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Full-Text Articles in Organic Chemistry

Organocatalyzed Synthesis Of Epoxides From Chalcones Utilizing Amino Acids, Sabrina N. Kegeler Apr 2018

Organocatalyzed Synthesis Of Epoxides From Chalcones Utilizing Amino Acids, Sabrina N. Kegeler

Master's Theses

The epoxide functional group is important throughout the chemical and pharmaceutical industries, as well as in nature. In the chemical industry, epoxides are present in resins and fragrances. In the pharmaceutical industry, epoxide-containing compounds are used as intermediates in the manufacturing of drugs. In nature, many natural products contain epoxide groups and are used for medicinal purposes, and for models to create synthetic molecules.

One approach to epoxide synthesis involves the use of an alkene precursor, a base, and an oxidizing agent. This is where my investigations began. The first step was to optimize the epoxidation reaction, examining substrate scope ...


Mechanistic Investigations Of The Iron(Iii)-Catalyzed Carbonyl-Olefin Metathesis Reaction, Susan Phan Jan 2018

Mechanistic Investigations Of The Iron(Iii)-Catalyzed Carbonyl-Olefin Metathesis Reaction, Susan Phan

Master's Theses

Iron(III)-catalyzed carbonyl-olefin ring-closing metathesis represents a new approach toward the assembly of molecules traditionally generated by olefinˆ’olefin metathesis or olefination. Herein, we report detailed synthetic, spectroscopic, kinetic, and computational studies to determine the mechanistic features imparted by iron(III), substrate, and temperature to the catalytic cycle. These data are consistent with an iron(III)-mediated asynchronous, concerted [2+2]-cycloaddition to form an intermediate oxetane as the turnover-limiting step. Fragmentation of the oxetane via Lewis acid-activation results in the formation of five- and six-membered unsaturated carbocycles.


Development Of An Improved Synthesis Of S-D-Ribosyl-L-Homocysteine (Srh) And Progress Toward Srh Analogs Modified At The C3 Position, Emily Rouse Dec 2017

Development Of An Improved Synthesis Of S-D-Ribosyl-L-Homocysteine (Srh) And Progress Toward Srh Analogs Modified At The C3 Position, Emily Rouse

Master's Theses

Quorum sensing is a system that facilitates bacteria turning on and off gene expression depending on population density. System 2 quorum sensing is utilized by both Gram positive and Gram negative bacteria, and the quorum sensing molecule used in this system is AI-2. AI-2 is biosynthesized by the enzyme LuxS from the precursor SRH. This thesis describes an improved synthesis of SRH through the exploration of different protecting group strategies. The knowledge gained from the improved synthesis of SRH is then applied toward the synthesis of SRH analogues with increased steric bulk installed through use of a stereoselective anti-Mannich reaction ...


C(Sp2)–H Functionalizations Employing 2-Aminophenyl-1h-Pyrazole As A New Removable Directing Group, Wan-Chen Lee May 2017

C(Sp2)–H Functionalizations Employing 2-Aminophenyl-1h-Pyrazole As A New Removable Directing Group, Wan-Chen Lee

Master's Theses

2-Aminophenyl-1H-pyrazole (2-APP) was discovered as a novel removable bidentate directing group for copper-mediated aerobic oxidative C(sp2)–H bond amidation and sulfonamidation bearing a wide range of sulfonamides, When Cu(OAc)2 was employed as the copper source, 1,1,3,3-tetramethylguanidine (TMG) as an organic base, the reaction, optimally carried out overnight in DMSO at 80 °C in open air, produced a variety of products in moderate to excellent yields. In addition, C(sp2)–H bond chlorination has been developed by using this auxiliary, employing trichloroacetamide as a new chlorine source. Furthermore, this unprecedented directing group also can assist ...


Correlation Of Polymer Performance And Hansen Solubility Parameters, Daniel Jobse Mania Aug 2016

Correlation Of Polymer Performance And Hansen Solubility Parameters, Daniel Jobse Mania

Master's Theses

Ready-to-use (RTU) grout is becoming more important to the finish and remodeling construction industry. Market research shows it is a fast-growing product that not only is creating its own space, but is beginning to supplant existing technology.

The original intent of this research was to investigate formulation parameters and how they affect grout performance. It was learned that particle size and oil absorption (OA) value are important filler properties that affect performance as much as adequate packing density and optimal pigment volume concentration (PVC) without going beyond critical PVC (CPVC).

Polymer architecture was also determined to be extremely important, but ...


Application Of Electrospray Ionization Mass Spectrometry For Ionic Liquids And Their Biodegradation Products, Sepideh Rahbarirad Apr 2016

Application Of Electrospray Ionization Mass Spectrometry For Ionic Liquids And Their Biodegradation Products, Sepideh Rahbarirad

Master's Theses

Ionic liquids (ILs) are organic salts with unique physico-chemical properties and are used as green alternatives to volatile organic solvents. ESI-MS is a sensitive technique to detect these stable, permanent ions. My research focused on (1) Identification of biodegradation products of ionic liquids and (2) Multiplexed tandem MS by modulation of ionization efficiency.

Studies, have demonstrated that ILs are toxic to the environment, which makes their biodegradability an important consideration. In this work, metabolites generated during the biodegradation of 1-butyl-3-methylimidazolium chloride (BMIM), a degradation resistant and commonly used ionic liquid, are identified using high performance liquid chromatography-mass spectrometry (LC-MS).

Multiplexed ...


Investigations Of Thioether Generation For S-D-Ribosyl-L-Homocysteine Synthesis, Brendan Corcoran May 2015

Investigations Of Thioether Generation For S-D-Ribosyl-L-Homocysteine Synthesis, Brendan Corcoran

Master's Theses

Creation of the thioether linkage is a fundamental step for the chemical preparation of the bacterial quorum sensing molecule S-D-ribosyl-L-homocysteine (SRH). Although previous preparations of SRH and its analogues have been reported in the literature, they employ assorted methods with varied results. Therefore, a reassessment of the methodology used for synthetic preparation of the thioether bond in SRH-like molecules is here considered. This work examines four methods of thioether generation following two mechanisms, bimolecular nucleophilic substitution (SN2) and radical-initiated thiol-ene coupling, in an attempt to generate SRH in a more efficient and reproducible manner. Both mechanisms address ...


Preparation Of Organofluorine Compounds: Exploring Mono-, Di-, And Tri-Fluorination, Diandra M. Rudzinski Jan 2013

Preparation Of Organofluorine Compounds: Exploring Mono-, Di-, And Tri-Fluorination, Diandra M. Rudzinski

Master's Theses

Organofluorine compounds exhibit biological activity and have advantageous properties for drug design. Natural occurring fluorinated molecules are rare, demanding new synthetic methods for their preparation. A novel route to access trifluoromethyl ketones from Weinreb amide precursors is discussed. This is the first documented method for the use of the Ruppert-Prakash reagent, (trifluoromethyl)trimethylsilane, for the production of trifluoromethyl ketones from amide starting materials. This method is tolerant of aryl and alkyl substrates exhibited by their moderate to excellent yields. A discussion of the unusual reactivity of these amides, their selectivity for mono-trifluoromethylation, and other mono-, and di-fluorination attempts are reported.


Preparation Of Nitrogen-Containing Heterocycles Via Cyclization Of Pyridine-Tethered Organolithiums, Elizabeth Archer Nov 2012

Preparation Of Nitrogen-Containing Heterocycles Via Cyclization Of Pyridine-Tethered Organolithiums, Elizabeth Archer

Master's Theses

No abstract provided.


Synthesis Of Half-Loaded Nitroimidazole Indocyanine Green Dyes Attached To Carbon Nanotubes, Courtney L. Stanford Jul 2012

Synthesis Of Half-Loaded Nitroimidazole Indocyanine Green Dyes Attached To Carbon Nanotubes, Courtney L. Stanford

Master's Theses

Indocyanine green dye is the only FDA approved NIR fluorescent dye that can be used in humans. 2-Nitroimidazoles are very effective radiosensitizers, have low cytotoxicity, and target hypoxic tissue. By coupling the two together, hypoxic tumors can be targeted and imaged. Previous work has been done to couple 2-nitroimidazole to both sides of the indocyanine green dye. This work focuses on expanding that concept to couple 2-nitroimidazole to only one side of the dye, thus allowing for the other end to be available to couple to another compound, generating a half loaded 2-nitroimidazole indocyanine green dye. In theory, this half-loaded ...


Fluorescence Tagging Of Marine Low Molecular Weight Carboxylic Acids, Brian C. Gismervik Jul 2012

Fluorescence Tagging Of Marine Low Molecular Weight Carboxylic Acids, Brian C. Gismervik

Master's Theses

This thesis aims at the evaluation of the best amide bonding strategy that places a fluorescence aminomethyl coumarin tag onto a LMW organic acid in aqueous solution. A three-stage study was conducted. First, a suitable aminomethyl coumarin fluorophore was synthesized. Second, a library of acid-derivatized standards was synthesized for use in optimizing the anticipated HPLC separation of a mixture of LMW acids expected to be found in marine samples. Third, the aforementioned amide coupling strategies were screened to identify the most applicable method for our reaction conditions to the tagging of LMW organic acids in a large number of field ...


Synthesis Of S-Ribosyl-L-Homocysteine And Analogs Modified At The Homocysteine-C3 Position, Ruoyi Liu May 2012

Synthesis Of S-Ribosyl-L-Homocysteine And Analogs Modified At The Homocysteine-C3 Position, Ruoyi Liu

Master's Theses

Quorum sensing (QS) is a process of bacterial cell-to-cell communication that conveys population density information in order to coordinate gene expression to produce synchronized behaviors. QS regulates the expression of virulence genes in many species of bacteria; hence, the manipulation of QS pathways may lead to treatment options against many bacterial diseases. The LuxS enzyme converts S-ribosyl-L-homocysteine (SRH) into homocysteine (HCys) and 4(S),5-dihydroxypentane-2,3-dione (DPD), which is the precursor of autoinducer-2 (AI-2). Thus, inhibitors of LuxS could prevent QS by halting the conversion of SRH to AI-2 rendering the cell “uncommunicative”. This work shows the successful chemical ...


The Synthesis Of A Homologous Series Of Alkyl Lumazines And Their Application To The Dispersion Of Carbon Nanotubes, William P. Kopcha Apr 2012

The Synthesis Of A Homologous Series Of Alkyl Lumazines And Their Application To The Dispersion Of Carbon Nanotubes, William P. Kopcha

Master's Theses

In this thesis, the synthesis of a series of alkyl lumazine surfactants (LCn) is reported. Their application to the dispersion of both CoMoCAT and HiPco single-walled carbon nanotubes (SWNTs) is examined in detail and the thermal stability and chirality selection properties of dispersions made with these surfactants were compared both between themselves and with an alkyl flavin surfactant (FC12). Lumazine alkyl chain length exhibited some control over the quality and the quantity of SWNTs dispersed. LC10 was deemed most appropriate for comparison with FC12 based on considerations of solubility and nanotube individualization. Although the lumazines were ...


Improved Synthesis Of The Longtailed Mealybug Pheromone, Johanna M. Bakonyi Apr 2012

Improved Synthesis Of The Longtailed Mealybug Pheromone, Johanna M. Bakonyi

Master's Theses

No abstract provided.


Towards The Synthesis Of Alpha-Aminogalactosylceramides, Shaun C. Christian May 2011

Towards The Synthesis Of Alpha-Aminogalactosylceramides, Shaun C. Christian

Master's Theses

No abstract provided.


Investigation Of Electron Transfer From Carbonylmetallate Anions To Electron Acceptors, Joseph Kofi Agyin Jun 1993

Investigation Of Electron Transfer From Carbonylmetallate Anions To Electron Acceptors, Joseph Kofi Agyin

Master's Theses

This study investigated electron transfer potential of the carbonyl-metallate anions cyclopentadienylirondicarbonyl and methylcyclopentadienyliron-dicarbonyl anions to the electron acceptors 2,2-dinitropropane, 1,1-dinitrocyclohexane, $\alpha$,p-dinitrocumene, methyl cyclopentadienyl-mercury(II) chloride and iodide.

The findings from this study indicated that: (a) the expected products could not be obtained from reactions of the anions with the dinitro-substrates, and (b) the mercurials reacted with the anions but the expected products, (ferrocene and methylferrocene), was the minor product and an unexpected (methyl) cyclopentadienylirondicarbonylmercury(II)-chloride or iodide was the major product.


Synthesis Of Symmetric And "Mixed-Ligand" Homocyclopentadienyl Ruthenocenes, John Adjeiku Amanfu Dec 1992

Synthesis Of Symmetric And "Mixed-Ligand" Homocyclopentadienyl Ruthenocenes, John Adjeiku Amanfu

Master's Theses

No abstract provided.


Synthesis Of Organometallic Polymers, Po-Chang Chiang Jun 1992

Synthesis Of Organometallic Polymers, Po-Chang Chiang

Master's Theses

By the middle of the nineteenth century, organic chemists found high molecular weight compounds as by-products of some of their experiments. These compounds were thought of as products of a failed reaction. It was not until sixty years ago that the first polymers were deliberately synthesized. Today polymers are used in almost every facet of life and they are becoming more important with each passing day.

This research project focused on synthesizing conducting organometallic polymers. By linking aromatic rings with transition metals, the resultant polymers should have good electrical conductivity because of the interaction of (a) the p electrons on ...


The Synthesis Of Chiral Building Blocks Using Beta-Hydroxy Sulfoxide Dianions, Carla M. Edwards Jan 1992

The Synthesis Of Chiral Building Blocks Using Beta-Hydroxy Sulfoxide Dianions, Carla M. Edwards

Master's Theses

No abstract provided.


Reductive Cleavage Of Cyclopentadienylmanganese Tricarbonyl, Mani S. Iyer Dec 1991

Reductive Cleavage Of Cyclopentadienylmanganese Tricarbonyl, Mani S. Iyer

Master's Theses

Since the isolation of ferrocene in 1951, it has been shown to behave like benzene and may be acylated, sulfonated, metalated, and arylated. Like benzene, it also resists hydrogenation.

Daniel Trifan and Louis Nicholas (1957) were the first to show that ferrocene can be smoothly degraded by lithium and ethylamine. The isolation of free cyclopentadienyl ion on hydrolysis of the reaction mixture indicates that the cleavage leads initially to cyclopentadienyl lithium salt. A similar procedure applied to cyclopentadienylmanganese tricarbonyl also resulted in the formation of cyclopentadienyl lithium salt. This, when added to ferrous chloride, gave ferrocene. This technique can be ...


Micellar Catalysis Of Hydrolysis Of Substituted Hydroxamic Acids With Perfluorooctanoic Acid, Zhongyuan He Aug 1991

Micellar Catalysis Of Hydrolysis Of Substituted Hydroxamic Acids With Perfluorooctanoic Acid, Zhongyuan He

Master's Theses

The work demonstrated the effects of differently located and substituted phenyl groups, as well as aliphatic groups in the hydroxamic acids, on micellar catalysis with perfluorooctanoic acid as the reactive counterion surfactant in aqueous acetonitrile solution.

Kinetic rate constant-surfactant concentration profiles for the decano-, 2,5-dimethylphenylaceto-, 4-isopropylphenylaceto-, 4-phenylbutano-, and 6-phenyl-hexanohydroxamic acids were examined and analysis on the data obtained were reported.

The pseudo-phase ion exchange (PPIE) model has been satisfactorily applied to explain the observed micellar effects.

Further investigation into more appropriately substituted hydroxamic acids is suggested in order to obtain a more complete set of data and further evaluation.


Micellar Catalyzed Hydrolysis Of Hydroxamic Acids By Perfluorooctanoic Acid, Mohammad Hashem Akhavan Tafti Dec 1988

Micellar Catalyzed Hydrolysis Of Hydroxamic Acids By Perfluorooctanoic Acid, Mohammad Hashem Akhavan Tafti

Master's Theses

The work reported herein demonstrated that a perfluorocarboxylic acid does indeed behave as a reactive counterion surfactant exhibiting micellar catalysis, this conclusion was further verified by subsequent experimentation.

Rates of acidic hydrolysis of octano-, phenylaceto-, and 4-bromo phenylacetohydroxamic acid have been determined in aqueous perfluorooctanoic acid--a reactive counterion surfactant system. Typical micellar catalysis was observed for the hydrolysis of octanohydroxamic acid but not for the arylacetohydroxamic acids.

Further investigation into finding a more water soluble surfactant which has reactive counter ions is suggested in order to test the theoretical equation (based on the pseudo phase model) appropriate for this surfactant ...


A Synthetic Approach To Novel Heterocyclic Herbicides, Paul Antony Pathadan Apr 1988

A Synthetic Approach To Novel Heterocyclic Herbicides, Paul Antony Pathadan

Master's Theses

The purpose of this research study was to prepare novel heterocyclic herbicides. The first phase of the project was to synthesize 1-(nitromethyl)-4-phthalazone.

In the second phase 1 - (nitromethyl)-4-phthalazone was treated with 1,3-propane-dithio-di-p-toluene sulfonate in presence of sodium hydride to get the target compound 4-(1'-nitro-l,3-dithiane)phthalazone.

It is believed that this compound might block the electron transport system of aerobic cells1 . So further investigation of this compound may lead to novel herbicides.


Synthesis And Study Of Novel Quinoxaline Di-N-Oxide And 3-Acyl-2-Methylquinoxaline Di-N-Oxides, Cyprian Okwara Ogbu Apr 1988

Synthesis And Study Of Novel Quinoxaline Di-N-Oxide And 3-Acyl-2-Methylquinoxaline Di-N-Oxides, Cyprian Okwara Ogbu

Master's Theses

This research project consists of two parts. The first involved the synthesis of a novel quininoxaline di-N-oxide via benzofuroxan. The second part was the use of this compound as a synthetic precursor.

It was assumed that 3,4-dimethylaniline would be successfully converted to 5,6-dimethybenzofurazan 1-oxide (5,6-dimethybenzofuroxan) through a sequence of reaction steps. Fortunately, this assumption was correct as the desired compound was produced. This compound was utilized in synthesizing the novel 3-acetyl-2,6,7-trimethylquinoxaline 1,4-dioxide. From the structure of this adduct, it is believed that it will take part in condensation reactions associated with methyl ketones without ...


Synthesis And Reactions Of A-Diketones And Preparation Of Some New Benzimidazoles, Mohamad Reza Agharahimi Apr 1988

Synthesis And Reactions Of A-Diketones And Preparation Of Some New Benzimidazoles, Mohamad Reza Agharahimi

Master's Theses

This report will discuss the synthesis of 2,5-dl-(p-chlorophenyl)-3,4-dioxoadiponitrile and its reactions. This compound exists in the form of 4,4'- dichloropulvinic nitrile which is a precursor to 4,4'-dichk>rovulpinic acid. These compounds have been shown to have antiinflammatory activity in rats.

The benzimidazole and pyridazine derivatives of 4,4'-dichioropulvinic nitrile and the benzimidazole derivative of 4,4'-dichk>rovuipinic acid are another group of compounds that are also believed to have useful biological activities. The Pinner synthesis of imidates is used to make the intermediate to the benzimidazole derivative of 4,4 ...


The Preparation And Reaction Of Novel Glycosyl Ureas And Thioureas, Robert Scott Johnson Apr 1987

The Preparation And Reaction Of Novel Glycosyl Ureas And Thioureas, Robert Scott Johnson

Master's Theses

No abstract provided.


Synthesis Of Pyridine Nucleosides By Cycloaddition Reactions And Synthesis And Condensation Reactions Of 4-Aryl-2-Oxytetronimides, Glenn L. Heise Dec 1985

Synthesis Of Pyridine Nucleosides By Cycloaddition Reactions And Synthesis And Condensation Reactions Of 4-Aryl-2-Oxytetronimides, Glenn L. Heise

Master's Theses

Experiment 1: The reaction of various glutaconaldehyde salts (Na+ or K+) with glycosyl isothiocyanates has resulted in the formation of a novel class of compounds. Relatively mild conditions were utilized for the synthesis which occurs in four steps, and in good yield, starting from glucpseptentaacetate. These reactions were found to be regiospecific. The unique physical and spectral properties of the model compound 1-(2,3,4,6-tetra-0-acetyl-β-D-glycopranosyl)-2-thiono-3-pyridine carboxaldehyde are also discussed.

Experiement 2: Early synthetic methodologies have recently been utilized in the synthesis of 4-aryl-2-oxytetronimides. These compounds have been found to participate in condensation reactions with various substituted o-phenylene ...


Reactivity Of Some Nitrogen-Containing Compounds At Supercritical Water Conditions, David M. Tiffany Apr 1985

Reactivity Of Some Nitrogen-Containing Compounds At Supercritical Water Conditions, David M. Tiffany

Master's Theses

The use of water at cuperctirical conditions to remove nitrogen from several nitrogen-containing compounds was studied with the purpose of exploring the use of supercritical water as a method of removing nitrogen from the extraction products of coal. Quinoline and isoquinolone were the primary model compounds used with benzonitrile and carbazole also being examined briefly. Reaction conditions varied in temperature (350-500°C), pressure (3500-5200 psi), and water density (0.170-.0.426g/cc). The major products formed by isoquinoline were benzene, toluene, ethylbenzene, and o-xylene as well as nonvolatile tar and char. Quinoline produced aniline and toluidine in addition to ...


Heterocyclic Syntheses Utilizing Aryl Cyanates, Joseph Eugene Drumm Iii Dec 1984

Heterocyclic Syntheses Utilizing Aryl Cyanates, Joseph Eugene Drumm Iii

Master's Theses

No abstract provided.


Cationic And Anionic Micellar Catalyzed Hydrolysis Of Hydroxamic Acids, Douglas Eugene Conran Dec 1983

Cationic And Anionic Micellar Catalyzed Hydrolysis Of Hydroxamic Acids, Douglas Eugene Conran

Master's Theses

The hydrolysis of octanohydroxamic and N-methyloctanohydroxamic acids in the presence of cationic and anionic micelles was investigated. Rate constants were determined for the hydrolyses in cetyltrimethylammonium bromide (ctab), the cationic surfactant, with 0.1111 N NaOH and in sodium 1-dodecanesulfonate, the anionic surfactant, with 0.09270 N HC1 at 50.01 + 0.11°C. The acid hydrolysis and the base hydrolysis of N-methyloctanobydroxamic acid followed the standard model for micellar catalysis.