DOCSLIB.ORG

Synthesis of Cis-Norbornene-5,6-Endo-Dicarboxylic Anhydride

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Synthesis of Cis-Norbornene-5,6-Endo-Dicarboxylic Anhydride RIBAR DIELS-ALDER REACTION Diels-Alder Reaction: Synthesis of cis-Norbornene-5,6-endo-dicarboxylic anhydride Jessica Ribar – U14763216 TA: Boliang Dong Lab Partner: Zoë Jones CHM 2211.905 RIBAR DIELS-ALDER REACTION Introduction Diels-Alder reactions occur when a conjugate addition reaction of a conjugate diene connected to an alkene takes place. In other words, when a dienophile and a diene react with each other. This reaction then produces a cyclohexene. A simple example of a Diels-Alder reaction is the reaction between 1,3-butadiene and ethyne, which forms 1,4-cyclohexadiene. This example is shown below in figure 1. Figure 1: Mechanism of synthesis of 2-methyl-1-butene. The Diels-Alder reactions are stereospecific, meaning an alkene undergoes addition that forms two additional s bonds, either syn or anti addition. In Diels-Alder reactions, cis reactants give a cis product, and trans reactants get trans products. If both diene substituents obtain the same stereochemistry, then they end up on the same face. However, if they have different stereochemistry, they will end up on opposite sides of the product. [1] The mechanism of the synthesis of Diels-Alder in this experiment is shown below in figure 2. As shown, when cyclopentadiene reacts with maleic anhydride, the product we are trying to achieve may form while it may also form the exo version of that same compound. Figure 2: Mechanism of synthesis of cis-Norbornene-5,6-endo-dicarboxylic anhydride RIBAR DIELS-ALDER REACTION The possible side reaction for the Diels-Alder reaction is the formation of dicyclopentadiene. This reaction is shown in figure 3. Figure 3: Possible side reaction during the synthesis. Experimental Procedure Figure 3: Flow chart of experiment 2. Cracking dicyclopentadiene and performing the Diels-Alder reaction. [2] RIBAR DIELS-ALDER REACTION Chemical Tables Dicyclopentadiene Maleic Anhydride Ethyl Acetate Formula !"#$"% !&$%'( !&$)'% Molar Mass 132.206 g/mol 98.057g/mol 88.106 g/mol Structure Melting 10.31 ℃ 52.56 ℃ -83.8 ℃ Point Physical Colorless crystalline solid. Colorless or white crystals with Fruity odor with bittersweet Properties Sharp unpleasant odor. pungent odor. taste. Table 1: Physical and chemical properties of the main chemicals used for experiment 2. [3] Results Physical Appearance Mass Collected Percent Yield Melting Point White crystals. 0.257 g 76.7 % 140-145 ℃ Calculating Theoretical Mass " BCD EF Maleic Anhydride (MA) à 0.204> ?@× = 0.002 JKL ?@ G)." H EF 164.2 > VW MℎOKPOQRSTL ?TUU à 0.002 JKL VW× = 0.335 > VW 1 JKL VW Actual Mass Collected \RTL ]RQℎ ^PK_`SQ > − MTPO_ bRTL > = @JK`cQ Kd ^PK_`SQ (>) 26.02 g − 25.975 g = 0.045 g Amount collected: 0.212 g + 0.045 g = 0.257 g Calculating Percent Yield @SQ`TL JKLOU 0.257 > = h 100% = 76.7% MℎOKPOQRSTL JKLOU 0.335 > RIBAR DIELS-ALDER REACTION Discussion The amount of product obtained was converted into moles to achieve the percent yield which was 76.7 %. For this experiment, the percent yield accomplished was decent. The possible side reaction of cis-Norbornene-5,6- endo-dicarboxylic anhydride could have occurred to lower the percent yield. The simple distillation process performed was unable to produce the cyclopentadiene needed for the second part of the experiment. This problem was fixed by using product from another group’s distillation process. The melting point obtained from the sample collected was less than the literature value by about 20 ℃ which is a pretty significant amount. This could have resulted from a few different factors. The cyclopentadiene formed could have distilled for too long which could have affected the product for the Diels-Alder reaction. The amount of cyclopentadiene used for this experiment was also much higher than instructed to add. This could have skewed the results. Conclusion Diels-Alder reactions are used prevalently in the scientific community. David Staple and Samuel Butcher have used Diels-Alder reactions for their research in studying RNA structures with diverse functions. The information obtained about the RNA catalyzing the C-C bond that was formed from a Diels-Alder reactions led to discoveries about the RNA itself and how it conforms to a fold of its three helicases. [4] Overall, this experiment did not produce a Diels-Alder product. This can be stated because of the significant difference in the melting points of the sample obtained and the literature value. With a better simple distillation set up and careful measurements and observations, the experiment could be successful. References 1. “Chapter 10: Diels-Alder Reactions.” Chemistry at University of Calgary. N.p. n.d. Web. 31 Jan. 2017. 2. Weldegirma, Solomon. "Experiment 2: Acid-Base Extraction." Experimental Organic Chemistry 6 (2016): 10-11. 3. “Dicyclopentadiene, Maleic Anhydride, Ethyl Acetate CH3COOC2H5 – PubChem.” National Center for Biotechnology Information. U.S. National Library of Medicine, n.d. Web. 31 Jan. 2017. 4. Staple, David, and Samuel Butcher. “Pseudoknots: RNA Structures with Diverse Functions.” PLOS Biology. N.p,n.d. Web. 31 Jan. 2017. .
Load more

Recommended publications
  • Cyclohexane Oxidation Continues to Be a Challenge Ulf Schuchardt A,∗, Dilson Cardoso B, Ricardo Sercheli C, Ricardo Pereira A, Rosenira S
    Applied Catalysis A: General 211 (2001) 1–17 Review Cyclohexane oxidation continues to be a challenge Ulf Schuchardt a,∗, Dilson Cardoso b, Ricardo Sercheli c, Ricardo Pereira a, Rosenira S. da Cruz d, Mário C. Guerreiro e, Dalmo Mandelli f , Estevam V. Spinacé g, Emerson L. Pires a a Instituto de Qu´ımica, Universidade Estadual de Campinas, P.O. Box 6154, 13083-970 Campinas, SP, Brazil b Depto de Eng. Qu´ımica, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil c College of Chemistry, University of California, Berkeley, CA 94720, USA d Depto Ciências Exatas e Tecnológicas, Universidade Estadual de Santa Cruz, 45650-000 Ilhéus, BA, Brazil e Universidade Federal de Lavras, Lavras, MG, Brazil f Instituto de Ciências Biológicas e Qu´ımicas, PUC-Campinas, 13020-904 Campinas, SP, Brazil g Sup. Caracterização Qu´ımica, IPEN, 05508-900 São Paulo, SP, Brazil Received 3 October 2000; received in revised form 21 December 2000; accepted 28 December 2000 Abstract Many efforts have been made to develop new catalysts to oxidize cyclohexane under mild conditions. Herein, we review the most interesting systems for this process with different oxidants such as hydrogen peroxide, tert-butyl hydroperoxide and molecular oxygen. Using H2O2, Na-GeX has been shown to be a most stable and active catalyst. Mesoporous TS-1 and Ti-MCM-41 are also stable, but the use of other metals such as Cr, V, Fe and Mo leads to leaching of the metal. Homogeneous systems based on binuclear manganese(IV) complexes have also been shown to be interesting. When t-BuOOH is used, the active systems are those phthalocyanines based on Ru, Co and Cu and polyoxometalates of dinuclear ruthenium and palladium.
    [Show full text]
  • A Novel Series of Titanocene Dichloride Derivatives: Synthesis, Characterization and Assessment of Their
    A novel series of titanocene dichloride derivatives: synthesis, characterization and assessment of their cytotoxic properties by Gregory David Potter A thesis submitted to the Department of Chemistry in conformity with the requirements for the degree of Doctor of Philosophy Queen’s University Kingston, Ontario, Canada May, 2008 Copyright © Gregory David Potter, 2008 Abstract Although cis-PtCl2(NH3)2 (cisplatin) has been widely used as a chemotherapeutic agent, its use can be accompanied by toxic side effects and the development of drug resistance. Consequently, much research has been focused on the discovery of novel transition metal compounds which elicit elevated cytotoxicities coupled with reduced toxic side effects and non-cross resistance. Recently, research in this lab has focused on preparing derivatives of titanocene dichloride (TDC), a highly active chemotherapeutic agent, with pendant alkylammonium groups on one or both rings. Earlier results have demonstrated that derivatives containing either cyclic or chiral alkylammonium groups had increased cytotoxic activities. This research therefore investigated a new series of TDC complexes focusing specifically on derivatives bearing cyclic and chiral alkylammonium groups. A library of ten cyclic derivatives and six chiral derivatives were synthesized and fully characterized. These derivatives have undergone in vitro testing as anti-tumour agents using human lung, ovarian, and cervical carcinoma cell lines (A549, H209, H69, H69/CP, A2780, A2780/CP and HeLa). These standard cell lines represent solid tumour types for which new drugs are urgently needed. The potencies of all of the Ti (IV) derivatives varied greatly (range from 10.8 μM - >1000 μM), although some trends were observed. In general, the dicationic analogues exhibited greater potency than the corresponding monocationic derivatives.
    [Show full text]
  • Catalysis Science & Technology
    Catalysis Science & Technology Accepted Manuscript This is an Accepted Manuscript, which has been through the Royal Society of Chemistry peer review process and has been accepted for publication. Accepted Manuscripts are published online shortly after acceptance, before technical editing, formatting and proof reading. Using this free service, authors can make their results available to the community, in citable form, before we publish the edited article. We will replace this Accepted Manuscript with the edited and formatted Advance Article as soon as it is available. You can find more information about Accepted Manuscripts in the Information for Authors. Please note that technical editing may introduce minor changes to the text and/or graphics, which may alter content. The journal’s standard Terms & Conditions and the Ethical guidelines still apply. In no event shall the Royal Society of Chemistry be held responsible for any errors or omissions in this Accepted Manuscript or any consequences arising from the use of any information it contains. www.rsc.org/catalysis Page 1 of 6 CatalysisPlease doScience not adjust & Technology margins Journal Name ARTICLE Hydrophenylation of internal alkynes with boronic acids catalysed by a Ni-Zn hydroxy double salt-intercalated Received 00th January 20xx, Accepted 00th January 20xx Manuscript DOI: 10.1039/x0xx00000x anionic rhodium(III) complex www.rsc.org/ Takayoshi Hara, 1 Nozomi Fujita, 1 Nobuyuki Ichikuni, 1 Karen Wilson, 2 Adam F. Lee, 2 and Shogo Shimazu* 1 3- [Rh(OH) 6] intercalated Ni–Zn mixed basic salts (Rh/NiZn) are efficient catalysts for the hydrophenylation of internal alkynes with arylboronic acids under mild conditions.
    [Show full text]
  • Synthesis and Reactions of Ferrocene
    R Carbon Synthesis and Reactions of Ferrocene R Carbon Carbon Contents Objectives 1 Introduction 1 Preparation of ferrocene 2 Acetylation of ferrocene 7 Preparation of [Fe(η-C5H5)(η-C6H6)]PF6 10 Reaction of [Fe(η-C5H5)(η-C6H6)] PF6 with nucleophiles 12 Manuscript prepared by Dr. Almas I. Zayya, Dr. A. Jonathan Singh and Prof. John L. Spencer. School of Chemical and Physical Sciences, Victoria University of Wellington, New Zealand. R Carbon Objectives Introduction The principal aims of these experiments are to The archetypal organometallic compound provide experience in the synthesis, isolation, ferrocene, [Fe(η-C5H5)2], is of historical importance purification and characterisation of organometallic since its discovery and structural characterisation compounds. Purification techniques include in the early 1950s sparked extensive research into distillation, sublimation, chromatography and the chemistry of metal sandwich compounds.1 crystallisation. The main characterisation Two of the chemists who first proposed the correct technique used in these experiments is 1H NMR structure of ferrocene (Figure 1), Geoffrey Wilkinson spectroscopy using the benchtop Spinsolve and Ernst Otto Fischer, were awarded the Nobel spectrometer. Furthermore, students will Prize in Chemistry in 1973 for their pioneering work also develop their synthetic skills using inert on the chemistry of sandwich complexes. atmosphere techniques. Ferrocene is an example of a π-complex in which interactions between the d-orbitals of the Fe2+ metal centre with the π-orbitals of the two planar - cyclopentadienyl ligands (C5H5 ) form the metal-ligand bonds. Thus, all the carbon atoms in the cyclopentadienyl rings are bonded equally to the central Fe2+ ion. Ferrocene exhibits aromatic properties and is thermally very stable.
    [Show full text]
  • United States Patent Office Patented May 7, 1963
    3,088,959 United States Patent Office Patented May 7, 1963 1. 2 or grouping of carbon atoms which is present in cyclo 3,088,959 pentadiene. This grouping is illustrated as PROCESS OF MAKENG CYCLOPENTADEENY NECKEL, NTROSYL COMPOUNDS Robert D. Feltham, Joseph F. Anzenberger, azad Jonatian T. Carrie, Pittsburgh, Pa., assignors to The Interaa tional Nickel Company, Inc., New York, N.Y., a corpo ration of Delaware No Drawing. FiRed Sept. 1, 1960, Ser. No. 53,374 The substituent groups on the cyclopentadiene moiety 6 Clains. (C. 260-439) 0. indicated as R, R2, R3, R and R5 are any one or more The present invention relates to the production of of hydrogen atoms, halogen atoms and/or organic groups nickel compounds and, more particularly, to the produc such as aliphatic groups, aromatic groups, alicyclic groups, tion of nickel nitrosyl compounds containing a group etc. The substituent groups can also bond at two posi having the cyclopentadienyl moiety. tions. Where this occurs, groups can substitute for adja Compounds such as cyclopentadienylnickel nitrosyl, 5 cent R groups, e.g., Ra and R3 and/or R4 and R5 to form methylcyclopentadienylnickel nitrosyl and other complex indene and other condensed ring structures. nitrosyl compounds containing a cyclopentadienyl-type As mentioned hereinbefore, when carrying out the proc group have been made. Such compounds have use as ess of the present invention, the reactants are reacted in gasoline additives. When such use is contemplated, it is the presence of a base. The base can advantageously be economically imperative that the compounds be produced 20 a nitrogen base or a phosphorus base or an alkoxide of a in good yield from the most readily available and inex metal having a strong hydroxide.
    [Show full text]
  • Chem 267. Cyclohexene. (Revised 7/10). in This Experiment You Will
    Chem 267. Cyclohexene. (revised 7/10). In this experiment you will synthesize cyclohexene and purify it by distillation. You will check the purity and identity of the product by gas chromatography (GC) and infrared spectroscopy (IR). You will also do some simple chemical tests which distinguish alkenes from alkanes. Review the chapter on distillation and your notes from the distillation experiment. The "Things to Watch Out For in Distillations" listed for the distillation experiment are common to this distillation as well. As always, use care when inserting the thermometer into the thermometer adaptor. Hold the thermometer close to the adaptor and push and twist gently. Breakage could result in a serious injury. Check for frayed connectors and cracked flasks. Cyclohexene has a disagreeable odor, characteristic of volatile alkenes. Allow the apparatus to cool before disassembling it in the hood, and dispose of the wastes in the hood in the PROPER CONTAINERS (see below). Rinse the apparatus with a LITTLE acetone and dispose of that in the Nonhalogenated Liquid Waste container. CAUTION: cyclohexene is very flammable. Handle phosphoric acid with care. It is corrosive to tissue. If your skin comes into contact with phosphoric acid, wash the contaminated area immediately with water, then soap and water. Clean up spills immediately using the sodium bicarbonate in the hood. Do the Prelab Exercise on p. 334 (a model of a flow sheet is on p. 142). This is something to do for all synthesis experiments. Also always prepare a table of reactants and products such as that shown in the handout, “Sample Notebook and Report”.
    [Show full text]
  • Synthesis and Reactivity of Cyclopentadienyl Based Organometallic Compounds and Their Electrochemical and Biological Properties
    Synthesis and reactivity of cyclopentadienyl based organometallic compounds and their electrochemical and biological properties Sasmita Mishra Department of Chemistry National Institute of Technology Rourkela Synthesis and reactivity of cyclopentadienyl based organometallic compounds and their electrochemical and biological properties Dissertation submitted to the National Institute of Technology Rourkela In partial fulfillment of the requirements of the degree of Doctor of Philosophy in Chemistry by Sasmita Mishra (Roll Number: 511CY604) Under the supervision of Prof. Saurav Chatterjee February, 2017 Department of Chemistry National Institute of Technology Rourkela Department of Chemistry National Institute of Technology Rourkela Certificate of Examination Roll Number: 511CY604 Name: Sasmita Mishra Title of Dissertation: ''Synthesis and reactivity of cyclopentadienyl based organometallic compounds and their electrochemical and biological properties We the below signed, after checking the dissertation mentioned above and the official record book(s) of the student, hereby state our approval of the dissertation submitted in partial fulfillment of the requirements of the degree of Doctor of Philosophy in Chemistry at National Institute of Technology Rourkela. We are satisfied with the volume, quality, correctness, and originality of the work. --------------------------- Prof. Saurav Chatterjee Principal Supervisor --------------------------- --------------------------- Prof. A. Sahoo. Prof. G. Hota Member (DSC) Member (DSC) ---------------------------
    [Show full text]
  • Classification Tests for Hydrocarbons Using Solubility, Ignition, Nitration, Baeyer’S Test, Bromine Test and Basic Oxidation Test
    CLASSIFICATION TESTS FOR HYDROCARBONS USING SOLUBILITY, IGNITION, NITRATION, BAEYER’S TEST, BROMINE TEST AND BASIC OXIDATION TEST Jasher Christian Boado, Alyanna Cacas, Phoebe Calimag, Caryl Angelica Chin, Haidee Cosilet, John Francis Creencia Group 2, 2BMT, Faculty of Pharmacy, University of Santo Tomas ABSTRACT Hydrocarbons are classified as saturated, actively unsaturated, aromatic or an arene based on various classification tests involving test for solubility in concentrated H2SO4, ignition, active unsaturation using Baeyer’s test and Bromine test, aromaticity using nitration test, and basic oxidation test. This experiment aims to differentiate the intrinsic physical and the chemical properties of hydrocarbons, and to determine if it is saturated, actively unsaturated, aromatic or an arene. The sample compounds hexane, heptane, cyclohexane, cyclohexene, benzene and toluene were analyzed for their physical state in room temperature, color, and odor. Using solubility test, a drop of a sample was added cautiously into 1ml of concentrated H2SO4. Using the Baeyer’s Test and/or Bromine test in which 2 drops of 2% KmnO4 solution and 10 drops of 0.5% Br2 in CCl4 reagent, respectively, was added into 5 drops of a sample in a dry test tube, was shaken vigourously until the reagent is decolorized compared with water. Using Nitration test, 8 drops of nitrating mixture was added into 5 drops of a sample in a dry test tube, was observed for the formation of a yellow oily layer or droplet and was diluted with 20 drops of water. Using Basic Oxidation test, 8 drops of 2% KmnO4 solution and 3 drops of 10% NaOH solution was added into 4 drops of a sample in a dry test tube and was heated in a water bath for 2 minutes.
    [Show full text]
  • Efficient Production of Poly(Cyclohexene Carbonate)
    polymers Article Efficient Production of Poly(Cyclohexene Carbonate) via ROCOP of Cyclohexene Oxide and CO2 Mediated by NNO-Scorpionate Zinc Complexes Sonia Sobrino 1, Marta Navarro 2, Juan Fernández-Baeza 1, Luis F. Sánchez-Barba 2,* , Agustín Lara-Sánchez 1 , Andrés Garcés 2 , José A. Castro-Osma 1 and Ana M. Rodríguez 1 1 Centro de Innovación en Química Avanzada (ORFEO-CINQA), Departamento de Química Inorgánica, Orgánica y Bioquímica, Universidad de Castilla-La Mancha, Campus Universitario, 13071 Ciudad Real, Spain; [email protected] (S.S.); [email protected] (J.F.-B.); [email protected] (A.L.-S.); [email protected] (J.A.C.-O.); [email protected] (A.M.R.) 2 Departamento de Biología y Geología, Física y Química Inorgánica, Universidad Rey Juan Carlos, Móstoles, 28933 Madrid, Spain; [email protected] (M.N.); [email protected] (A.G.) * Correspondence: [email protected]; Tel.: +34-91-488-8504 Received: 4 September 2020; Accepted: 18 September 2020; Published: 21 September 2020 Abstract: New mono- and dinuclear chiral alkoxide/thioalkoxide NNO-scorpinate zinc complexes were easily synthesized in very high yields, and characterized by spectroscopic methods. X-ray diffraction analysis unambiguously confirmed the different nuclearity of the new complexes as well as the variety of coordination modes of the scorpionate ligands. Scorpionate zinc complexes 2, 4 and 6 were assessed as catalysts for polycarbonate production from epoxide and carbon dioxide with no need for a co-catalyst or activator under mild conditions. Interestingly, at 70 ◦C, 10 bar of CO2 pressure and 1 mol % of loading, the dinuclear thioaryloxide [Zn(bpzaepe)2{Zn(SAr)2}] (4) behaves as an efficient and selective one-component initiator for the synthesis of poly(cyclohexene carbonate) via ring-opening copolymerization of cyclohexene oxide (CHO) and CO2, affording polycarbonate materials with narrow dispersity values.
    [Show full text]
  • Chemistry 102 - Experiment 2
    Chemistry 102 - Experiment 2 http://www.miracosta.edu/home/dlr/102exp2.htm Experiment 2 Properties of Alkanes, Alkenes, Aromatic Compounds and an Alcohol In the reactions we will perform in this experiment, hexane will be used to represent the saturated hydrocarbons, cyclohexene will be used as an unsaturated hydrocarbon, and toluene, the aromatic hydrocarbon. Methanol will also be examined. You will use combustion, reactions with halogens and potassium permanganate, as well as solubility to characterize these organic compounds. As a precaution during these experiments, you should be extremely careful since hydrocarbons are extremely flammable. The Bunsen burner, or other sources of flames, will not be used in the laboratory, unless expressly directed by the instructor. The Bunsen burner, or other sources of flames, will not be used in the laboratory, unless expressly directed by the instructor (for the combustion part of this experiment, you will ignite your hydrocarbons using a match). All waste chemicals, both liquids or solids, will be disposed of in the appropriate waste containers. Methyl alcohol is not a hydrocarbon, since it contains the element oxygen, in addition to its carbon and hydrogen atoms. However, alcohols are used during many chemical processes, and like the hydrocarbons, can be used as a fuel. In fact Indy-type race cars (for the Indianapolis 500 race) often use methanol (a 1-carbon alcohol) as a fuel because it burns clean and is saver than conventional fuels because it does not burn as hot. After you do each part of this experiment, write conclusions that you can draw about each of the chemicals used.
    [Show full text]
  • Photooxidation of Cyclohexene in the Presence of SO2: SOA Yield and Chemical Composition Shijie Liu1,2,3, Long Jia2, Yongfu Xu2, Narcisse T
    Photooxidation of cyclohexene in the presence of SO2: SOA yield and chemical composition Shijie Liu1,2,3, Long Jia2, Yongfu Xu2, Narcisse T. Tsona1, Shuangshuang Ge2, Lin Du3,1,2 1Environment Research Institute, Shandong University, Jinan, 250100, China 5 2State Key Laboratory of Atmospheric Boundary Layer Physics and Atmospheric Chemistry, Institute of Atmospheric Physics, Chinese Academy of Sciences, Beijing, 100029, China 3Shenzhen Research Institute, Shandong University, Shenzhen, 518057, China Correspondence to: Lin Du ([email protected]); Yongfu Xu ([email protected]) Abstract. Secondary organic aerosol (SOA) formation from cyclohexene/NOx system with various SO2 concentrations 10 under UV light was investigated to study the effects of cyclic alkenes on the atmospheric environment in polluted urban areas. A clear decrease at first and then increase of the SOA yield was found with increasing SO2 concentrations. The lowest SOA yield was obtained when the initial SO2 concentration was in the range of 30-40 ppb, while higher SOA yield compared to that without SO2 could not be obtained until the initial SO2 concentration was higher than 85 ppb. The decreasing SOA yield might be due to the fact that the promoting effect of acid-catalyzed reactions on SOA formation was less important 15 than the inhibiting effect of decreasing OH concentration at low initial SO2 concentrations, caused by the competition reactions of OH with SO2 and cyclohexene. The competitive reaction was an important factor for SOA yield and it should not be neglected in photooxidation reactions. The composition of organic compounds in SOA was measured using several complementary techniques including Fourier transform infrared (FTIR) spectroscopy, ion chromatography (IC) and Exactive-Orbitrap mass spectrometer equipped with electro-spray interface (ESI).
    [Show full text]
  • United States Patent Office Patented Apr
    2,882,288 United States Patent Office Patented Apr. 14, 1959 1 2 ber and character of substituents on the cyclopentadienyl carbon ring may otherwise be varied at will. Suitable 2,882,288 organic compounds include hydrocarbon compounds hav ORGANOVANADIUM HALIDES AND PROCESS ing the requisite alicyclic cyclopentadienyl carbon ring. OF PREPARATION Examples of such hydrocarbon compounds are cyclo John C. Brantley and Edward L. Morehouse, Snyder, pentadiene, its aliphatic derivatives as for example methyl, N.Y., assignors to Union Carbide Corporation, a cor ethyl, allyl and vinyl cyclopentadiene, its aromatic deriv poration of New York atives as for example phenyl cyclopentadiene, indene and its comparable derivatives. No Drawing. Application September 23, 1953 10 The formation of a dihalide according to this invention Serial No. 381,968 may be illustrated by the reaction between cyclopenta 11 Claims. (C. 260-429) dienyl magnesium chloride and VCla. The Grignard re agent may be prepared by reacting magnesium turnings with a lower alkyl chloride in a solvent, ethyl ether, bein This invention relates to organo-metallic compounds zene or the like for example, and reacting the resulting containing vanadium as the metal component. The in solution with cyclopentadiene. The cyclopentadienyl vention includes correlated improvements and discoveries magnesium chloride thus formed is then reacted with whereby such vanadium compounds having distinctive VCl4 in a suitable liquid medium and the organo properties are obtained. vanadium dichloride (C5H5)VCl may be recovered An object of the invention is to provide organo-metallic 20 from the reaction mixture. The same compound results compounds containing vanadium as the metallic compo from reaction of cyclopentadienyl magnesium chloride nent linked to the organic component by carbon to metal with VOCl3.
    [Show full text]