Asymmetric Diel Reaction Lab Report
Equ 13. 4-(5-nolyl)-Pyridinum Cation Containing CILs Catalyzed Aldol Reactions Equ 14. Amide Functionalized Proline based CILs Organocatalyst for Aldol Reactions 3.4. Asymmetric Diels-Alder reaction. In 1997, Howarth and his group80 reported first, the asymmetric Diels-Alder reaction by using dialkylimidazolium salts (chiral and achiral) as efficient organocatalyst between crotonaldehyde or methacrolein and cyclopentadiene. The enentiomeric excess was less than 5% and no such diastereoselectivity were observed. Here enantiomeric excess did not depends upon the ionic liquids chirality, both chiral CILs and achiral CILs gave the near about same results. After that time researchers have been tried to design and synthesized Lewis acid based …show more content…
The anionic CIL N-methylimidazolium (R)-camphorsulfonate was employed in the reaction with methyl vinyl ketone (Equ 19). After Michael addition, N-(3ꞌ-oxobutyl)-N-methylimidazolium (R)-camphorsulfonate was obtained. Using heterogeneous catalyst Ru/C in the hydrogenation reaction of this imidazolium cation functionalized carbonyl group to produce corresponding asymmetric alcohol gave moderate yield and enantioselectivity 80% ee was …show more content…
Enantioselective hydrogenation of keto functionalized ionic liquid. The field of asymmetric hydrogenation reactions using metal complexes has been well developed. These complexes are generated from assymmtric chiral ligands such as atropoisomeric binaphthyls and biphenyls. In 2007, Francio and group88 reported asymmetric hydrogenation reaction catalyzed by tropoiosmeric ligand based rhodium complex in presence of amino acid based CIL 71 as a chiral solvent. In this reaction the chirality of hydrogenated product arises from CILs and enantioselectivities up to 69% ee were observed (Equ 20). In 2008, the same group89 reported hydrogenation reaction using transition metal complex with racemic ligands instead of enantiopure ligands in presence of CILs. The same results were observed by using both the racemic ligands and enantiomerically pure ligands (Equ 20). These results were observed mainly due to the chiral poisoning by the CILs in racemic 2,2ꞌ-bis(diphenylphosphanyl)-1,1ꞌ-binaphthyl ligands which was connecting with metals. Equ 20. Enantioselective hydrogenation in amino acid-based CILs. 3.6. Biginelli
Cis Conformation Lab Report
969 Words | 4 PagesFor this experiment, stereochemistry was observed by analyzing both the isomerization of dimethyl maleate and carvones. The dimethyl maleate is formed by two methyl ester groups that are connected by an alkene. They are in a cis-conformation meaning they are on the same side of the alkene, therefore the esters are close to one another. This conformation is strained and sterically hindered due to electrons repelling each other and are enantiomers of one another. With the use of radical chemistry, the cis conformation can be changed into a trans configuration where the esters are on opposite sides of one another.
Nucleophilic Substitution Reaction Lab Report
840 Words | 4 PagesIntroduction:- In organic chemistry the substitution reactions is the most important reactions, especially Nucleophilic aromatic substitution reactions where nucleophile attacks positive charge or partially positive charge As it does so, it replaces a weaker nucleophile which then becomes a leaving group. The remaining positive or partially positive atom becomes an electrophile. The general form of the reaction is: Nuc: + R-LG → R-Nuc + LG: The electron pair (:) from the nucleophile (Nuc :) attacks the substrate (R-LG) forming a new covalent bond Nuc-R-LG.
Maleic Anthracene Essay
525 Words | 3 PagesDiscussion In this experiment, anthracene and maleic anhydride were reacted in solution to produce a single organic product in crystal form. Anthracene is composed of a 3 carbon rings where the first ring has a 3 pi bonds while the other two has 2. Also, the double bonds are separated by single sigma bonds, which conjugate the double bond. Maleic anhydride has a five-membered ring with ring’s oxygen atoms bonded to two acyl group, ester R-COO.
5 Aminotetrazole Monohydrate Lab Report
912 Words | 4 PagesChloroacetic acid (0.5 g, 5. 28 mmol), 5-aminotetrazole monohydrate (0.45 g, 5. 28 mmol), and sodium hydroxide (0.59 g, 10.57 mmol) in 10 ml of water was refluxed 20 hr, cooled, and made strongly acidic with concentrated hydrochloric acid. The mixture was cooled overnight and precipitate was separated to give 0.28 g a white solid product at 45.41% yield. (5-Amino-tetrazol-1-yl)-acetic acid: Yield: 45.41%; white crystals; m.p 210-213°C; IR (KBr): 3388, 3315, 3270, 3205, 3010, 2976, 1697, 1638, 1586, 1496, 1257 cm-1; 13C NMR (75 MHz (DMSO-d6)): 168, 156,
Preparation Of L-Phenylalanine Lab Report
802 Words | 4 Pages“Diazotization of L-phenylalanine results in the unstable aliphatic diazonium salt 2, which is believed to undergo a rapid, intramolecular SN2 reaction to give the highly strained R-lactone (3) (3)”. “In a second, slower, intermolecular SN2 reaction, 3 reacts with the solvent (water) to open the lactone and yield the final product, (S)-2-hydroxy-3-phenylpropanoic acid (4)”. “Because this process occurs with two SN2 reactions, the final product has a net retention of configuration”. “This reaction has the added advantage of being environmentally friendly: the reaction is run in aqueous solution, using a safe amino acid and generates no hazardous waste requiring disposal”. “This experiment illustrates some important chemical concepts, including: Water solubility dependence on the state of ionization of a compound, Stereospecificity of the SN2 reaction, Measurement of optical activity, Effect of diastereotopic protons in the 1 H NMR spectrum”.
Cross Condensation Of Aldol Lab Report
838 Words | 4 PagesCross Condensation of aldol 2015007632 Dowrie, K Contents Reaction 1 Introduction 1 Experiment Procedure 2 Experimental results 3 Table of calculations 3 Calculations 3 NMR 4 TLC 4 References 5 Reaction Introduction An aldehyde reaction is when aldehydes and keytones, both containing an α-hydrogen in the presence of an alkali group condenses and forms an enone. Acetone has α-hydrogens on each side. The proton can be removed and therefore giving a nucleophile anion. The aldehyde carbonyl is more reactive than the keytone and so it reacts rapidly with the anion.
Methyl Trans-Cinnamate Lab Report
1399 Words | 6 PagesIt is understood the mechanism is acid-catalyzed where protons coordinate with the carbonyl oxygen to make the carbonyl carbon more electropositive for nucleophilic attack (Scheme 1). In the experimental procedure all reactants were added together, this is inefficient as the protons can coordinate with either trans-cinnamic acid or methanol. Coordination with methanol is unnecessary as it reduces its nucleophilicity and makes less protons available to coordinate with the carboxylic acid. To improve
How Can Cyclooctyne Effectively Reaction With A Vinylketene Complex
131 Words | 1 PagesThe major research question of my studies is if cyclooctyne can be successfully reacted with a vinylketene complex using a cost-effective methodology and in producing a distinct organic complex. In this experiment, a tricarbonyl iron(0) vinylketene complex was reacted with cyclooctyne in a cycloaddition reaction. The method used in this experimentation was based on the fundamentals of Click Chemistry. Since, reactions designed according to the concepts of Click Chemistry produced inoffensive byproducts and high yields, it was hypothesized that this reaction would produce a new methodology in how to synthesize cyclooctyne reacted complexes and produce an unknown organic complex. The primary goal in this research was to form an unknown* complex
Ester Synthesis Lab Report
250 Words | 1 PagesThe goal of this experiment was to synthesize the unknown ester through Fischer Esterification. This procedure involves treating a carboxylic acid with an alcohol and a strong acid catalyst. This procedure was also catalyzed with heat at 160oC-180oC, to keep the temperature from exceeding the boiling points of the compounds in use. The acid catalyst protonated the double bonded oxygen atom to force the atom to pull two electrons away from the double bond in order to stabilize the atom’s charge. As this electron shift occurred, the alcohol attacked the carbocation that lost its double bond.
Azirines Derivatives Research Paper
1467 Words | 6 PagesTherefore, the synthesis of new compounds has become an important goal for researchers in recent years. For this purpose, various compounds incorporating a azirine ring have been synthesized and biological activities have been reported. Recently, it has been reported that a considerable number of azirine derivatives bear different biological activities. Among these compounds, azirine derivatives show various biological
Ketones Lab Report
2072 Words | 9 Pages1. Introduction Friedel–Crafts acylation of aromatic compounds is one of the most important and practical methods to prepare aromatic ketones. The resulting diaryl ketones are important chemical intermediates for the synthesis of a wide range of compounds such as pharmaceuticals, fragrances, flavors, dyes and agrochemicals [1,2]. This is an electrophilic acylation of aromatic compounds with acid chlorides or acid anhydrides, which is traditionally catalyzed by Lewis acids, such as AlCl3, BF3, SbCl5, FeCl3, ZnCl2, SnCl4, TiCl4 or strong protonic acids, such as H2SO4, HF [3-7]. The major drawbacks of these catalysts are that they are hazardous, corrosive, non-recoverable and usually more than stoichiometric amounts of catalysts are required.
Ionic Analysis
1351 Words | 6 PagesFigure 1 shows the synthesized ionic liquid of CVD with studied acidic compounds (white crystalline materials) in 1:1 molar ratio after dissolving them in methanol and complete solvent evaporation after five days. CVD with CA, TA and SAC convert to a viscous yellow liquid form. This method was used to preparation of different ionic liquid form of drugs such as ketoconazole with TA and CA (24) and sulfasalazine and acyclovir with choline (28). ****Fig 1**** The DSC thermograms of CVD, CA, TA and their ionic liquid forms have been demonstrated in Figure 2.
9h2 Synthesis
804 Words | 4 PagesSynthesis of 2-[(4-methoxy-phenyl)iminomethyl]-4-nitrophenol (SB) The Schiff-base, 2-[(4-methoxy-phenyl)iminomethyl]-4-nitrophenol, (C14H12N2O4) was synthesized by using p-Anisidine in methanol
Oxazole Synthesis
1577 Words | 7 PagesNamely, we would be able to prepare compounds (3) as precursors for Cornforth rearrangement reaction from 2-aryloxazoles (2) which are obtained by cyclization of the corresponding glycine (1). Then compounds (3) would be transformed to compounds (4) by optimization of the reaction conditions. First, 2-aryl-5-methoxyoxazoles (2) were prepared by the method of Wipf’s protocol12) from methyl N-arylcarbonyl glycine methyl esters (1) in the presence of Et3N in DCE with PPh3 and I2 at room temperature for 19-24hr. This reaction proceeded in mild condition and afforded compound (2) in 80-97% yield by column chromatography (Table 1).
L-Proline Lab Report
1021 Words | 5 PagesCoordination of metal cations with L-proline can be achieved in many possible modes,3, 27 and we chose the three coordination patterns recommended by the work of Fleming
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