
The Organic Chemistry of Isotopic Labelling
by Hanson, James R.Buy New
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Summary
Table of Contents
An Introduction to the Organic Chemistry of Isotopic Labelling | p. xiii |
The Discovery and Detection of Isotopes | p. 1 |
Introduction | p. 1 |
The Discovery of Isotopes | p. 2 |
Early Applications of Isotopically Labelled Compounds | p. 5 |
The Selection of an Isotopic Label | p. 9 |
The Detection oflsotopes | p. 13 |
Nomenclature | p. 18 |
Labelling Compounds with Carbon-13 and Carbon-14 | p. 20 |
Introduction | p. 20 |
Carbon Labelling Using the Cyanide Jon | p. 21 |
Organometallic Reagents in Carbon Labelling | p. 24 |
The Wittig Reaction in Carbon Labelling | p. 27 |
Carbonyl Condensation Reactions in Carbon Labelling | p. 28 |
The Synthesis of Carbon-labelled Mevalonic Acid | p. 31 |
Aromatic Compounds Labelled in the Ring | p. 33 |
Ring-labelled Heterocyclic Compounds | p. 35 |
Biosynthetic Methods of Carbon Labelling | p. 38 |
Labelling with Deuterium and Tritium | p. 40 |
Introduction | p. 40 |
The Kinetic Isotope Effect | p. 41 |
The Isolation of Deuterium and Tritium | p. 42 |
Exchange Reactions in Deuterium and Tritium Labelling | p. 43 |
Heteroatom X-H Exchange Reactions | p. 44 |
General C-H Exchange Reactions | p. 44 |
Site-specific C-H Exchange Reactions | p. 45 |
Exchange Reactions of Carbonyl Compounds | p. 49 |
Exchange Reactions in the Preparation of Some Deuteriated Solvents | p. 51 |
Decarboxylation Reactions in Deuterium and TritiumLabelling | p. 51 |
Reduction Reactions | p. 52 |
Reducing Agents | p. 52 |
The Reduction of Carbonyl Groups | p. 54 |
The Hydrogenolysis of Aliphatic Substituents | p. 54 |
The Catalytic Reduction of Alkenes and Alkynes | p. 54 |
The Hydrogenolysis of Aryl Halides | p. 56 |
The Reduction of Iminium Salts | p. 58 |
The Hydrogenolysis of Organometallic Compounds | p. 58 |
Hydroboration | p. 59 |
Deuterium- and Tritium-labelled Alkyl Halides | p. 60 |
Stereochemical Aspects of Labelling with Hydrogen Isotopes | p. 62 |
Introduction | p. 62 |
The Application of the Cahn-Ingold-Prelog Sequence Rules to Labelled Compounds | p. 63 |
The Stereochemistry of Reactions Used in Labelling | p. 64 |
Labelled Steroids | p. 69 |
Labelled Gibberellin Plant Hormones | p. 73 |
The Chiral Methyl Group | p. 75 |
Stereospecifically Labelled Mevalonic Acid | p. 78 |
Stereospecifically Labelled Isopentenyl Diphosphate | p. 81 |
Labelling of 1-Deoxy-D-xylulose | p. 83 |
The Stereochemistry of Hydrogen Transfer from the Nicotinamide Coenzymes | p. 84 |
The Synthesis of Labelled Amino Acids | p. 86 |
Introduction | p. 86 |
The Synthesis of Racemic Labelled Amino Acids | p. 87 |
Labelled Enantiopure Amino Acids | p. 89 |
The Labelling of Some Compounds of Pharmaceutical Interest | p. 96 |
Introduction | p. 96 |
Lidocaine | p. 97 |
Non-steroidal Anti-inflammatory Agents | p. 98 |
Amphetamines | p. 101 |
Sulfonamides | p. 102 |
Morphine and Its Relatives | p. 103 |
Galanthamine | p. 106 |
Tropane Alkaloids | p. 107 |
Tryptamine Derivatives | p. 108 |
Labelling Compounds with the Stable Isotopes of Nitrogen and Oxygen | p. 110 |
Nitrogen-15 | p. 110 |
Oxygen-17 and Oxygen-18 | p. 116 |
Labelling with Isotopes of Phosphorus, Sulfur and the Halogens122 | |
Phosphorus-32 | p. 122 |
Sulfur-34 and Sulfur-35 | p. 124 |
Chlorine-36 | p. 126 |
Iodine Isotopes | p. 126 |
Labelling Organic Compounds for Diagnostic Imaging | p. 129 |
Introduction | p. 129 |
Positron Emission Tomography | p. 129 |
Carbon-11 in PET | p. 131 |
Fluorine-18 in PET | p. 135 |
Nitrogen-13 in PET | p. 141 |
Oxygen-15 in PET | p. 141 |
Isotopes of Bromine | p. 141 |
Positron-emitting Metallic Isotopes in PET | p. 142 |
Single Photon Emission Computed Tomography | p. 143 |
Technetium-99m | p. 143 |
Iodine-123 | p. 144 |
Conclusion | p. 146 |
Further reading | p. 149 |
Glossary | p. 161 |
Appendix | p. 167 |
Subject Index | p. 172 |
Table of Contents provided by Ingram. All Rights Reserved. |
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