Deuterium: Discovery and Applications in Organic Chemistry

Description

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, also exploring its application in organic chemistry through classic and recent examples from literature. Finally, the book devotes one chapter to Deuterium in medicinal chemistry and the biological effects of Deuterium Oxide, better known as D2O. Deuterium Copyright Dedication 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 2.3 Deuterium Oxide 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 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 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 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 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