synthesis and reactions of fluorinated aromatics by Alison Marion Callan

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Published by University of Birmingham in Birmingham .

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Thesis (Ph.D) - University of Birmingham, School of Chemistry, Faculty of Science.

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Statementby Alison Marion Callan.
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Open LibraryOL17163801M

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Modern Synthesis Processes and Reactivity of Fluorinated Compounds focuses on the exceptional character of fluorine and fluorinated compounds.

This comprehensive work explores examples taken from all classes of fluorine chemistry and illustrates the extreme reactivity of fluorinating media and the peculiar synthesis routes to fluorinated materials.

A novel aromatic fluorinated monomer with pendant alkyl-sulfonate group was synthesized and polymerized under aqueous ATRP conditions. The monomer was prepared in two reaction steps from 2,3,4,5,6-pentafluorostyrene through a nucleophilic substitution of the labile para -fluorine atom by hydroxyl group followed by sulfopropylation with 1, by: 4.

We propose a simple, efficient and green reaction protocol for the preparation of fluorinated organic compounds by sequential halogen exchange of aromatic in the presence of ionic liquids.

The synthesis and characterization of a series of fluorinated polyimides from a novel diphthalic dianhydride, 4,4’-(2,2,2-trifluoropentafluorophenylethylidene)diphthalic anhydride (8 FDA) and several aromatic diamines and the synthesis of bis(3,4-dimethylphenyl)pentafluorophenyltrifluoromethylmethane (8 FTM) and 2-(3,4-dimethylphenyl)pentafluorophenyltrifluoromethylethanol Cited by: 1.

Functionalization of Fluorinated Aromatics by Nickel‐Mediated C H and C F Bond Oxidative Addition: Prospects for the Synthesis of Fluorine‐Containing Pharmaceuticals Samuel A.

Johnson Department of Chemistry and Biochemistry, University of Windsor, Windsor, ON, Canada, N9B 3P4Cited by:   Functionalization of Fluorinated Aromatics by Nickel‐Mediated C H and C F Bond Oxidative Addition: Prospects for the Synthesis of Fluorine‐Containing Pharmaceuticals Samuel Synthesis and reactions of fluorinated aromatics book.

Johnson Department of Chemistry and Biochemistry, University of Windsor, Windsor, ON, Canada, N9B 3P4. Numerous fluorinated (hetero)aromatic compounds have been synthesized by using synthesis and reactions of fluorinated aromatics book Diels–Alder reaction of fluorinated dienes/dienophiles with subsequent aromatization of the initially formed [4+2]‐cycloaddition products by various by: 4.

The synthesis of 5-fluoro- and 7-methyl-indole and -tryptophane. Journal of Heterocyclic Chemistry2 (3), DOI: /jhet   The Mallory reaction of 1,2-diarylhexafluorocyclopentene (1, aryl = 3-bromophenyl; 2, aryl = 4-bromophenyl) under light irradiation (λ = nm) in the presence of iodide proceeded to give dibromophenanthrene derivatives, 3 and 4.

With contributions from experts from both industry and academia, the book covers the chemistry, synthesis, and applications of fluorinated heterocycles with chapters on: Three- four- five- six.

In general, synthesis of –CF 3-activated bishalo monomers (Scheme ) was carried out by Pd-catalyzed Suzuki-coupling, which involves the synthesis of boronic acids from 2-fluoro- or 2-chlorobromobenzotrifluoride by the Grignard reaction in the first step, followed by reaction with trimethyl borate and successive hydrolysis, and finally by cross-coupling with the dibromo compounds.

This article covers the preparation, properties, reactions, and applications of three types of fluorinated aromatic compounds: ring-fluorinated aromatics, side-chain fluorinated aromatics and.

Fluorinated aromatic polyester synthesis Highly fluorinated aromatic polyesters were prepared by melt polycondensation of TFPA with EG. A typical synthesis procedure is described as follows: a direct polycondensation reaction was carried out in a ml round-bottomed glass reactor with a stirring assembly, a thermometer, a nitrogen gas inlet tube and a distillation by: This simple metal-free protocol enables the chemoselective introduction of a fluorine atom into various aromatic and aliphatic compounds and serves as a powerful tool for the efficient synthesis of fluorinated molecules.

Amaoka, M. Nagamoto, M. Inoue, Org. Lett.,15, Synthesis and Chemical Transformation of Six‐Membered Aromatic Heterocycles Containing Perfluoroalkyl Groups Viacheslav A.

Petrov DuPont Central Research and Development, Experimental Station, P.O. BoxWilmington, DE ‐, USA. The book begins with a discussion of fluorine's unique combination of properties, including size, electronic effects, and hydrophobicity, as well as the historical development of its product applications.

It explains methods for introducing fluorine into an aromatic ring, focusing on nucleophilic fluorine transfer reactions. Synthesis of Novel Fluorinated 4-Aminoquinoline Derivatives Article in Tetrahedron Letters November with 54 Reads How we measure 'reads'. Modern Carbon–Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis.

Chemical Reviews(2), DOI: /crb. Samuel D. Al-Masum, M., Islam, T. and Clopton, G. () Efficient Cross-Coupling Reaction of Aryltrifluoroborates and Aroyl Chlorides for the Synthesis of Fluorine Substituted Aromatic Ketones.

International Journal of Organic Chemistry, 9, doi: /ijoc Synthesis and nucleophilic aromatic substitution of 3-fluoronitro(pentafluorosulfanyl)benzene Article (PDF Available) in Beilstein Journal of Organic Chemistry 12(1) February For the synthesis of complex fluorinated products, the presented sequences are more convenient and effective then direct fluorination or polyfluoroalkylation.

Abstract Numerous fluorinated (hetero)aromatic compounds have been synthesized by using the Diels–Alder reaction of fluorinated dienes/dienophiles with subsequent aromatization of the. Synthesis and characterization of novel fluorinated aromatic polyimides derived from 1,1‐bis(4‐amino‐3,5‐dimethylphenyl)‐1‐(3,5‐ditrifluoromethylphenyl)‐2,2,2‐trifluoroethane and various aromatic dianhydrides.

Nucleophilic aromatic substitution of fluorine leading to compounds 3 was investigated ().With low-boiling alcohols (MeOH, EtOH), the reactions were heated under reflux using the alcohol as a solvent and excess of potassium hydroxide (Table 1, entries 1 and 2).For alcohols with higher boiling points, the reactions were performed with sodium hydride (Table 1, entries 3 and 4).

Noveski D, Braun T, Neumann B, Stammler A, Stammler H-G () C–F or C–H bond activation and C–C coupling reactions of fluorinated pyridines at rhodium: synthesis, structure and reactivity of a variety of tetrafluoropyridyl complexes.

Dalton Trans doi: /BK. The book provides advanced and updated information on the latest synthesis routes to fluorocompounds and the involved reaction mechanisms. Special attention is given to the unique reactivity of fluorine and fluorinated media, along with the correlation of those properties to valuable applications of fluorinated cturer: Elsevier.

Synthesis and structure of rhodium(i) silyl carbonyl complexes: photochemical C–F and C–H bond activation of fluorinated aromatic compounds.

Dalton Transactions44 (20), DOI: /C5DTK. Raza, T. Braun. Synthesis, reactions, and application of furans and benzofurans bearing a fluorine atom and a trifluoromethyl group are reviewed. Synthesis, reactions, and application of furans and benzofurans bearing a fluorine atom and a trifluoromethyl group are reviewed.

Large-scale preparation of aromatic fluorides via electrophilic fluorination with. Emerging Fluorinated Motifs: Synthesis, Properties and Applications begins with a description of carbon-linked fluorine-containing groups that include monofluoromethyl and difluoromethyl groups.

It then details combinations of heteroatoms, Oxygen, Sulfur, Selenium, Nitrogen, and Phosphorus with fluorine-containing groups, outlining subsections of the most popular current motifs. Fluoropolymers display a wide range of remarkable properties and are used in a number of applications including high performance elastomers, thermoplastics, coatings for optical fibers, and hydrophobic and lipophobic surfaces.

The set contains two books, Fluorinated Polymers: Synthesis, Properties, Processing and Simulation and Fluorinated Polymers: Applications. Introduction. Direct fluorination of complex organic molecules is a useful, although quite rare, method for synthesis of F labeled PET compounds [].Recently we reported a new reaction of this type, a direct fluorination of phenolsulfonphthalein (Phenol Red) [].The fluorine-containing products of the reaction act as pH indicators with potential application for direct in vivo measurement of Cited by: 7.

This review reports a survey of our recent results on the synthesis of arylenevinylene polymers and oligomers selectively functionalized with fluorine atoms on aromatic and/or vinylene units. The synthetic methods developed are based on Pd-catalyzed organometallic cross-coupling reactions and in particular on the Stille coupling between vinyl.

Petrov VA () Synthesis and chemical transformation of Six-membered aromatic heterocycles containing perfluoroalkyl groups. In: Petrov VA (ed) Fluorinated heterocyclic compounds: synthesis, chemistry, and applications. Part I. Wiley, Hoboken, pp – Google Scholar. RESULTS AND DISCUSSION.

As shown in Scheme 1, we postulated that repeated S N Ar reactions of the novel benzophenone 10 might allow access to other fluorinated benzophenones (11–12), as well as xanthones, acridones, and thioxanthones (13), as precursors to more highly conjugated fluorophores (14).

45 The high selectivity observed for the sequential addition of multiple. Halogenation Nitration Sulfonation Friedel-Crafts alkylation Friedel-Crafts acylation Birch reduction. Iron(III) fluorinated porphyrins play a central role in the biomimetics of heme enzymes and enable cleaner routes to the oxidation of organic compounds.

The present work reports significant improvements in the eco-compatibility of the synthesis of 5,10,15,tetrakis-pentafluorophenylporphyrin (H2TPFPP) and the corresponding iron complex [Fe(TPFPP)Cl], and the use of [Fe(TPFPP)Cl] as an. Treatment of various fluorinated internal alkynes with 10 mol% of RhCl 3 H 2 O and 30 mol% of i-Pr 2 NEt in toluene at the reflux temperature for 18 h gave the corresponding trimerization products as an isomeric mixture in high yields.

Cycloaddition using equiv. of fluorinated alkynes and equiv. of non-fluorinated alkynes under the same reaction conditions as in the trimerization led. Fluorinated polyurethanes with a glass transition temperature as low as − °C and a decomposition onset temperature of – °C were prepared by a reaction of fluorinated alcohols with aromatic and cycloaliphatic diisocyanates in solution or melt.

Fluorinated polyimides were prepared from the twisted benzidine monomer containing two trifluoromethyl (CF3) groups on one aromatic ring. The diamine monomer having a rigid and nonplanar structure was polymerized with typical dianhydride monomers including BPDA, BTDA, ODPA, 6-FDA, and PMDA, to obtain the corresponding polyimides.

Most polyimides are soluble in organic solvents due to. Nucleophilic aromatic substitution of fluorine leading to compounds 3 was investigated (Table 1).With low-boiling alcohols (MeOH, EtOH), the reactions were heated under reflux using the alcohol as a solvent and excess of potassium hydroxide (Table 1, entries 1 and 2).For alcohols with higher boiling points, the reactions were performed with sodium hydride (Table 1, entries 3 and 4).

Intramolecular photocyclization of stilbene derivatives (Mallory reaction) is one of the efficient methods for building polycyclic aromatic hydrocarbon (PAH) frameworks, and is also expected to be applicable to synthesis of fluorine-containing PAHs (F-PAHs).

In this study, dibenzoanthracene-type (4a) and benzoperylene-type (4b) F-PAHs were synthesized using the Mallory reaction of the 1,4. International Journal of Organic Chemistry Vol No(), Article ID,6 pages /ijoc Efficient Cross-Coupling Reaction of Aryltrifluoroborates and Aroyl Chlorides for the Synthesis of Fluorine Substituted Aromatic Ketones.Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, 2nd, Completely Revised and Enlarged Edition.

a well-produced book with attractive graphics, photos and schemes. Throughout the book, coloured electrostatic maps of small SELECTED FLUORINATED STRUCTURES AND REACTION TYPES Difluoromethylation and Halodifluoromethylation.This review is an overview of our previous work on the synthesis and properties of poly(p-phenylenevinylene)s (PPVs) selectively fluorinated in different positions of the conjugated backbone.

Both the synthetic challenges and the effects of functionalization with fluorine atoms on the optical behavior are discussed, highlighting the peculiarities and the interest of this class of conjugated.

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