Chemistry Commons^™

Ni2-Imido Bispincer Platforms: Cooperative Reactivity Enabled Through Substrate Addition Across A Ni2n Unit, David De Los Santos, Kritika Gour, Manar M. Shoshani

School of Integrative Biological & Chemical Sciences Faculty Publications

Transition metal imido complexes are renowned for their capacity to undertake challenging 1,2 additions owing to the high basicity of the imido moiety. Access to transition metal imidos is often limited to the addition of organic azides to metal precursors, hindering the design of molecular constructs incorporating imido units. Bimetallic bispincer complexes, 1 and 2, are presented, which are anchored by a central imido moiety supported by pyridyl imine donors, forming highly planarized Ni2N-aryl cores. Complex 2, which also features a Ni─Ni σ-bond, is able to engage in cooperative substrate cleavage of main group hydrides via a formal 1,2 addition …

Salicylic Acid Heterocyclic Derivatives: Chemical Synthesis And Biological Activity, Rawaa Hefdi Zaooli, Marwa Abdulameer Mseer, Amneen Mohammed Alsayegh

Al-Bahir

Before a drug can be widely used, it must go through a long development process, starting from the discovery of the active ingredient and continuing with tests to confirm its safety and effectiveness. In this study, new olsalazine derivatives were synthesized, containing a fused morpholine-3-one ring and two five-membered heterocyclic rings (thiadiazole and oxadiazole). Common and readily available materials, such as salicylic acid (to prepare 2-hydroxy-5-nitrobenzoic acid) and inexpensive catalysts, were used to synthesize compounds from the first, 5,5'-(diazene-1,2-diyl)bis(2-hydroxy-3-nitrobenzoic acid) (A1), to the seventh, 6,6'-(diazene-1,2-diyl)bis(N-(4-(5-amino-1,3,4-oxadiazol-2-yl)phenyl)-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxamide) (A7).

Each compound was characterized by FT-IR and ¹H-NMR spectroscopy, along with physical properties such …

Functionalized 2d Hexaazatriphenylene As Hydrogen Storage Platform: A Dft-Guided Design Approach, Islam Gomaa

Nanotechnology Research Centre

No abstract provided.

The Development Of A One Pot, Two Reaction Synthetic Preparation Of 1,2,4-Oxadiazole, And Synthesis Of Ataluren, A Novel Drug In The Fight Against Duchenne Muscular Dystrophy. Efforts Towards The Synthesis Of A Potential Protease Inhibitor Against The Main Protease (3clpro) Of Covid-19, Austin J. Carter

Theses and Dissertations

1,2,4-Oxadiazoles are five-membered heterocyclic structures first synthesized by Tiemann and Krüger in 1884. Recent discoveries suggest an array of useful biological properties.In preparation of 1,2,4-oxadiazoles, the most prevalent precursors are amidoximes, which can be created via the reaction of nitriles with hydroxylamine hydrochloride and a base. The amidoximes are reacted with an activated carboxylic acid to yield an acylated intermediate. This intermediate can be exposed to a base to cyclize into the 1,2,4-oxadiazole. This thesis describes the efforts in combining these three steps into a unified one-pot synthesis.

Currently, there are a significant number of commercially available FDA approved and …

Approaches To The Synthesis Of Highly Substituted Arenes, Kh Tanvir Ahmed

Graduate Theses, Dissertations, and Problem Reports (ETD)

While benzene rings and their derivatives are among the most frequently encountered ring systems in natural products, pharmaceuticals, agrochemicals, dyes, and functional materials, polysubstituted arenes are relatively scarce. The analysis of FDA-approved small molecules provides valuable insights into the characteristics of successful drugs while also highlighting gaps in the availability of synthetic methods capable of efficiently accessing diverse substitution patterns on aromatic rings. Highly substituted arenes are typically synthesized through sequential modification of a pre-existing benzene core; however, this stepwise approach becomes increasingly challenging with each additional substitution. An alternative strategy involves the direct construction of benzene rings via annulation …

Synthesis And Characterization Of New Hexahydroquinoline Derivatives, Evaluation Of Their Cytotoxicity, Intracellular Ros Production And Inhibitory Effects On Inflammatory Mediators, Ezgi̇ Pehli̇vanlar, Deni̇z Arca Çakir, Sonia Sanajou, Hülya Tezel Yalçin, Terken Baydar, Pinar Erkekoğlu, Hani̇fe Avci, Rahi̇me Şi̇mşek

Turkish Journal of Chemistry

Inflammation is a response to injury and infection in the organism. It can be categorized as acute and chronic inflammation. Chronic inflammation is the underlying cause of many diseases such as Alzheimer's, diabetes, rheumatoid arthritis, atherosclerosis and cardiovascular diseases. Recent studies have proven the anti-inflammatory properties of 1,4-dihydropyridines (1,4-DHPs) and its derivatives, which have many biological properties including calcium channel blockers. The structures of the synthesized compounds were elucidated by IR, 1H-NMR, 13C-NMR and HRMS methods. The cytotoxic properties of the compounds were determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method in 3T3 cell line. Among the 15 compounds, the three compounds …

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.

[3+2]-Cycloadditions Of Tertiary Amine N-Oxides And Dipolarophiles Providing An Efficient Route To Heterocyclics And 1,2-Diamines, And Nickel Catalayzed Transformations, Sarah Hejnosz

Electronic Theses and Dissertations

Nitrogen containing compounds are ubiquitous in nature as well as pharmaceuticals. These structures exhibit rich bioactive and chemical properties boasting an array of practical applications. As a result, the synthetic methods of forming nitrogen containing compounds are highly sought after. More efficient syntheses of these structures could result in less expensive industrial processes, particularly in the pharmaceutical industry. Roussi and coworkers established a highly efficient synthetic route forming nitrogen containing heterocycles in a single step from commercially available reagents, however this chemistry has not be used since its discovery in the 1980. Herein, this work greatly expanded Roussi’s method and …

Pyrrolopyrrole-Based Materials For High-Contrast Electrochromics, Allison Marie Hawks

Master of Science in Chemical Sciences Theses

Understanding structure-property relationships of underutilized p-conjugated chromophores is an important task for the continued discovery of materials that will find utility in organic electronic applications. Dihydropyrrolo[3,2-b]pyrroles (DHPPs) are synthetically simple and highly tailorable chromophores that can be decorated with diverse functionalities that readily manipulate optoelectronic properties useful for a variety of applications. However, a thorough understanding of how these functionalities influence properties of DHPPs that will be useful in applications such as electrochromism is unknown. Motivated to exploit the synthetic simplicity and tailorability of DHPPs, a family of DHPP chromophores was synthesized to probe how functionality and connectivity …

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 …

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 (ETD)

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 …

Applying Intensity-Based Methods To Disentangle Microwave Spectra Of Complex Mixtures: Analysis Of Weakly Bound Clusters Of 1,1-Difluoroethylene/Co2, Hannah Fino

Masters Theses

Microwave spectroscopy is used to study the solvent-solute interactions between molecules of CO₂ and fluoroethylenes by analyzing the formation of weakly-bound clusters in a gaseous mixture. One of the challenges to analyzing microwave spectra obtained for these weakly-bound species is that spectra for individual clusters are mixed together in an original complex spectrum. This prompts development of automated techniques that could separate complex data into subsets of related data to be more easily analyzed.

The techniques developed in this work are founded on intensity-based analyses, following the work of Dr. Robert Field on Extended Cross Correlation (XCC). The XCC …

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. …

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 And Cyclotrimerization Of Sulfonyl Enynes, Alexa C. Martin

Graduate Theses, Dissertations, and Problem Reports (ETD)

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 …

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 …

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 …

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, …

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. …

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 …

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.