Chemistry Commons^™

Regioselective Catalytic Synthesis Of Potentially Bioactive 1,3,4-Selenadiazole, Mohamed Ali Mahmoud

Theses

Isoselenocyanates have a crucial role as reactants in chemical processes, facilitating the efficient synthesis of significant chemical intermediates and physiologically active chemicals. The utilization of (Z)-2-oxo-N-phenylpropanehydrazonoyl chlorides in a one-step procedure for the synthesis of the core structure of various heterocyclic compounds has been widely explored. This study focuses on the synthesis of 5-arylimino-1,3,4-selenadiazole derivatives through the reaction of isoselenocyanates with various substituted (Z)-2-oxo-N-phenylpropanehydrazonoyl chlorides. The objective is to achieve selective and accurate formation of these derivatives. The derivatives exhibit a diverse range of functional groups on both aryl rings. The synthetic procedure is conducted under ambient conditions, promoting environmental …

Synthesis Of Alnustone-Like Diarylpentanoids Via A 4 + 1 Strategy And Assessment Of Their Potential Anticancer Activity, Nesli̇han Çelebi̇oğlu, Özlem Özdemi̇r Tozlu, Hasan Türkez, Hasan Seçen

Turkish Journal of Chemistry

Twelve compounds with a 1,5-diaryl-1-penten-3-one structure were synthesized and their cytotoxic activities were evaluated. The 1,5-diaryl-1-penten-3-one compounds were obtained via in situ enaminations of 4-phenyl-2-butanone and 4-(4-hydroxyphenyl)-2- butanone in the presence of pyrrolidine-AcOH, followed by condensation with six different benzaldehydes. The synthesized compounds were tested for their cytotoxic activity against human glioblastoma (U87-MG), breast (MCF-7), and prostate (PC-3) cancer cell lines. Some of the novel compounds exhibited remarkable cytotoxic action, especially against MCF-7 cancer cells.

Enabling Technologies For Chemical Synthesis: I. Selective Microwave Heating; Ii. Synthesis And Regioselective Cyclotrimerizations Of Tethered 1,6-Diynes, Amir Tavakoli

Graduate Theses, Dissertations, and Problem Reports

Reaction discoveries, method developments, and technology advancements lie at the heart of synthetic organic chemistry. These innovations are essential for creating and manipulating complex molecules, which are the building blocks of many important chemical compounds, including pharmaceuticals, materials, and agrochemicals. Here, we first describe new methods to prepare neopentylene-tethered (NPT) 1,6-diynes which are valuable substrates for reaction discovery and target-oriented synthesis, especially in benzannulation strategies toward illudalane natural products. NPT 1,6-diynes have been employed as coupling partners in cyclotrimerization reactions for the synthesis of highly substituted benzene rings which present a persistent challenge in chemical synthesis and are underrepresented scaffolds …

The Affect Of Dha Concentration On Lipid Membrane Fluidity, Elise Rezabeck

Williams Honors College, Honors Research Projects

My proposed project will be creating large unilaminar vesicles with varying concentrations of DHA in the vesicles. The diffusion in and out of these vesicles will be tracked by using singular lipid molecules. These singular lipid molecules will be tagged with fluorescence and viewed using an internal reflection fluorescence microscope. The data collected over the course of this project will then be analyzed using Matlab. The result of the project will be to find the specific lipid diffusion constant of these unilaminar vesicles. The relationship between the concentration of DHA and lipid diffusion and membrane fluidity will be found as …

Global Minimum Search For The Largest Ge Cage Stabilized By A Single Interstitial Metal Atom, Alexis Kiefer

Williams Honors College, Honors Research Projects

Recent joint experimental and theoretical studies showed that the largest Ge cage-like cluster features 14 Ge atoms that encapsulate a single transition metal atom in the [Nb@Ge₁₄]^3- cluster. The next larger experimentally confirmed Ge cluster exhibiting a cage-like geometry was found to be viable only when stabilized by two transition metal atoms in the [Co₂@Ge₁₆]^4- cluster. So, as of now, it is not clear whether a cage-like cluster made out of 15 Ge atom stabilized by a single transition metal is viable. Hence, the aim of this project is to find the …

Synthesis And Cyclotrimerization Of Sulfonyl Enynes, Alexa C. Martin

Graduate Theses, Dissertations, and Problem Reports

The synthesis of complex, polysubstituted aromatic rings from simple, non-aromatic building blocks is a consistent challenge to the synthetic community. Neopentylene ring fusions are found in several natural products but are largely absent from synthetic compound libraries. This discrepancy reflects the limitations in modern chemical synthesis. Utilizing, in part, a thoroughly developed fragmentation/olefination methodology from the Dudley Lab, a library of novel 1-sulfonyl-1,6-enynes have been developed. In this methodology, they are prepared in three steps from dimedone (5,5-dimethyl-1,3-cyclohexanedione), an inexpensive starting material. A total of 14 novel 1-sulfonyl-1,6-enynes were synthesized. These substrates were subjected to a novel benzannulation reaction based …

Sequential Block Copolymers Of Polyisobutylene And Polyolefins, Manwel Labib

Williams Honors College, Honors Research Projects

A two-step approach will be utilized to synthesize random polyolefin multiblock-copolymers. This strategy takes advantage of a,w-terminated telechelic polyolefins. Polypropylene (iPP)/polyethylene (PE) are picked because of their strength, and polyisobutylene (PIB) because of its hemocompatibility. This copolymer is theorized to make for robust bio-inert plastic, which can be used for surgical mesh implants.

1,2-Diamination Of Alkenes Via Reduction Of 1,2,3-Triazolinium Ions, Setareh Saryazdi

Theses and Dissertations--Chemistry

1,2-Diamine substructures are prevalent functional motifs in natural products, pharmaceutical compounds, and ligands. The interesting functionalities of 1,2-diamines have inspired many synthetic chemists to design various methodologies for preparing these structures from simple precursors such as alkenes. In this work, we described two different but related methods using simple and easily accessible reagents for 1,2-diamination of alkenes. In the first method, an alkene undergoes 1,3-dipolar cycloaddition with an organic azide to form a 1,2,3-triazoline. Subsequent N-alkylation of the generated 1,2,3-triazoline gives the 1,2,3-triazolinium ion, which is then hydrogenated over Raney Ni with a balloon of H₂ to produce …

Synthesis Of 2-Aryl-5-(Arylsulfonyl)-1,3,4-Oxadiazoles As Potent Antibacterial Andantioxidant Agents, S N Murthy Boddapati, Subrahmanyam Talari, A Emmanuel Kola, Bhuvaneswari Chalapaka

Turkish Journal of Chemistry

Ten novel 2-aryl-5-(arylsulfonyl)-1,3,4-oxadiazoles were produced and assessed for their in vitro antibacterial and antioxidant activities. Diverse spectroscopic methods li1H NMR, 13C NMR, IR, and LCMS were used for the characterization of the prepared samples and all the data was in good agreement with the anticipated structures. The prepared compounds 6a-j were screened for their in vitro antibacterial activity against bacterial strains Pseudomonas aeruginosa, Enterobacter aerogenes, Escherichia coli (grampositive), and Bacillus cerus, Staphylococcus aureus, Bacillus subtilis (gram-negative). The antimicrobial screening outcome revealed that the prepared 2-(3,4-dimethylphenyl)-5-tosyl-1,3,4-oxadiazole (6j), 2-(3-isopropylphenyl)-5-tosyl-1,3,4-oxadiazole (6c), and 2-(2-ethylphenyl)-5-tosyl-1,3,4-oxadiazole (6i) are most potent among all the examined compounds. Furthermore, …

Synthesis Of Novel Oxadiazole Derivatives And Their Cytotoxic Activity Against Various Cancer Cell Lines, Bi̇lgesu Onur Sucu, Eli̇f Beyza Koç

Turkish Journal of Chemistry

Caffeic acid (CA), ferulic acid (FA) and caffeic acid phenethyl ester (CAPE) have a broad anticancer effect on various cell lines. In this study, nine ferulic and caffeic acid-based 1,2,4 and 1,3,4 oxadiazole molecular hybrids were synthesized and their cytotoxic activity was evaluated mainly against Glioblastoma (GBM) cell lines. Compounds 1 and 5 exhibited the highest inhibitory activity against three different GBM cell lines (LN229, T98G, and U87), without toxicity to healthy human mesenchymal stem cells (hMSC). In addition, their cytotoxicity was also evaluated against three additional cancer cell lines and more inhibitory results were found than GBM cell lines. …

1,2-Diazetidine As A New Amidomethylative Reagent To Control The Selectivity For The Synthesis Of N-Heterocycles And Ru(Ii)-Catalyzed Enantioselective Hydroarylation To Form Chromane Derivatives, Chaminda Lakmal Hetti Handi

Theses and Dissertations

1,2-Diazetidine is a four-membered ring heterocyclic compound which has two adjacent nitrogen atoms. However, the syntheses of C-unsubstituted 1,2-diazetidines are rarely reported in the literature. C-unsubstituted 1,2-diazetidines were synthesized through an operationally simple intermolecular vicinal disubstitution reaction between 1,2-dibromoethane and hydrazine with N-arylsulfonyl as the protecting group. Several different types of C-unsubstituted 1,2-diazetidines derivatives were synthesized with either two of the same or two different N-arylsulfonyl groups. The electronic and steric properties were analyzed using Raman spectroscopy and computational calculations. Then, several synthetic applications were demonstrated with 1,2-ditosyl-1,2-diazetidine (DTD). As a synthetic application, a nucleophilic ring-opening reaction of the diazetidine …

Synthesis And Characterization Of Re(I) Tricarbonyl Complexes Of 1,8-Naphthalimide, Priyanka Jagadeesa Prabhu

Electronic Thesis and Dissertation Repository

1,8-Naphthalimide fluorophores with amino-substituents absorb and emit in the visible region. The photophysical properties of this class of fluorophores can be modulated by altering the degree of Intramolecular Charge Transfer (ICT) in the excited state. Thus, several metal complexes with the 1,8-naphthalimide motif have been developed as cell imaging agents. In this project, four 1,8-naphthalimide ligands were synthesized by incorporating rigid linkers. Among these, three ligands also allowed the extension of π-conjugation to the naphthalimide moiety. In addition, a ligand was also synthesized without the use of a linker. Re(I) tricarbonyl complexes of these ligands were also synthesized and their …

A Multifunctional Solution Composed Of Tmpyp, 1,5-Dhn, And Fe(Iii) Ions That Produces Reactive Oxygen Species (Ros) In Aerobic, Anaerobic, And H2o2 Environments, Aqeeb Ali

Electronic Theses and Dissertations

Photodynamic therapy (PDT) has become a widely popular therapeutic approach for treating various types of cancer over the past several decades. PDT utilizes a photosensitizer, visible light, and oxygen, to produce reactive oxygen species (ROS) which can be used to treat cancer and inhibit growth of bacteria. In this study, a multifunctional solution that is comprised of Fe(III) ions, cationic meso-tetra(N-methyl-4-pyridyl)porphine tetrachloride (TMPyP), and 1,5-dihydroxynapthalene (1,5-DHN), was shown to produce reactive oxygen species (ROS) such as singlet oxygen (¹O₂) or hydroxyl radicals (ȮH) in aerobic or anaerobic environments, respectively, and in both environments, 1,5-DHN was oxidized …

Integrated 3d-Qsar, Molecular Docking, And Molecular Dynamics Simulation Studies On 1,2,3-Triazole Based Derivatives For Designing New Acetylcholinesterase Inhibitors, Khalil El Khatabi, Ilham Aanouz, Reda El-Mernissi, Atul Kumar Singh, Mohammed Aziz Ajana, Tahar Lakhlifi, Shashank Kumar, Mohammed Bouachrine

Turkish Journal of Chemistry

Alzheimer's disease (AD) is a multifactorial and polygenic disease. It is the most prevalent reason for dementia in the aging population. A dataset of twenty-six 1,2,3-triazole-based derivatives previously synthetized and evaluated for acetylcholinesterase inhibitory activity were subjected to the three-dimensional quantitative structure-activity relationship (3D-QSAR) study. Good predictability was achieved for comparative molecular field analysis (CoMFA) (Q2 = 0.604, R2 = 0.863, rext2 = 0.701) and comparative molecular similarity indices analysis (CoMSIA) (Q2 = 0.606, R2 = 0.854, rext2 = 0.647). The molecular features characteristics provided by the 3D-QSAR contour plots were quite useful for designing and improving the activity of …

Synthesis, Spectral Characterization, And Biological Studies Of 3,5-Disubstituted- 1,3,4-Oxadiazole-2(3h)-Thione Derivatives, Tuğçe Özyazici, Fi̇kretti̇n Şahi̇n, Meri̇ç Köksal Akkoç

Turkish Journal of Chemistry

The reaction of 3,4-dichlorophenyl-1,3,4-oxadiazole-2(3H)-thione with piperidine derivatives via Mannich reaction was used to generate eleven novel compounds in moderate to good yields. Synthesized molecules were characterized according to their structure with 1H NMR, 13C NMR and FT-IR spectral foundations, which were compatible with literature informations. Antimicrobial activity and cytotoxicity studies were done by disc diffusion and NCI-60 sulphordamine B assay methods. The antimicrobial test results revealed that synthesized compounds have better activity against gram-positive species than gram-negative ones. A total analysis of the antibacterial, antifungal, and antiyeast activity revealed that newly synthesized compounds were really active against Bacillus cereus, Bacillus …

The Rotational Spectrum Of 1,1-Diiodoethane, Michael Joseph Carrillo

Theses and Dissertations

The first chapter of this thesis introduces the basic theory of rotational spectroscopy. This includes the theory of a rigid rotor, centrifugal distortion, and hyperfine effects. The theory behind diatomic systems is explained first, and then expanded to the asymmetric top system. The second chapter encompasses a brief overview on the development of microwave spectroscopy and discusses the instruments that were utilized during this study, namely the cavity-based and chirped-pulse Fourier transform microwave spectrometers. Chapter three describes the quantum chemical calculation methods and basis sets that were applied throughout this study. Chapter four discusses the progress of data analysis of …

Synthesis And Characterization Of Novel Derivatives Of 1, 3, 4- 0xadiazole And Isoniazid, Ranem Mohammad Kaddoura

Chemistry Theses

This thesis describes the synthesis of novel derivatives of isoniazid and 1, 3, 4- oxadiazole piperazines and biological activities evaluation. The synthesis of the isoniazid derivatives (36a-Ɩ) was achieved by nucleophilic substitution of chloroacetylated isoniazid 34 with substituted piperazines (35a-Ɩ) produced isoniazidpiperazines (36a-Ɩ). On the other hand, cyclodehydration of chloroacetylated isoniazid 34 with POCl3 give the corresponding 1, 3, 4-oxadiazole 37 which upon treatment with substituted piperazines (35a-m) gave 1, 3, 4-oxadiazole-piperazines (38a-m). All newly synthesized compounds were purified and characterized using spectroscopic techniques including 1H-NMR, 13C-NMR, IR spectrometry and mass spectrometry.

The biological activity of the synthesized compounds has …

Investigation Of The Intramolecular 1,3-Diaza-Claisen Rearrangement In The Ring Expansion Reactions Of Vinyl Pyrrolidines And Vinyl Piperidines, Teruki Watanabe

Graduate College Dissertations and Theses

The 1,3-diaza-Claisen rearrangement was discovered and developed in the Madalengoitia group since 2004. The rearrangement is initiated by the desulfurization of the electron deficient thiourea and isothiourea to obtain the highly electrophilic carbodiimide which can be reacted with an allylic tertiary amine to form the zwitterionic intermediate which then undergoes [3,3]-sigmatropic rearrangement. Previous investigation includes multiple examples of successful formation of complex guanidines through intermolecular and intramolecular variants. Providing an easy access to guanidine which is one of the most prevalent functional groups in the biologically relevant system, the rearrangement can be a valuable tool in the organic synthesis.

The …

Exploration Of Cis-1,2-Diaminocyclohexane-Based Conformationally Locked Chiral Ligands In Asymmetric Synthesis, Carim Van Beek

University of the Pacific Theses and Dissertations

Natural products have been demonstrated to be of great significance to the pharmaceutical industry in the development of new drugs and medicine. Unfortunately, synthetic approaches to obtain these natural products often prove increasingly challenging due to the complexity of synthesizing the target drug in the proper stereochemistry. The availability of enantioselective reactions can play a pivotal role in overcoming this challenge, yielding access to optically pure intermediates and products. Chiral ligands based on a trans-1,2-diaminocyclohexane motif are often employed for this purpose and their complexes with transition metals have been demonstrated to act as efficient chiral catalysts in asymmetric reactions. …

Synthesis, Characterization And Crystal Structures Of Platinum(Ii) Saccharinate Complexes With 1,5-Cyclooctadiene, Ceyda İçsel

Turkish Journal of Chemistry

Two new platinum(II) complexes, namely [PtCl(sac)(COD)] (1) and [Pt(sac)$_{2}$(COD)] (2) (sac $=$ saccharinate and COD $=$ 1,5-cyclooctadiene), were synthesized and characterized by elemental analysis, IR, NMR, ESI-MS spectroscopic and thermal analysis (TG/DTA) methods. The platinum(II) complexes were prepared from the reaction of [PtCl$_{2}$(COD)] with Na(sac) • 2H$_{2}$O. The addition of the sac ligand resulted in the replacement of 1 and 2 chlorido ligands in [PtCl$_{2}$(COD)] to yield 1 and 2, respectively. The structures of the complexes were determined by single crystal X-ray diffraction and showed a distorted square planar coordination geometry around platinum(II). COD acted as a $\pi $-donor ligand, …

Dna Recovery From Handwritten Documents Using A Novel Vacuum Technique, Patrick M. Mclaughlin

Student Theses

Investigations of many crimes such as robberies, kidnappings, and terrorism are often associated with the recovery of a paper document which has been written by the perpetrator. Paper can provide a variety of forensic evidence such as DNA, latent fingermarks, and indented writing. The focus of this study was the collection of probative DNA profiles from the text region of a handwritten note through a vacuum suction device without altering or destroying the document. Collection of DNA evidence was carried out in two separate groups. The first group involved 11 volunteers providing a handwritten note sample with unwashed hands. The …

Mechanistic Studies And Derivative Effects In 1, 3, 4- Oxadiazole Synthesis Via Cyclodehydration Reactions, Evan Huggins

Undergraduate Honors Thesis Projects

In the world of pharmaceutical synthesis, research to combat foreign pathogens is always necessary. Scientists have been exploring different methods in order to synthesize the most effective compounds in antibacterial, anticancer, anti-inflammatory, and many other treatments. A key component within these versatile compounds are 1,3,4-oxadiazoles. Current methods to synthesize these compounds are inefficient. This research seeks to improve oxadiazole synthesis; however, the mechanism of this reaction is unknown. The goal of this project was to study the mechanistic pathway in the discovered, one-pot cyclodehydration synthesis of 1,3,4-oxadiazoles. In the first part of this study, a diacylhydrazine intermediate was proposed. This …

Design, Synthesis, And Evaluation Of The Antimycobacterial Activity Of 3-Mercapto-1,2,4-Triazole--Pyrrole Hybrids, Gheorghe Roman, Andra-Cristina Bostanaru, Valentin Nastasa, Mihai Mares

Turkish Journal of Chemistry

A series of 3-mercapto-1,2,4-triazole--pyrrole hybrids was designed as antimycobacterial agents by employing 5-(4-(1$H$-pyrrol-1-yl)phenyl)-4$H$-1,2,4-triazole-3-thiol as the scaffold onto which several types of moieties were introduced in the triazole ring at N-4 and N-2 and as substituents of the mercapto function. The aforementioned moieties are an allyl or a phenyl moiety at N-4; an aminomethyl group at N-2; or methyl, substituted benzyl, ethoxycarbonylmethyl, or substituted phenacyl at sulfur. Investigation of the compounds in the resulting library as growth inhibitors of Mycobacterium smegmatis showed that their minimum inhibitory concentration was higher than 64 mg/L.

Characterization And Purification Of 1,2,4-Triazole-Containing Phthalocyanines Synthesized By Microwave Method And Structure Elucidation By Spectroscopic Techniques, Asi̇ye Nas, Ümi̇t Demi̇rbaş, Nurhan Gümrükçüoğlu, Hali̇t Kanteki̇n

Turkish Journal of Chemistry

The complexes of peripherally tetra-substituted metal-free (8), lead(II) 9), and zinc(II) (10) phthalocyanine derivatives were synthesized for the first time in this work. The structures of these new complex compounds have been elucidated using many spectral methods such as electronic absorption, FT-IR, $^{1}$H NMR, $^{13}$C NMR, elemental analysis, and mass spectra. The thermogravimetric behavior of compounds 8-10 was determined by thermogravimetric analysis method in addition to these spectral methods.

1,2-Dibromotetrachloroethane: An Efficient Reagent For Many Transformations By Modified Appel Reaction, Selçuk Eşsi̇z, Ari̇f Daştan

Turkish Journal of Chemistry

An efficient and facile method has been developed for the synthesis of alkyl bromides from various alcohols under mild conditions using a triphenylphosphine (PPh$_{3})$/1,2-dibromotetrachloroethane (DBTCE) complex in excellent yields and very short time (5 min). This method can also be applied for the transformation of chiral alcohols to their corresponding bromides in very high enantiomeric excess. The PPh$_{3}$/DBTCE complex is also successfully applied to ring-opening reactions of cyclic ethers in mild conditions. Esterification, amidation, and formation of acid anhydrides under very mild experimental conditions are also successfully accomplished by following a modification of the Appel reaction protocol in this work.

Crystal Structure And Hirshfeld Surface Analysis Of 1,2-Ethylene-Bis (Para-Methyl Pyridinium) Dichromate As A New Selective And Mild Agent In Oxidation Of Alcohols, Mostafa Gholizadeh, Mehrdad Pourayoubi, Mohammad Reza Houssiendokht, Hadi Amiri Rudbari, Masoumeh Farimaneh, Anahid Saneei, Giuseppe Bruno

Turkish Journal of Chemistry

1,2-Ethylene-bis(para-methyl pyridinium) dichromate, (C$_{14}$H$_{18}$N$_{2})$[Cr$_{2}$O$_{7}$], is used as a new oxidizing agent in conversion of some alcohols to their corresponding carbonyl compounds in CH$_{3}$CN solvent and also under solvent-free conditions. In both procedures, high conversion percentages are observed. However, a much shorter reaction time is achieved in solvent-free conditions. For allylic alcohols, the C=C bond is not oxidized and the examined saturated alcohol in this work (i.e. cyclo-hexanol) remains intact, which illustrates the mild nature of reagent used. The structure of the reagent is investigated by single-crystal X-ray diffraction analysis. The C--H$\cdots$O and O$\cdots \pi$ interactions are the most important features …

An Efficient Protocol For The Synthesis Of Brominated Norbornene, Norbornadiene, And Benzonorbornadiene, Selçuk Eşsi̇z

Turkish Journal of Chemistry

An efficient protocol for the synthesis of 2-bromonorbornene, 2-bromonorbornadiene, 2-bromoben- zonorbornadiene, 2,3-dibromonorbornene, 2,3-dibromonorbornadiene, and 2,3-dibromobenzonorbornadiene in good yields has been developed. 1,2-Dibromotetrachloroethane is used as the brominating agent for these reactions. The results are discussed in comparison with alternative methods in the literature.

Synthesis And Bioactivity Of Sulfide Derivatives Containing 1,3,4-Oxadiazole And Pyridine, Gang Yu, Shunhong Chen, Feng He, Dexia Luo, Yu Zhang, Jian Wu

Turkish Journal of Chemistry

A series of novel sulfide derivatives containing 1,3,4-oxadiazole and pyridine were synthesized, characterized, and tested for their antibacterial activity against tobacco bacterial wilt and rice bacterial blight and for insecticidal activity toward diamondback moth. The results showed that some compounds had good insecticidal and bactericidal activity, e.g., the activities of compounds 6e and 6g-6j toward tobacco bacterial wilt were much better than those of commercial thiodiazole-copper, and some of the synthesized compounds possessed good insecticidal activity against Plutella xylostella. Compounds 6d, 6h, 6j, 6l, 6p, 6r, and 6p displayed over 93% activity at 500 mg L$^{-1}$.

Computational Study Of Lawesson’S Reagent Mediated Fluorenone Dimerization Forming 9,9’-Bifluorenylidene, Andrew Jourdan Eckelmann

MSU Graduate Theses

The ambition of this work is to start a path to the a priori rational design of high yield production for electron acceptors with finely tuned band gaps, from the comfort of an armchair. To this end, organic photovoltaics offer a cheap and sustainable means of manufacture using readily available materials and avoids the toxicity of some of the heavy metals used in first and second-generation solar cells such as cadmium. The microwave assisted Lawesson’s reagent mediated one-pot one-step solventless synthesis takes less than 3 minutes and results in an 84% yield of 9,9’-bifluorenylidene from two equivalents of fluorenone. While …

Synthesis Of Oxadiazoles And Examination Of Steric Effects In A Cyclodehydration Reaction, Norah Young

Undergraduate Honors Thesis Projects

The objective of this project is to develop a general substrate scope by testing various steric and electronic effects. This is pursued by developing triphenylphosphine dibromide (PPh3Br2) as an effective cyclodehydration reagent for use with a variety of hydrazides and sterically and electronically different benzoic acids. The two phases of the experiment include assessing yield through a cyclodehydration reaction and comparing that yield to the steric hindrance and molecular structure recorded in different databases. The cyclodehydration reaction uses ortho-substituted benzoic acid with store bought PPh3Br2, and compares those yields to the use of a two step-one pot reaction in place …