Open Access. Powered by Scholars. Published by Universities.®

Organic Chemistry Commons

Open Access. Powered by Scholars. Published by Universities.®

2,835 Full-Text Articles 3,946 Authors 589,517 Downloads 154 Institutions

All Articles in Organic Chemistry

Faceted Search

2,835 full-text articles. Page 62 of 79.

Water-Soluble Deep-Cavity Cavitands: Synthesis, Molecular Recognition, And Interactions With Phospholipid Membranes, Sarah E. Ioup 2012 University of New Orleans

Water-Soluble Deep-Cavity Cavitands: Synthesis, Molecular Recognition, And Interactions With Phospholipid Membranes, Sarah E. Ioup

University of New Orleans Theses and Dissertations

Water-soluble deep-cavity cavitands provide a rare opportunity to study self-assembly driven by the hydrophobic effect. These molecular hosts dimerize in the presence of certain guest molecules to form water-soluble molecular capsules. These systems have given rise to numerous novel chemical phenomena and have potential use in drug delivery. The host octaacid (OA) has been particularly well-characterized, but studies are limited to basic pH because of limited host solubility.

Herein we report an improved synthesis of OA and the syntheses of three new water-soluble deep-cavity cavitands. The new hosts are soluble at neutral pH, increasing relevance for biological studies. The new ...


Bf2obn∙Oet2: A Novel Lewis Acid And Its Use In A Regio- And Stereo-Selective Opening Of Trisubstituted Epoxides And Its Application Towards Amphidinolide C, Nicholas A. Morra, Brian Pagenkopf 2012 University of Western Ontario

Bf2obn∙Oet2: A Novel Lewis Acid And Its Use In A Regio- And Stereo-Selective Opening Of Trisubstituted Epoxides And Its Application Towards Amphidinolide C, Nicholas A. Morra, Brian Pagenkopf

Chemistry Publications

The generation of a new Lewis acid (BF2OBn·OEt2) has been reported, and its usefulness has been demonstrated in the regio- and stereoselective ring-opening of trisubstituted epoxides. This Lewis acid is one in a series of new Lewis acids generated from BF3·OEt2 that display varying levels of Lewis acidity. When paired with a modified Shi epoxidation protocol, highly functionalized propionate units, such as those found in a wide variety of natural products, can be accessed. In conjunction with a Mukaiyama oxidative cyclization employing our second generation catalyst Co(nmp)2, this procedure ultimately culminated in the shortest and highest ...


Judging A Book By Its Cover: Using Lectin Microarrays To Identify How Glycosylation Is Regulated, John F. Rakus 2012 Marshall University

Judging A Book By Its Cover: Using Lectin Microarrays To Identify How Glycosylation Is Regulated, John F. Rakus

Chemistry Faculty Research

Glycosylation involves the post-translational addition of carbohydrates to protein molecules and is an intricate and indispensable biochemical process. Study of this complicated network of interactions is hindered by the lack of a coding template analogous to the genetic code, and by the vast structural complexity inherent to carbohydrate polymers. We use lectins (non-enzymatic carbohydrate-binding proteins of non-immunological origin) as microarray probes to identify carbohydrate features expressed on cellular surfaces. Specifically, we utilized lectin microarray technology to investigate the differences in carbohydrates expressed by the cell lines of the Nation Cancer Institute’s NCI-60 panel. Our investigation identified tissue-specific expression differences ...


Investigations Of Inter- And Intramolecular C-O Bond Forming Reactions Of Peroxide Electrophiles, Benjamin W. Puffer 2012 University of Nebraska-Lincoln

Investigations Of Inter- And Intramolecular C-O Bond Forming Reactions Of Peroxide Electrophiles, Benjamin W. Puffer

Student Research Projects, Dissertations, and Theses - Chemistry Department

A common reaction to yield ethers relies on an alkoxide nucleophile and a carbon electrophile (Williamson ether formation). Ethers can also be formed by reactions with carbon nucleophiles and oxygen electrophiles by way of the peroxide functional group. We screened a number of carbon nucleophiles suitable for attack on dialkyl peroxides to form new C-O bonds. Also a novel approach using a peroxyketal electrophile is shown to increase the efficiency of this intermolecular reaction. This method of C-O bond formation can also be implemented intramolecularly, not seen before in the literature, to yield cyclic ethers. This approach requires the generation ...


Anti-Germinants As A New Strategy To Prevent Clostridium Difficile Infections, Amber Janece Howerton 2012 University of Nevada, Las Vegas

Anti-Germinants As A New Strategy To Prevent Clostridium Difficile Infections, Amber Janece Howerton

UNLV Theses, Dissertations, Professional Papers, and Capstones

Clostridium difficileinfections (CDI) have emerged as a leading cause of hospital-associated complications. CDI is the major cause of antibiotic-related cases of diarrhea and nearly all cases of pseudomembranous colitis. The infective form of C. difficileis the spore, a dormant and hardy structure that forms under stress. Germination of C. difficile spores into toxin producing bacteria in the GI tract of susceptible patients is the first step in CDI establishment. Patient susceptibility occurs with a disruption of the natural gut microbiota by broad-spectrum antibiotics. Antibiotic treatments usually resolve CDI but refractory cases are on the rise. Of great concern is the ...


Designing Tools For Studying The Dynamic Glycome, John F. Rakus 2012 Marshall University

Designing Tools For Studying The Dynamic Glycome, John F. Rakus

Chemistry Faculty Research

Glycosylation involves the post-translational addition of carbohydrates to protein molecules and is an intricate and indispensable biochemical process. Study of this complicated network of interactions is hindered by the lack of a coding template analogous to the genetic code, and by the vast structural complexity inherent to carbohydrate polymers. We use lectins (non-enzymatic carbohydrate-binding proteins of non-immunological origin) as microarray probes to identify carbohydrate features expressed on cellular surfaces. Specifically, we utilized lectin microarray technology to investigate the differences in carbohydrates expressed by the cell lines of the Nation Cancer Institute’s NCI-60 panel. Our investigation identified tissue-specific expression differences ...


Boron And Metal Catalyzed C-C And C-H Bond Formation, Adam Barret Pippin 2012 University of Tennessee, Knoxville

Boron And Metal Catalyzed C-C And C-H Bond Formation, Adam Barret Pippin

Doctoral Dissertations

Research efforts focused on the use of boron and metals to form new carbon-carbon and carbon-hydrogen bonds are summarized in this dissertation. Several novel reactions have been developed. These include: the deoxygenation of benzylic alcohols using chloroboranes; alkenylation of benzylic alcohols using boron trichloride; and dialkynlation of aryl aldehydes using dialkynylboron chloride. Numerous applications of these novel reactions have been developed. These include alternate routes to diphenylmethanes and 1,4-diynes from easily prepared dialkynylboron chlorides. In addition, E and Z alkenyl halides can now be prepared using boron trichloride without the use of butyllithium. The stereochemistry of the alkenyl halide ...


New Applications Of Mass Spectrometry For Drug And Lipid Analysis, Elizabeth Lauren Emerson 2012 University of Arkansas, Fayetteville

New Applications Of Mass Spectrometry For Drug And Lipid Analysis, Elizabeth Lauren Emerson

Theses and Dissertations

Mass spectrometry is an important tool used in many different disciplines and settings that include forensics, drug discovery, environmental analysis, and proteomics. Gas chromatography - mass spectrometry (GC-MS) and matrix assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI - TOF MS) are two of the most important instruments used for analysis of compounds. Chapters 1 and 2 of this discussion use GC-MS for the investigation of synthetic cannabinoids in `K2' incense products and the detection of metabolites in urine samples from individuals suspected of consuming these mixtures. Analytical standards were synthesized and used for identification and confirmation of structures. Detection of these ...


Part 1. Design And Synthesis Of Cysteine/Cystine Prodrugs And Bioisosteres Including Symmetrical And Unsymmetrical Disulfides Designed To Increase Cystine Levels In The Cns In Order To Drive The Cystine/Glutamate Antiporter: A Novel Treatment For Schizophrenia And Drug Addiction. Part 2. Design And Synthesis Of Subtype Selective Ester Bioisosteres Of Bzr Ligands For Gabaa/Benzodiazepine Receptors To Enhance Metabolic Stability, Edward Merle Johnson II 2012 University of Wisconsin-Milwaukee

Part 1. Design And Synthesis Of Cysteine/Cystine Prodrugs And Bioisosteres Including Symmetrical And Unsymmetrical Disulfides Designed To Increase Cystine Levels In The Cns In Order To Drive The Cystine/Glutamate Antiporter: A Novel Treatment For Schizophrenia And Drug Addiction. Part 2. Design And Synthesis Of Subtype Selective Ester Bioisosteres Of Bzr Ligands For Gabaa/Benzodiazepine Receptors To Enhance Metabolic Stability, Edward Merle Johnson Ii

Theses and Dissertations

Part 1. Schizophrenia is a debilitating disorder that affects almost 1% of the world's population; pharmacotherapy expenditures for this disorder exceed $10 billion dollars even though existing medications exhibit a poor safety/efficacy profile. It is estimated that 75% of patients discontinue drug treatment, in part due to poor safety/efficacy. The current data set demonstrates that cysteine prodrug NAC reverse the behavioral and neurochemical effects of PCP used to model schizophrenia.

As a result cysteine prodrugs represent a highly novel approach to treating schizophrenia; indeed, these compounds may ultimately be more effective than existing medications because these drugs ...


Part I. The First Enantiospecific, Stereospecific Total Synthesis Of The Indole Alkaloid Ervincidine. Part Ii. The Synthesis Of Alpha 5 Subtype Selective Ligands For Gaba(A) /Benzodiazepine Receptors, Sundari K. Rallapalli 2012 University of Wisconsin-Milwaukee

Part I. The First Enantiospecific, Stereospecific Total Synthesis Of The Indole Alkaloid Ervincidine. Part Ii. The Synthesis Of Alpha 5 Subtype Selective Ligands For Gaba(A) /Benzodiazepine Receptors, Sundari K. Rallapalli

Theses and Dissertations

Part I. The first enantiospecific, stereospecific total synthesis of ervincidine 89 has been accomplished from commercially available D-(+)-tryptophan 37 which has served both as the chiral auxiliary and the starting material. Moreover, this is the first synthesis which unequivocally sets the stereochemistry of the hydroxyl group at C-6 in sterospecific fashion, as well as the C-16 hydroxy methyl group. The stereospecific conversion of D-(+)-tryptophan 37 into the key template (−)-Na-H, Nb-benzyl tetracyclic ketone 49 via the asymmetric Pictet-Spengler reaction (600 gram scale) and Dieckmann cyclization on multi-hundred gram scale was reduced to only two reaction vessels. The optically ...


Synthesis, Evaluation And Applications Of Biologically Significant Molecules And Their Analogues, Sneha Ashesh Belapure 2012 University of Tennessee, Knoxville

Synthesis, Evaluation And Applications Of Biologically Significant Molecules And Their Analogues, Sneha Ashesh Belapure

Doctoral Dissertations

Synthetic chemists are always looking for challenging problems to solve. Design and synthesis of novel molecules that can act as agents of chemical and biological modification are one of the foremost goals of a synthetic chemist. This dissertation describes advances and efforts made in this area.

Obesity is one of the critical problems of the modern age. Molecules that can remediate this condition are highly sought after. The first chapter of this dissertation describes synthetic strategies explored to prepare these valuable natural products along with their structural and stereochemical analogues to study structure and activity relationships (SAR). This method gives ...


Phosphorus Transport And Distribution In Kentucky Soils Prepared Using Various Biochar Types, Anvesh Reddy 2012 Western Kentucky University

Phosphorus Transport And Distribution In Kentucky Soils Prepared Using Various Biochar Types, Anvesh Reddy

Masters Theses & Specialist Projects

Conserving the environment is an issue that is gaining popularity day by day. Phosphorus transfer from agricultural soils is an important environmental issue that is being closely observed as the transport of phosphorous to water bodies is adversely affecting water quality due to accelerated eutrophication. It is important to establish phosphorous models that accurately account for soil test phosphorous. Standard models like SWAT (Soil and Water Assessment Tool) and EPIC (Environmental Policy Integrated Climate) were designed for serving this purpose. They are now used as the basis for developing new models that can more accurately account for the phosphorus transport ...


On Metal Synthesis Of Some Substituted Rhenium And Manganese Complexes, Jaron Michael Thomas 2012 Western Kentucky University

On Metal Synthesis Of Some Substituted Rhenium And Manganese Complexes, Jaron Michael Thomas

Masters Theses & Specialist Projects

Heterocyclic organic and organometallic compounds (i.e. polypyrrole), and their derivatives, have been of great interest for conductive polymers due to their novel properties and environmental stability as compared to their non-aromatic analogs (i.e. polyacetylene). Our current interest focus upon the potential role of metal ligand bound pyridazines as the next generation of electronic devices that utilize the metal ligands bound to organics as the semiconducting material. Pyridazine is a 6-membered aromatic ring with two adjacent nitrogen atoms. These are promising candidates for a variety of materials and commercial applications; but they are difficult to get a metal ligand ...


The Use Of Rhenium (Vii) Oxide As A Catalyst For The Substution Of Hemiacetals, Michael W. Richardson 2012 University of Nebraska-Lincoln

The Use Of Rhenium (Vii) Oxide As A Catalyst For The Substution Of Hemiacetals, Michael W. Richardson

Student Research Projects, Dissertations, and Theses - Chemistry Department

Rhenium (VII) oxides have proven to be mild and versatile catalysts in organic chemistry. They have previously been utilized to catalyze the transposition of allylic aclohols, Prins reaction, and reductive amination to name a few examples. This thesis reports the application of Re(VII) oxide in the substitution of hemi-acetals with a wide array of nucleophiles including oxo-, thio-, and peroxy-nucleophiles. These reactions proceed efficiently with rapid reaction times and high yields.

Adviser: Patrick H. Dussault


Controlled Degradation Of Poly(Ester Amide)S Via Cyclization Of Pendant Functional Groups, Jose Samuel Mejia 2012 The University of Western Ontario

Controlled Degradation Of Poly(Ester Amide)S Via Cyclization Of Pendant Functional Groups, Jose Samuel Mejia

Electronic Thesis and Dissertation Repository

Polyesters have been used for many biomedical applications ranging from sutures to drug delivery vehicles. However, their bulk degradation results in an accumulation of acidic byproducts, which is detrimental to the human body. In order to circumvent this problem, as well as to impart new properties and functions to polymers for biomedical applications, poly(ester amide)s (PEAs) have been proposed as a different class of biodegradable polymers. However, up to date, there exists no way to stimulate the degradation of these polymers.

The Gillies research group has previously incorporated self-immolative spacers into polymers and has been able to stimulate ...


Preparation Of Nitrogen-Containing Heterocycles Via Cyclization Of Pyridine-Tethered Organolithiums, Elizabeth Archer 2012 University of Connecticut - Storrs

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

Master's Theses

No abstract provided.


Spectral Data For "Reactivity Of Acyclic (Pentadienyl)Iron(1+) Cations: Synthetic Studies Directed Toward The Frondosins", Do W. Lee, Rajesh K. Pandey, Sergey V. Lindeman, William A. Donaldson 2012 Marquette University

Spectral Data For "Reactivity Of Acyclic (Pentadienyl)Iron(1+) Cations: Synthetic Studies Directed Toward The Frondosins", Do W. Lee, Rajesh K. Pandey, Sergey V. Lindeman, William A. Donaldson

Natural Products Synthesis via Organoiron Methodology

Spectral data created in the course of the research project. Supports specific findings in "Reactivity of acyclic (pentadienyl)iron(1+) cations: Synthetic studies directed toward the frondosins".

A short, 4-step route to the scaffold of frondosin A and B is reported. The [1-methoxycarbonyl-5-(2′,5′-dimethoxyphenyl)pentadienyl]Fe(CO)3+ cation was prepared in two steps from (methyl 6-oxo-2,4-hexadienoate)Fe(CO)3. Reaction of this cation with isopropenyl Grignard or cyclohexenyllithium reagents affords (2-alkenyl-5-aryl-1-methoxycarbonyl-3-pentene-1,5-diyl)Fe(CO)3 along with other addition products. Oxidative decomplexation of these (pentenediyl)iron complexes, utilizing CuCl2, affords 6-aryl-3-methoxycarbonyl-1,4-cycloheptadienes via the presumed ...


Scanning Angle Plasmon Waveguide Resonance Raman Spectroscopy For The Analysis Of Thin Polystyrene Films, Matthew W. Meyer, Kristopher J. McKee, Vy H.T. Nguyen, Emily A. Smith 2012 Iowa State University

Scanning Angle Plasmon Waveguide Resonance Raman Spectroscopy For The Analysis Of Thin Polystyrene Films, Matthew W. Meyer, Kristopher J. Mckee, Vy H.T. Nguyen, Emily A. Smith

Chemistry Publications

Scanning angle (SA) Raman spectroscopy was used to characterize thin polymer films at a sapphire/50 nm gold film/polystyrene/air interface. When the polymer thickness is greater than ∼260 nm, this interface behaves as a plasmon waveguide; Raman scatter is greatly enhanced with both p- and s-polarized excitation compared to an interface without the gold film. In this study, the reflected light intensities from the interface and Raman spectra were collected as a function of incident angle for three samples with different polystyrene thicknesses. The Raman peak areas were well modeled with the calculated mean-square electric field (MSEF) integrated ...


One-Pot Three-Step Thioconjugate Addition-Oxidation-Diels–Alder Reactions Of Ethyl Propiolate, C. Wade Downey, Smaranda Craciun, Christina A. Vivelo, Ana M. Neferu, Carly J. Mueller, Stephanie Corsi 2012 University of Richmond

One-Pot Three-Step Thioconjugate Addition-Oxidation-Diels–Alder Reactions Of Ethyl Propiolate, C. Wade Downey, Smaranda Craciun, Christina A. Vivelo, Ana M. Neferu, Carly J. Mueller, Stephanie Corsi

Chemistry Faculty Publications

Ethyl propiolate undergoes one-pot three-step thioconjugate addition-oxidation-Diels–Alder cycloaddition when treated with a variety of thiols in the presence of catalytic base, meta-chloroperbenzoic acid, lithium perchlorate, and cyclopentadiene. The reaction of S‑aryl thiols is catalyzed by trialkylamines, and the reaction of aliphatic thiols requires catalytic alkoxide base. Yields of the major diastereomer of the conveniently functionalized bicyclic products range from 47 to 81% depending upon the thiol reactant, which compares favorably to yields observed when the entire synthesis is performed step by step.


One-Pot Synthesis Of (Z)-B-Sulfonyl Enoates From Ethyl Propiolate, C. Wade Downey, Smaranda Craciun, Ana M. Neferu, Christina A. Vivelo, Carly J. Mueller, Brian C. Southall, Stephanie Corsi, Eric W. Etchill, Ryan J. Sault 2012 University of Richmond

One-Pot Synthesis Of (Z)-B-Sulfonyl Enoates From Ethyl Propiolate, C. Wade Downey, Smaranda Craciun, Ana M. Neferu, Christina A. Vivelo, Carly J. Mueller, Brian C. Southall, Stephanie Corsi, Eric W. Etchill, Ryan J. Sault

Chemistry Faculty Publications

B-Sulfonyl enoates may be synthesized through a one-pot two-step sequence from ethyl propiolate with good to excellent selectivity for the Z isomer. Trialkylamines catalyze thioconjugate additions of aryl thiols, and alkoxides catalyze the addition of aliphatic thiols. Addition of meta-chloroperbenzoic acid (mCPBA) and LiClO4 to the reaction mixture provides rapid access to the sulfonyl enoates. Yields of the pure Z isomer range from 51 – 90%.


Digital Commons powered by bepress