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Organic Chemistry
Wisebridge Learning Systems Organic Chemistry Reaction Mechanisms Pocket-Book WLS www.wisebridgelearning.com © 2006 J S Wetzel LEARNING STRATEGIES CONTENTS ● The key to building intuition is to develop the habit ALKANES of asking how each particular mechanism reflects Thermal Cracking - Pyrolysis . 1 general principles. Look for the concepts behind Combustion . 1 the chemistry to make organic chemistry more co- Free Radical Halogenation. 2 herent and rewarding. ALKENES Electrophilic Addition of HX to Alkenes . 3 ● Acid Catalyzed Hydration of Alkenes . 4 Exothermic reactions tend to follow pathways Electrophilic Addition of Halogens to Alkenes . 5 where like charges can separate or where un- Halohydrin Formation . 6 like charges can come together. When reading Free Radical Addition of HX to Alkenes . 7 organic chemistry mechanisms, keep the elec- Catalytic Hydrogenation of Alkenes. 8 tronegativities of the elements and their valence Oxidation of Alkenes to Vicinal Diols. 9 electron configurations always in your mind. Try Oxidative Cleavage of Alkenes . 10 to nterpret electron movement in terms of energy Ozonolysis of Alkenes . 10 Allylic Halogenation . 11 to make the reactions easier to understand and Oxymercuration-Demercuration . 13 remember. Hydroboration of Alkenes . 14 ALKYNES ● For MCAT preparation, pay special attention to Electrophilic Addition of HX to Alkynes . 15 Hydration of Alkynes. 15 reactions where the product hinges on regio- Free Radical Addition of HX to Alkynes . 16 and stereo-selectivity and reactions involving Electrophilic Halogenation of Alkynes. 16 resonant intermediates, which are special favor- Hydroboration of Alkynes . 17 ites of the test-writers. Catalytic Hydrogenation of Alkynes. 17 Reduction of Alkynes with Alkali Metal/Ammonia . 18 Formation and Use of Acetylide Anion Nucleophiles . -
United States Patent (19) 11) 4,128,586 Ratcliffe 45) Dec
United States Patent (19) 11) 4,128,586 Ratcliffe 45) Dec. 5, 1978 (54) CATALYTICREDUCTION OF AROMATIC 2,792,422 5/1957 Harris et al...................... 260/609 D SULFONYL HALDES WITH HYDROGEN 2,820,780 1/1958 Gutcho et al. ....................... 260/12 SULFDE TO YELD AROMATIC THOLS 2,986,581 5/1961 Levy et al. ........................... 260/608 3,994,980 1 1/1976 Kubicek .......................... 260/609 D. (75) Inventor: Charles T. Ratcliffe, Morristown, N.J. FOREIGN PATENT DOCUMENTS (73) Assignee: Allied Chemical Corporation, Morris 461101 4/1975 U.S.S.R.............................. 260/609 D Township, Morris County, N.J. Primary Examiner-Lewis Gotts Appl. No.: 881,952 Assistant Examiner-Molly C. Eakin 21 Attorney, Agent, or Firm-Horst M. Kasper 22) Filed: Feb. 27, 1978 (57) ABSTRACT 51 Int. Cl’............................................ CO7C 149/28 52) U.S. C. ................. 260/609 D; 260/302 S; A process for reducing aromatic sulfonyl halides with 260/302 F, 260/308 R; 260/608; 544/315; hydrogen sulfide. Hydrogen sulfide is contacted with 544/408; 548/337; 548/346; 546/290; 546/179; sulfonyl halides preferably in the presence of a solvent 54.6/139 and of a catalyst. The reaction forms thiols and pro 58) Field of Search ............. 260/609 D, 608, 294.8 R ceeds in the range of between about 50' and 300' C. There is little formation of disulfide and no cleavage of 56) References Cited the thiol group. U.S. PATENT DOCUMENTS 2,402,641 6/1946 Lazler et al. ......................... 260/609 20 Claims, No Drawings 4,128,586 1. -
"Fluorine Compounds, Organic," In: Ullmann's Encyclopedia Of
Article No : a11_349 Fluorine Compounds, Organic GU¨ NTER SIEGEMUND, Hoechst Aktiengesellschaft, Frankfurt, Federal Republic of Germany WERNER SCHWERTFEGER, Hoechst Aktiengesellschaft, Frankfurt, Federal Republic of Germany ANDREW FEIRING, E. I. DuPont de Nemours & Co., Wilmington, Delaware, United States BRUCE SMART, E. I. DuPont de Nemours & Co., Wilmington, Delaware, United States FRED BEHR, Minnesota Mining and Manufacturing Company, St. Paul, Minnesota, United States HERWARD VOGEL, Minnesota Mining and Manufacturing Company, St. Paul, Minnesota, United States BLAINE MCKUSICK, E. I. DuPont de Nemours & Co., Wilmington, Delaware, United States 1. Introduction....................... 444 8. Fluorinated Carboxylic Acids and 2. Production Processes ................ 445 Fluorinated Alkanesulfonic Acids ...... 470 2.1. Substitution of Hydrogen............. 445 8.1. Fluorinated Carboxylic Acids ......... 470 2.2. Halogen – Fluorine Exchange ......... 446 8.1.1. Fluorinated Acetic Acids .............. 470 2.3. Synthesis from Fluorinated Synthons ... 447 8.1.2. Long-Chain Perfluorocarboxylic Acids .... 470 2.4. Addition of Hydrogen Fluoride to 8.1.3. Fluorinated Dicarboxylic Acids ......... 472 Unsaturated Bonds ................. 447 8.1.4. Tetrafluoroethylene – Perfluorovinyl Ether 2.5. Miscellaneous Methods .............. 447 Copolymers with Carboxylic Acid Groups . 472 2.6. Purification and Analysis ............. 447 8.2. Fluorinated Alkanesulfonic Acids ...... 472 3. Fluorinated Alkanes................. 448 8.2.1. Perfluoroalkanesulfonic Acids -
Process for the Preparation of Substituted N-\Aryl
Europaisches Patentamt European Patent Office © Publication number: 0 537 611 A1 Office europeen des brevets EUROPEAN PATENT APPLICATION © Application number: 92117123.7 int. Ci.5; C07D 487/04, A01 N 43/90, //(C07D487/04,249:00,239:00) @ Date of filing: 07.10.92 © Priority: 08.10.91 US 772990 © Applicant: DOWELANCO 9002 Purdue Road @ Date of publication of application: Indianapolis, Indiana 46268-1 189(US) 21.04.93 Bulletin 93/16 @ Inventor: Johnson, Timothy C. © Designated Contracting States: 1047 Orange Street AT BE CH DE DK ES FR GB IT LI NL Concord, California 9451 8(US) Inventor: Nasutavicus, Wilmonte A. 1700 Reliez Valley Road Lafayette, California 94549(US) © Representative: Huber, Bernhard, Dipl.-Chem. et al Patentanwalte H. Weickmann, Dr. K. Fincke F.A. Weickmann, B. Huber Dr. H. Liska, Dr. J. Prechtel Kopernikusstrasse 9 Postfach 86 08 20 W-8000 Munchen 86 (DE) © Process for the preparation of substituted N-(aryl)-1,2,4-triazolopyrimidine-2-sulfonamides. © The preparation of N-(aryl)-1 ,2,4-triazolopyrimidine-2-sulfonamides of formula (V) by the coupling of substi- tuted 1 ,2,4-triazolopyrimidine-2-sulfonyl halides of formula (VI) with aryl amines of substantially reduced nucleophilic reactivity is facilitated by conducting the reaction in the presence of a pyridine base and a catalytic amount of dimethyl sulfoxide. CO 00 Rank Xerox (UK) Business Services (3. 10/3.5x/3.0. 1) EP 0 537 61 1 A1 EP 0 537 61 1 A1 The present invention concerns a process for the preparation of N-(aryl)-1 ,2,4-triazolopyrimidine-2- sulfonamides by the coupling of aryl amines with substituted 1 ,2,4-triazolopyrimidine-2-sulfonyl halides. -
United States Patent Office
Patented Dec. 23, 1947 2432,991 UNITED STATES PATENT OFFICE ACYLATION OF THOPHENE Howard D. Hartough, Pitman, and John J. Sar della, Woodbury, N. J., assigners to Socony Wacuum Oil Company, incorporated, a corpo ration of New York No Drawing. Application January 8, 1946, Seria No. 642.13 12 Claims, (C. 260-329) 2 This invention relates to a catalytic acylation in carbon disulfide to a suspension of aluminum process for thiophenes and, more particularly, is chloride in the same solvent. If, however, a car directed to a method for acylating thiophene and oon disulfide solution of the acid chloride was its derivatives in the presence of glauconite as a added to a suspension of thiophene and alumi catalyst. r nun chloride, much tar was formed and a low The acylation of thiophene. and thiophene de yield of ketone resulted. The acylation of thio rivatives has previously been carried out employ phene has, accordingly, been an exceedingly dif ing Organic acid anhydrides, acyl halides, and fictly reaction to carry out, the usual acylation acyl nitriles as acylating agents and in the pres catalysts causing excessive resinification of the eace of various catalysts, including aluminun thiophene reactant. The resinification usually chloride, stannic chloride, titanium tetrachloride, occurs before acylation can be effected, and if phosphorus pentoxide and 2-chloronercurithio 'the expected reaction product is formed, it is phene. Other methodis of inaking acylated thio generally only in relatively Small amounts. phene include the dry distillation of calcium It has now been discovered that acylated thio salts of thiophene carboxylic acids and the action s phenes may be obtained in an efficient manner of nitriles on thienyiragnesium iodide. -
Synthesis and Characterization of Functionalized Poly(Arylene Ether Sulfone)S Using Click Chemistry
Wright State University CORE Scholar Browse all Theses and Dissertations Theses and Dissertations 2016 Synthesis and Characterization of Functionalized Poly(arylene ether sulfone)s using Click Chemistry Kavitha Neithikunta Wright State University Follow this and additional works at: https://corescholar.libraries.wright.edu/etd_all Part of the Chemistry Commons Repository Citation Neithikunta, Kavitha, "Synthesis and Characterization of Functionalized Poly(arylene ether sulfone)s using Click Chemistry" (2016). Browse all Theses and Dissertations. 1650. https://corescholar.libraries.wright.edu/etd_all/1650 This Thesis is brought to you for free and open access by the Theses and Dissertations at CORE Scholar. It has been accepted for inclusion in Browse all Theses and Dissertations by an authorized administrator of CORE Scholar. For more information, please contact [email protected]. SYNTHESIS AND CHARACTERIZATION OF FUNCTIONALIZED POLY (ARYLENE ETHER SULFONE)S USING CLICK CHEMSITRY A thesis submitted in partial fulfilment of the requirements for the degree of Master of Science By Kavitha Neithikunta B.sc Osmania University, 2010 2016 Wright State University WRIGHT STATE UNIVERSITY GRADUATE SCHOOL August 26, 2016 I HEREBY RECOMMEND THAT THE THESIS PREPARED UNDER MYSUPERVISION BY Kavitha Neithikunta ENTITLED Synthesis and Characterization of Functionalized Poly(arylene ether sulfone)s using Click chemistry BE ACCEPTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF Master of Science __________________________ Eric Fossum, Ph.D. Thesis Advisor ___________________________ David Grossie, Ph.D. Chair, Department of Chemistry Committee on Final Examination ____________________________ Eric Fossum, Ph.D. _____________________________ Daniel M. Ketcha, Ph.D. _____________________________ William A. Feld, Ph.D. _______________________________ Robert E. W. Fyffe, Ph.D Vice President for Research and Dean of the Graduate School ABSTRACT Neithikunta, Kavitha M.S., Department of Chemistry, Wright State University, 2016. -
Development of Nucleophile Assisting Leaving Groups (Nalgs)
DEVELOPMENT OF NUCLEOPHILE ASSISTING LEAVING GROUPS (NALGS) AND NEW STEREOSELECTIVE REACTIONS USING TITANIUM(IV) REAGENTS by Deboprosad Mondal A Dissertation Submitted to the Faculty of The Charles E. Schmidt College of Science in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy Florida Atlantic University Boca Raton, Florida December 2010 ACKNOWLEDGEMENTS I would like to thank my advisor, Dr. Salvatore D. Lepore, for his excellent guidance throughout my PhD. Dr. Lepore has opened for me a door to the art and science of chemical synthesis and methodology development. His talent, passion and motivation in synthesis and his kind personality have always inspired me to improve myself; I am grateful for his encouragement, patience and financial support. I want to thank my committee professors Predrag Cudic, Stanislaw Wnuk and Guodong Sui for their time and insightful advice on my research. I would also like to express my gratitude towards all the past and current members of the Lepore Research Group, especially Change He, Pradip, Ravi and Songye for their help and friendship throughout my PhD. Finally, I thank Drs. Anjan Bhunia and Maximilian Silvestri for their guidance during first year of my PhD. Now I wish to express my thanks to all my friends who have continually inspired me. I am deeply indebted to my parents, especially my father who was my ‘Guru’, my inspiration; my dada for his affection and love; maa-bapi, bhai, kaka for their unconditional love, support and inspiration. Finally, my wife Pinki, I am really proud of her for her love, inspiration and support. -
Process for Polymerizing Acrylonitrile
HH HI H HH I H HI H HI H HI II HI H HI II HI II HI H HI II HI HI H H HI I HI European Patent Office Office europeen des brevets EP 0 872 493 A2 EUROPEAN PATENT APPLICATION (43) Date of publication: (51) |nt CI.6: C08F 20/44 21.10.1998 Bulletin 1998/43 (21) Application number: 98302755.8 (22) Date of filing: 08.04.1998 (84) Designated Contracting States: (72) Inventor: Percec, Virgil AT BE CH CY DE DK ES Fl FR GB GR IE IT LI LU Chagrin Falls, Ohio 44022 (US) MC NL PT SE Designated Extension States: (74) Representative: Hoey, Shona AL LT LV MK RO SI BP International Limited Patents and Agreements Division (30) Priority: 14.04.1997 US 843259 Chertsey Road Sunbury-on-Thames, Middlesex TW16 7LN (GB) (71) Applicant: Case Western Reserve University Cleveland, Ohio 44106 (US) (54) Process for polymerizing acrylonitrile (57) This invention relates to a process for polymer- substituted halopropionitriles in the form of monoad- ising acrylonitrile, comprising: (A) forming a polymeris- ducts derived from sulfonyl halides and acrylonitrile, or able mixture comprising acrylonitrile monomer, solvent monoadducts derived from substituted sulfonyl halides and a metal catalyst; (B) contacting said mixture with an and monomers other than acrylonitrile; and (C) polymer- initiator, said initiator being selected from the group con- ising said acrylonitrile monomer to form a polymer com- sisting of sulfonyl halides, halopropionitriles, substituted prised of acrylonitrile. In one embodiment, the polymer- halopropionitriles in the form of monoadducts derived isable mixture in step (A) further comprises at least one from sulfonyl halides and acrylonitrile, monoadducts de- polymerisable comonomer other than acrylonitrile, and rived from substituted sulfonyl halides and monomers the polymer formed during step (C) is a copolymer or a other than acrylonitrile; or polymers containing end multicomponent copolymer comprised of acrylonitrile groups derived from sulfonyl halides, halopropionitriles, and said at least one other polymerisable comonomer. -
C:\Documents and Settings\Steve Murov\My
125 Exercise 15 - Preparation of a Key for Reaction-Map of Organic Chemistry (see Appendix C in student manual) Abstract: The Reaction -Map of Organic Chemistry has been designed to give organic chemistry students an overview of most of the reactions needed for the organic chemistry course. The chart has been partially organized according to the periodic table on the horizontal axis and according to carbon oxidation level on the vertical axis. In addition the carboxyls are grouped vertically according to decreasing reactivity and carbon - carbon bond forming reactions are emphasized with bold arrows. The chart provides a study aide for students and should help students develop synthetic routes from one functional group to another. The chart should be especially useful for students studying for the final examination for the two semester organic chemistry course. In addition to the chart, three keys are available that organize the reactions according to mechanism, functional group preparations and functional group reactions. Chemistry can be thought of a search for order in matter and this chart attempts to provide some insight into the order that exists in organic chemistry. Please note, “Supporting information reprinted with permission from J. Chem. Ed. 2007, 84(7), 1224. Copyright 2007 American Chemical Society.” Reaction-Map as a Study Aid At the end of a two semester course in organic chemistry, a student should be able to perform the exercises below. (Note: In addition to the exercises below, a student of organic chemistry should be able to demonstrate competency with spectroscopic, stereochemical and multistep synthetic challenges.) By performing the exercises below should result in the preparation of three keys for the Reaction-Map of Organic Chemistry. -
Diblock Copolymers Via Atom Transfer Radical Polymerization Utilizing Halide Exchange Technique
Polymer Journal, Vol. 37, No. 2, pp. 102–108 (2005) Synthesis of Amphiphilic Poly(ethylene oxide)-b-Poly(methyl methacrylate) Diblock Copolymers via Atom Transfer Radical Polymerization Utilizing Halide Exchange Technique y Xiaoyi SUN,1 Hailiang ZHANG,1; Lingjun ZHANG,1 Xiayu WANG,1 and Qi-Feng ZHOU2 1Institute of Polymer Science, Xiangtan University, Xiangtan 411105, Hunan Province, China 2Department of Polymer Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China (Received September 14, 2004; Accepted November 17, 2004; Published February 15, 2005) ABSTRACT: Amphiphilic diblock copolymers with different molecular weights and low polydispersities were synthesized by atom transfer radical polymerization (ATRP) of methyl methacrylate (MMA) using PEO–Br as an ini- tiator, which was obtained by the esterification of poly(ethylene oxide) (PEO) with 2-bromoisobutyryl bromide. The polymerization proceeded in solution using halide exchange technique to control ATRP. Fourier transform infrared spectroscopy (FT-IR) and 1H NMR studies confirm the composition of PEO–Br macroinitiator and related diblock co- polymers. The results obtained by GPC analysis show that the number average molecular weight was increased versus monomer conversion and the polydispersities were quite low (<1:10), which is the character of a controlled/‘‘living’’ polymerization. Moreover, the crystallization behavior of PEO-b-PMMA block copolymers was studied by means of differential scanning calorimetry (DSC). It was found -
Polyfluoroarenesulfonyl Chlorides Are Usually Obtained by Reactions Of
1 TRANSFORMATIONS OF POLYFLUOROARENESULFONYL HALIDES WITH ALKENES, POLYFLUOROARENETHIOLS AND ALKALI METAL HALIDES * Roman A. Bredikhin , Alexander M. Maksimov and Vyacheslav E. Platonov N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of Russian Academy of Sciences 630090, Academician Lavrentev Ave., 9, Novosibirsk, Russian Federation E-mail: [email protected] Abstract: The reactions of polyfluoroarenesulfonyl chlorides or bromides with polyfluoroarenethiols gave mixtures of polyfluorinated diaryl disulfides, whereas replacement of fluorine atom at the 4-position of aromatic ring of C6F5SO2F occured. The reactions of polyfluoroarenesulfonyl chlorides or bromides with some n-nucleophiles such as alkali metal halides probably proceed with electron transfer. The reactions of polyfluoroarenesulfonyl bromides with alkenes such as hexene-1 or allyl chloride provided the corresponding adducts in high yields, while the conversion of polyfluoroarenesulfonyl chlorides at the same conditions was poor and C6F5SO2F was unreactive. The reaction of polyfluoroarenesulfonyl bromides with allyl bromide resulted in allyl polyfluoroaryl sulfones. The formation of the products in reactions of polyfluoroareneslfonyl bromdes with alkenes apparently occurs with participation of polyfluoroarenesulfonyl radicals. Keywords: polyfluoroaromatic compounds, sulfonyl bromide, sulfonyl chloride, alkenes, radical addition, allyl polyfluoroaryl sulfone, thiols, metal halides, electron transfer, diaryl disulfide INTRODUCTION Non-fluorinated -
A Process for Preparing an Acyl Halide Or Sulfonyl Halide
~™ llll III II II III II III I II II III (19) J European Patent Office Office europeen des brevets (1 1 ) EP0 751 131 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int. CI.6: C07D 233/18, C07C 51/60, 02.01.1997 Bulletin 1997/01 C07C 303/02, C07B 41/1 0 (21) Application number: 96108936.4 (22) Date of filing: 04.06.1996 (84) Designated Contracting States: • Hayashi, Hidetoshi DE FR IT NL Ohmuta-shi, Fukuoka-ken, 836 (JP) • Mizuta, Hideki (30) Priority: 20.06.1995 JP 152826/95 Ohmuta-shi, Fukuoka-ken, 837 (JP) (71) Applicant: MITSUI TOATSU CHEMICALS, Inc. (74) Representative: Strehl Schubel-Hopf Groening & Chiyoda-Ku Tokyo 1 00 (JP) Partner Maximilianstrasse 54 (72) Inventors: 80538 Munchen (DE) • Nagata, Teruyuki Ohmuta-shi, Fukuoka-ken, 836 (JP) (54) A process for preparing an acyl halide or sulfonyl halide (57) A preparation process of acyl halide or sulfonyl halide which comprises reacting corresponding carboxylic acid or sulfonic acid with a haloiminium salt represented by the general formula (1): R'-N -R2 X ( 1 ) XCrU/n wherein R1 and R2 are same or different lower alkyl groups, X is a halogen atom, and n is an integer of 2 or 3. CO LO o Q_ LU Printed by Rank Xerox (UK) Business Services 2.13.10/3.4 EP0 751 131 A1 Description 1 . Field of the Invention 5 The present invention relates to a preparation process of acyl halide or sulfonyl halide. 2. Description of the Related Art In recent years, acyl halide has become important in industry as an intermediate for preparing heat resistant resin, 10 medicines and agricultural chemicals.