Daniel. "Quantum Chemical Studies of Radical Cation Rearrangement, Radical Carbonylation, and Homolytic Substitution Reactions." Doctoral thesis, Uppsala : Acta Universitatis Upsaliensis, 2007. http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-8178.

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18

HADDAD-FAHED, OMAIMA. "Catalyse micellaire de reactions de substitution nucleophile aromatique comportant des reactifs electriquement charges." Paris 6, 1987. http://www.theses.fr/1987PA066419.

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19

Nonoyama, Nobuaki. "Mechanism and Selectivity in Nitration and Side-Reactions of Aromatic and Aliphatic Compounds with Nitrogen Oxides (NO2, NO3, N2O5, ONOO-)." 京都大学 (Kyoto University), 2000. http://hdl.handle.net/2433/181133.

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20

Zheng, Huaiben. "Kinetics and mechanism of the hydrolysis and nucleophilic attachment/substitution of transition metal carbene complexes : kinetics of carbon proton transfers that lead to aromatic anions /." Diss., Digital Dissertations Database. Restricted to UC campuses, 2006. http://uclibs.org/PID/11984.

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21

Xie, Sheng. "Perfluroaryl azides : Reactivities, Unique Reactions and their Applications in the Synthesis of Theranostic Agents." Doctoral thesis, KTH, Organisk kemi, 2015. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-172950.

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The work centersaround perfluoroaryl azides (PFAAs), and theirability to undergo certain fast and robusttransformations. The chemistry was furtherappliedfor biomedical applications. The first section focuses on the azide-aldehyde-amine cycloaddition using PFAAs. Experimental and computational investigations uncovered a fast azide-enamine cycloaddition to form triazolines, which spontaneously rearrange into stable amidine products. In addition, this transformation was explored in the formulation of pure nanodrugs. Because this reaction can introduce a phenyl and a perfluoroaryl moiety enabling

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22

Bielawski, Marcin. "Diaryliodonium Salts : Development of Synthetic Methodologies and α-Arylation of Enolates". Doctoral thesis, Stockholms universitet, Institutionen för organisk kemi, 2011. http://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-54738.

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This thesis describes novel reaction protocols for the synthesis of diaryliodonium salts and also provides an insight to the mechanism of α-arylation of carbonyl compounds with diaryliodonium salts. The first chapter gives a general introduction to the field of hypervalent iodine chemistry, mainly focusing on recent developments and applications of diaryliodonium salts. Chapter two describes the synthesis of electron-rich to electron-poor diaryliodonium triflates, in moderate to excellent yields from a range of arenes and iodoarenes. In chapter three, it is described that molecular iodine can

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23

Belaroussi, Rabia. "Synthèse et fonctionnalisation de nouveaux dérivés tricycliques [6-5-6] polyhétéroaromatiques à visée thérapeutique potentielle." Thesis, Orléans, 2016. http://www.theses.fr/2016ORLE2002/document.

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La découverte de nouveaux candidats susceptibles de lutter contre différentes pathologies, en l’occurrence le cancer et les maladies neurodégénératives, constitue l’un des principaux objectifs de notre groupe de recherche. Dans ce contexte, les travaux de cette thèse ont pour but principal, la conception de deux nouvelles classes d’hétérocycles de structure planes, jusqu’à ce jour, très rarement étudiées, à savoir les pyrido[2’,1’ :1,5]pyrazolo[3,4-d]pyridazines et les pyrido[2’,1’ :1,5]pyrazolo[3,4-d]pyrimidines. Ce manuscrit est essentiellement dédié à un travail de méthodologie décrivant le

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24

Ejjoummany, Abdelaziz. "Design et fonctionnalisation d’hétérocycles originaux de type bicycliques [5-5] et tricycliques [6-5-6] à visée thérapeutique potentielle." Thesis, Orléans, 2020. http://www.theses.fr/2020ORLE3141.

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L’accès à de nouveaux composés hétérocycliques originaux biologiquement actifs, constitue l’un des principaux objectifs de notre groupe de recherche. Dans ce contexte, les travaux de cette thèse ont pour but principal, la conception de trois nouvelles familles de composés hétérocycliques contenant un motif pyrazolique susceptibles de présenter des activités biologiques, à savoir les pyrido[1',2':1,5]pyrazolo[4,3-d]pyrimidine, les pyrrolo[3,4-c]pyrazoles et les pyrazolo[5,1-b]thiazoles. Ce manuscrit est essentiellement dédié à un travail de méthodologie décrivant les différentes voies d’accès à

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25

Lannuzel, Frédéric. "Influence des aromatiques sur la stabilité thermique des pétroles dans les gisements." Phd thesis, Institut National Polytechnique de Lorraine - INPL, 2007. http://tel.archives-ouvertes.fr/tel-00473215.

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Cette étude vise à mieux comprendre les réactions mpliquées dans le craquage thermique des huiles en basins sédimentaires. Des pyrolyses d'octane, de toluène et de mélanges octane/toluène ont été effectuées entre 330°C et 450°C et des pressions allant de 1 bar à 700 bar. Le mécanisme radicalaire développé permet de rendre compte de l'influence de la température et de la pression sur la distribution des produits ainsi que sur la conversion jusqu'aux conditions de gisement (200°C, 150-1000 bar). Les pyrolyses du toluène pur et du mélange octane/toluène ont permis de modéliser le rôle inhibiteur

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26

Yamuna, B. "Kinetics and mechanism of reactions of substrates with Aromatic Sulfonyl Chloramines and Bromamines." Thesis, 1987. http://hdl.handle.net/2009/2464.

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27

Li, Sheng Shan, and 盛珊琍. "The Research of Synthetical Mechanism and Chemical Reactions of Tricarbonyl Chromium Polycyclic Aromatic Compound." Thesis, 1994. http://ndltd.ncl.edu.tw/handle/70034276176963973203.

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碩士<br>靜宜大學<br>應用化學系<br>82<br>We have synthesized and exhibited a series of the sub- stituted, saturated-PAHCr(CO)▋.In the process of synthesis, because the PAHCr(CO)▋are difficult to be synthesized and low in yield,it is a great disadvantage in the application of organic synthesis. We have developed a modified synthetic way:the Cr(CO)▋L▋is used instead of Cr(CO)▋,and the solvent system and reaction temperature is changed.By the new synthetic way,we get a product of higher yield on the synth

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28

Lawton, Michelle Claire. "Aluminium triflate as a Lewis acid catalyst in some epoxide and aromatic transformations." Thesis, 2012. http://hdl.handle.net/10210/4536.

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M.Sc.<br>Lewis acids play an important role in catalysis; they are associated with mild conditions, high selectivities and unique reactivities. Traditional Lewis acids such as AlCb and BF3 successfully catalyse such well known reactions as the Friedel-Crafts acylation reaction, Aldol condensation reactions and many more. These catalysts, however, must be used in a stoichiometric amount and are destroyed during the aqueous workup procedures. Lately, there has been a lot of interest in the role of metal triflate as Lewis acid catalysts. They were found to be effective in a wide range of reaction

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29

Chuang, Chung-Lin, and 莊忠霖. "1,2,4-Triazines Chemistry: The Study on Reaction Mechanism of Rearrangement Cyclization, Oxidation, Bromination and Substitution Reactions." Thesis, 2007. http://ndltd.ncl.edu.tw/handle/52768817617861129359.

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碩士<br>高雄醫學大學<br>醫藥暨應用化學研究所碩士班<br>95<br>This study including synthesis and reaction mechanisms were divided into six parts. I. The base of mono and heterobicycles containing 1,2,4-triazine ring has synthesized. II. An intramolecular rearrangement- romatized ring cyclization mechanism for the compound 3-amino-2- benzyl-6-hydrazino-1,2,4-triazin-5(2H)-one(12) reacted with carbon disulfide in a water/pyridine mixture to afford bicyclic adduct 6-amino- 3-benzylmercaptor-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-one(18) is explored. III. 3-amino-1,2,4-triazin-5(2H)-one(2) and its 6-bromo derivative

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30

O'Connell, Jenny Lee. "Neighbouring group participation in electrophilic chlorination." Phd thesis, 1999. http://hdl.handle.net/1885/147694.

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