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Dissertations / Theses on the topic 'Ortho- metalation'

Author: Grafiati
Published: 4 June 2021
Last updated: 1 February 2022

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1

Timmons, Michael. "Directed Ortho-Metalation of Dimethylarylamines." TopSCHOLAR®, 2002. http://digitalcommons.wku.edu/theses/641.

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Site-specific product(s) from the reaction of benzene derivatives with various reagents is a need of researchers at numerous laboratories, particularly those in the pharmaceutical industry. Such derivatives can be synthesized directly, i.e., by substitution of a proton, using either of two procedures: electrophilic aromatic substitution (EAS) or directed ortho-metalation (DoM). Directed ortho-metalation (DoM) is an alternative aromatic substitution process initiated by organolithium reagents which provides regiospecific substitution exclusively at the ortho- position (equation). The focus of t
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2

Woosley, Barry. "Directed ortho Metalation in Hydrocarbon Solvents: Opposing Pi-Resonance Effects." TopSCHOLAR®, 2004. http://digitalcommons.wku.edu/theses/539.

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Hydrocarbon solvents are known to be unreactive toward organolithium reagents and do not typically support ortho-metalation reactions without the aid of a promoter. An exception would be an arene substrate having the capability to bidentate complex to the reactive alkyllithium dimer, which enables ortho-metalation to occur in high yields. A second, more limiting exception, would be that the arene substrate possesses localized lone pairs of electrons, as is the case when the directed ortho metalating group (DMG) is located in the benzyl position. The work reported here centers upon developing a
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3

Friesen, Carl. "Directed Ortho-Metalation of the Three Methyl Anisoles in Various Media." TopSCHOLAR®, 1996. http://digitalcommons.wku.edu/theses/870.

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Directed ortho-metalation (DoM) is a very useful alternative to electrophillic aromatic substitution (EAS) for the synthesis of substituted aromatic compounds. DoM is highly regiospecific providing metalation chiefly in the ortho-position. However, lateral (a-) metalation of an alkyl side-chain and ortho-metalation of a second ortho-position can compete. Investigation of the three methylanisoles was therefore undertaken to determine the interplay between these factors and to discover metalation conditions to achieve selectivity. This goal was uniquely achieved for p-methylanisole where conditi
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4

Macklin, Todd Kristopher. "The development of sulfamates as latent directed metalation groups. Total synthesis of schumanniophytine. Divergent synthesis of substituted chromone 3- and 8-carboxamides." Thesis, Kingston, Ont. : [s.n.], 2007. http://hdl.handle.net/1974/925.

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5

Milburn, Claire Louise Maud Jackson. "The directed ortho metalation reaction of aryl O-carbamates on solid support." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2001. http://www.collectionscanada.ca/obj/s4/f2/dsk3/ftp05/MQ63340.pdf.

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6

Cai, Xiongwei. "Regiospecific synthesis of alkylphenanthrenes using a combined directed ortho metalation, DoM, (Suzuki-Miyaura cross coupling), directed remote metalation, DreM, methodology." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2001. http://www.collectionscanada.ca/obj/s4/f2/dsk3/ftp05/MQ63276.pdf.

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7

Kendall, Christopher Nicholas Owen. "The directed ortho metalation - Suzuki-Miyaura cross-coupling connection, towards the total synthesis of dehydrorabelomycin." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2000. http://www.collectionscanada.ca/obj/s4/f2/dsk1/tape3/PQDD_0020/MQ54462.pdf.

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8

Lai, Ping-Shan. "Directed ortho metalation-boronation Suzuki-Miyaura cross coupling leading to synthesis of azafluorenol core liquid crystals." Thesis, Kingston, Ont. : [s.n.], 2007. http://hdl.handle.net/1974/511.

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9

Michaux, Jérôme. "Méthodologies d'accès à des N-hydroxyphtalimides hautement substitués, vers de nouveaux catalyseurs d'oxydation aérobie." Thesis, Grenoble, 2012. http://www.theses.fr/2012GRENV071/document.

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Dans un contexte industriel où les réactions d'oxydation sont réalisées dans des conditions qui ne satisfont pas toujours les principes de la chimie verte, notre groupe étudie des catalyseurs de structure N-hydroxyphtalimide (NHPI), pour l'oxydation aérobie de substrats organiques variés dans des conditions douces. Dans le but d'obtenir des catalyseurs plus actifs, deux familles d'analogues hautement substitués sur le noyau phtalimide ont été préparées, suivant deux nouvelles méthodologies de synthèse. La première consiste en la bis-ortho-métallation / silylation d'acides ortho-phtaliques non
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10

Chauder, Brian Andrew. "Combined directed ortho metalation-transition metal catalyzed coupling reactions for the synthesis of chromenes, ergot alkaloids, and biaryl macrocycles." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2001. http://www.collectionscanada.ca/obj/s4/f2/dsk3/ftp04/NQ63410.pdf.

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11

Onuska, Nicholas Paul Ralph. "Studies Towards the Synthesis of 2,5-Disubstituted-3-Fluorothiophenes Using a Directed Ortho-Metalation/Nickel-Catalyzed Cross-Coupling Approach." Kent State University Honors College / OhioLINK, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1460652408.

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12

Green, Anthony Laine. "The Directed ortho Metalation of pyridine derivatives with in situ boronation and links to the Suzuki-Miyaura cross coupling reaction." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2001. http://www.collectionscanada.ca/obj/s4/f2/dsk3/ftp04/MQ63310.pdf.

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13

Yin, Chunfeng. "Regiospecific synthesis of chlorodihydroxybiphenyls and synthesis of 3,3'-bisaryl substituted BINOLs by combined directed ortho metalation (DoM) and Suzuki-Miyaura cross coupling." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2001. http://www.collectionscanada.ca/obj/s4/f2/dsk3/ftp05/MQ63395.pdf.

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14

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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15

Peel, Andrew James. "Group 11 'ate bases : towards an understanding of solid- and solution-state structures." Thesis, University of Cambridge, 2017. https://www.repository.cam.ac.uk/handle/1810/267910.

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Lithium bis(amido)cuprates are an important class of bimetallic base, which can chemo- and regioselectively metalate aromatic compounds, via directed ortho cupration (DoCu). This thesis begins with an introduction to aspects of the chemistry of organolithium compounds, group 11 organometallic compounds and their lithium 'ate complexes. Examples of such synergic bases are presented and the introduction is concluded with a discussion of lithium bis(amido)cuprate bases, which along with their silver congeners, are the subject of this dissertation. In general, syntheses involve the addition of a l
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16

Andersson, Hans. "Reaction between grignard reagents and heterocyclic N-oxides synthesis of substituted pyridines, piperidines and piperazines /." Doctoral thesis, Umeå : Department of Chemistry, Umeå University, 2009. http://urn.kb.se/resolve?urn=urn:nbn:se:umu:diva-25619.

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17

Aissaoui, Regadia. "Réaction de substitution nucléophile aromatique des acides naphtoïques ortho-fluorés/méthoxylés avec les réactifs de Grignards et les organolithiens (SNArAB)." Phd thesis, Université du Maine, 2012. http://tel.archives-ouvertes.fr/tel-00684960.

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Dans ce travail, il est montré que les alkyl/vinyl/aryl lithiens et magnésiens réagissentavec les acides C-1(F/OMe) naphtoïques en l'absence de catalyseur métallique. Cette nouvelleréaction de substitution nucléophile aromatique permet potentiellement de préparer n'importequel biaryle tout en s'affranchissant des étapes de protection et de déprotection de la fonctionacide (CO2H). Les alkyllithiens linéaires et ramifiés réagissent avec la même efficacité que lesalkylmagnésiens même à basse température (-78 °C). Le déplacement d'un fluor ou d'unméthoxy s'effectue avec la même facilité. L'absence
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18

Alessi, MANLIO. "Synthetic Methods and Application Based on Directed ortho Metalation and Suzuki Cross Coupling Strategies." Thesis, 2008. http://hdl.handle.net/1974/1634.

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The Directed ortho Metalation reaction is described in Chapter 1 of this thesis with particular emphasis on its mechanism and synthetic potential. Chapter 2 contains a review of the DoM (Directed ortho Metalation) of pyridine systems and describes the conditions that allow the one-pot DoM (Directed ortho-Metalation)-Boronation-Suzuki-Miyaura cross coupling of pyridines 2.263a-c, 2.351-2.53 (Table 2.9) bearing several DMGs (Directed Metalation Groups) including the synthetically versatile diethyl amide functionality without incurring into commonly observed self-condensation processes. The met
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19

Blackburn, Thomas. "I. PROGRESS IN DIRECTED ortho METALATION II.II. GENERATING CHIRALITY IN PERIODIC MESOPOROUS ORGANOSILICA." Thesis, 2009. http://hdl.handle.net/1974/5238.

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Chapter 1 constitutes a review of current methods of aromatic substitution focusing on Directed ortho Metalation (DoM) and Directed remote Metalation (DreM). The field of mesoporous silica is reviewed in Chapter 2, focusing on the preparation, characterization, and application of mesoporous silicates. Chapter 3 presents an introduction of phosphorus based Directed Metalation Groups (DMGs). The development of the directed ortho metalation (DoM) reaction of the tetraethyl phosphorodiamidate DMG is described. In addition to being one of the most powerful DMGs, migration of the OPO(NEt2)2 group to
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20

MORRISON, MATTHEW. "A Convenient Synthesis of Pyrrolnitrin and Related Halogenated Phenylpyrroles." Thesis, 2009. http://hdl.handle.net/1974/5265.

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This thesis details a straightforward synthetic route to the antifungal compound pyrrolnitrin 1.2, along with several analogous halogenated phenylpyrroles. The proposed synthetic protocol involved the Suzuki-Miyaura cross-coupling of appropriately halogenated pyrrole pinacolboronate esters and aryl compounds. In the efforts towards preparing the cross-coupling partners, we report a regiospecific and high yielding synthesis of a 3-chloro pyrrole compound 2.14, its brominated analog 2.16, an iodinated analog 2.17, and the corresponding pinacolboronate ester 2.18. We also report a generalized re
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