| 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 |
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