Deuterium

Discovery and Applications in Organic Chemistry
 
 
Elsevier (Verlag)
  • 1. Auflage
  • |
  • erschienen am 15. Mai 2016
  • |
  • 130 Seiten
 
E-Book | ePUB mit Adobe DRM | Systemvoraussetzungen
978-0-12-811041-6 (ISBN)
 

Deuterium: Discovery and Applications in Organic Chemistry provides a well-illustrated overview of the discovery of 2H or Heavy Hydrogen, the stable hydrogen isotope with both a proton and a neutron in its nucleus. The work introduces the isotope, its discovery, physical properties, nomenclature, and common compounds. It explores its application in organic chemistry in detail, through classic and recent examples from literature. Finally, the book devotes one chapter to Deuterium in medicinal chemistry and, notably, the biological effects of Deuterium Oxide (D2O).


  • Unique coverage not found elsewhere; presented in an accessible, dedicated short work
  • Practical information and examples on the use of Deuterium (D or 2H, Heavy Hydrogen) in organic synthesis
  • Detailed description of Deuterium's discovery and applications in the pharmaceutical industry


Jaemoon Yang is Senior Chemist II at Cambridge Isotope Laboratories, Inc. in Andover, Massachusetts. He received his Ph.D. degree in organic chemistry in 2000 from the University of Pittsburgh under the supervision of Professor Craig Wilcox. He carried out his postdoctoral work with Professor Marisa Kozlowski at the University of Pennsylvania. He joined CIL in 2007 where he is actively involved in the synthesis of deuterium-labeled compounds and the development of better methods for efficient H/D exchange reactions. He has more than 10 publications in peer-reviewed journals from the graduate and postdoctoral research. He is the author of 'Six-Membered Transition States in Organic Synthesis" published in 2008.
  • Englisch
  • San Diego
  • |
  • USA
Elsevier Science
  • 9,09 MB
978-0-12-811041-6 (9780128110416)
0128110414 (0128110414)
weitere Ausgaben werden ermittelt
  • Front Cover
  • Deuterium
  • Copyright Page
  • Dedication
  • Contents
  • Acknowledgments
  • Introduction
  • Hydrogen Is Ubiquitous
  • Applications
  • No Single Book Is Found
  • References
  • 1 Isotopes
  • 1.1 Definition
  • 1.2 Isotopes of Hydrogen
  • 1.3 Uses of Deuterium in Organic Chemistry
  • References
  • 2 Deuterium
  • 2.1 Discovery
  • 2.1.1 Atomic Weights of Protium and Deuterium
  • 2.1.2 Deuteron Versus Deuton
  • 2.2 Deuterium Gas (D2)
  • 2.3 Deuterium Oxide (D2O)
  • 2.3.1 Current Way of Producing Heavy Water
  • References
  • 3 Deuterium-Labeled Compounds
  • 3.1 Nomenclature
  • 3.1.1 Isotopologues and Isotopomers
  • 3.1.2 Isotopic Steroisomers
  • 3.2 Synthesis of Organic Compounds
  • 3.2.1 Benzene-d6
  • 3.2.2 Mechanism of Pt-Catalyzed H/D Exchange Reaction
  • 3.2.3 Acetone-d6 and Other Ketones
  • 3.2.4 Mechanism of Base-Catalyzed H/D Exchange Reaction
  • 3.2.5 DMSO-d6
  • 3.2.6 Chloroform-d (CDCl3)
  • 3.3 LiAlD4 and NaBD4
  • References
  • 4 Applications in Organic Chemistry
  • 4.1 Background
  • 4.1.1 Kinetic Isotope Effect
  • 4.1.2 Deuterium Tracer Study
  • 4.2 Classic Examples
  • 4.2.1 Reaction #1: Bromination of Acetone
  • 4.2.2 Reaction #2: Jones Oxidation
  • 4.2.3 Reaction #3: E2 Elimination
  • 4.2.4 Reaction #4: Reduction of Alkyl Halides by LiEt3BH
  • 4.2.5 Reaction #5: Hydroboration of Alkenes
  • 4.2.6 Reaction #6: Reaction of cis-Cyclodecene Oxide with Lithium Diethylamide
  • 4.2.7 Reaction #7: Hofmann-Löffler Reaction
  • 4.2.8 Reaction #8: Diels-Alder Reaction
  • 4.2.9 Reaction #9: Tishchenko Reduction
  • 4.2.10 Reaction #10: Asymmetric Isomerization of Allylamines to Enamines
  • 4.3 Recent Examples
  • 4.3.1 Reaction #11: Ruthenium-Catalyzed Coupling of Propargylic Ethers with Alcohols
  • 4.3.2 Reaction #12: Cobalt-Catalyzed (Z)-Selective Hydroboration of Terminal Alkynes
  • 4.3.3 Reaction #13: Palladium-Catalyzed C-H Activation of Alkyl Arenes
  • 4.3.4 Reaction #14: Reaction of Cyclohexanol with o-Benzynes
  • 4.3.5 Reaction #15: Palladium-Catalyzed Fluorination of Aryl Triflates
  • 4.3.6 Reaction #16: Ni-Catalyzed Coupling of N-Tosylaziridines with Alkylzinc Bromides
  • 4.3.7 Reaction #17: Reaction of Arylboronic Acids with Alkenyl Alcohols
  • 4.3.8 Reaction #18: Iodination of Resorcinol
  • 4.3.9 Reaction #19: Iridium-Catalyzed Asymmetric Hydroheteroarylation of Norbornene
  • 4.3.10 Reaction #20: Copper(I)/TEMPO-Catalyzed Aerobic Oxidation of Alcohols
  • 4.3.11 Reaction #21: Total Synthesis of N-Methylwelwitindoline C Isonitrile
  • 4.3.12 Reaction #22: Total Synthesis of Norzoanthamine
  • 4.3.13 Reaction #23: Scandium-Catalyzed C-H Functionalization
  • 4.3.14 Reaction #24: Meinwald Rearrangement Involving 1,2-Boryl Migration
  • 4.3.15 Reaction #25: Ring-Closing Metathesis-the Case of Nonproductive Events
  • 4.3.16 Reaction #26: Rearrangement of (Z)-Allylic Trichloroacetimidates to Allylic Esters
  • 4.3.17 Reaction #27: Ruthenium-Catalyzed Redox Isomerization of Propargylic Alcohols
  • 4.3.18 Reaction #28: Aldol Reactions of Methyl Ketone Lithium Enolates
  • References
  • 5 Applications in Medicinal Chemistry
  • 5.1 Biological Effects of D2O
  • 5.1.1 Can We Drink Heavy Water?
  • 5.2 Deuterium in Medicinal Chemistry
  • 5.2.1 Metabolism Studies
  • 5.2.2 Recent Progress in the Development of Deuterated Drugs
  • 5.2.2.1 Example 1: DeuteRx
  • 5.2.2.2 Example 2: Concert Pharmaceuticals
  • References
  • Conclusion
  • References
  • Author Index
  • Back Cover

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