Guide to Fluorine NMR for Organic Chemists

PREFACE. 1 GENERAL INTRODUCTION. 1.1. Why Fluorinated Compounds are Interesting. 1.2. Introduction to Fluorine NMR. References. 2 AN OVERVIEW OF FLUORINE NMR. 2.1. Introduction. 2.2. Fluorine Chemical Shifts. 2.3. Spin-Spin Coupling Constants to Fluorine. 2.4. 1 H Spectra of Fluoroorganic Compounds. 2.5. 13 C NMR Spectra of Fluoroorganic Compounds. 2.6. Isotope Effects on Chemical Shifts. 2.7. Advanced Topics. References. 3 THE SINGLE FLUORINE SUBSTITUENT. 3.1. Introduction. 3.2. Saturated Hydrocarbons. 3.3. Influence of Substituents/Functional Groups. 3.4. Carbonyl Functional Groups. 3.5. Nitriles. 3.6. Alkenes with a Single Fluorine Substituent. 3.7. Acetylenic Fluorine. 3.8. Allylic, Propargylic, and Benzylic Fluorides. 3.9. Fluoroaromatics. 3.10. Fluoroheterocycles. 3.11. Other Common Groups with a Single Fluorine Substituent. References. 4 THE CF 2 GROUP. 4.1. Introduction. 4.2. Saturated Hydrocarbons Containing a CF 2 Group. 4.3. Influence of Substituents/Functional Groups. 4.4. Carbonyl Functional Groups. 4.5. Nitriles. 4.6. Bifunctional CF 2 Compounds. 4.7. Alkenes and Alkynes. 4.8. Benzenoid Aromatics Bearing a CF 2 Group. 4.9. Heteroaromatic CF 2 Groups. References. 5 THE TRIFLUOROMETHYL GROUP. 5.1. Introduction. 5.2. Saturated Hydrocarbons Bearing a CF 3 Group. 5.3. Influence of Substituents and Functional Groups. 5.4. Carbonyl Compounds. 5.5. Nitriles. 5.6. Bifunctional Compounds. 5.7. Sulfonic Acid Derivatives. 5.8. Allylic and Propargylic Trifluoromethyl Groups. 5.9. Aryl-Bound Trifluoromethyl Groups. 5.10. Heteroaryl-Bound Trifluoromethyl Groups. References. 6 MORE HIGHLY FLUORINATED GROUPS. 6.1. Introduction. 6.2. The 1,1,2- and 1,2,2-Trifluoroethyl Groups. 6.3. The 1,1,2,2-Tetrafluoroethyl and 2,2,3,3-Tetrafluoropropyl Groups. 6.4. The 1,2,2,2-Tetrafluoroethyl Group. 6.5. The Pentafluoroethyl Group. 6.6. The 2,2,3,3,3-Pentafluoropropyl Group. 6.7. The 1,1,2,3,3,3-Hexafluoropropyl Group. 6.8. The Hexafluoro- iso -Propyl Group. 6.9. The Heptafluoro- n -Propyl Group. 6.10. The Heptafluoro- iso -Propyl Group. 6.11. The Nonafluoro- n -Butyl Group. 6.12. Fluorous Groups. 6.13. 1-Hydro-Perfluoroalkanes. 6.14. Perfluoroalkanes. 6.15. Perfluoro- n -Alkyl Halides. 6.16. Perfluoroalkyl Amines, Ethers, and Carboxylic Acid Derivatives. 6.17. Polyfluoroalkenes. 6.18. Polyfluorinated Aromatics. 6.19. Polyfluoroheterocyclics. References. 7 COMPOUNDS AND SUBSTITUENTS WITH FLUORIDE DIRECTLY BOUND TO A HETEROATOM. 7.1. Introduction. 7.2. Boron Fluorides. 7.3. Fluorosilanes. 7.4. Nitrogen Fluorides. 7.5. Phosphorous Fluorides. 7.6. Oxygen Fluorides (Hypofluorites). 7.7. Sulfur Fluorides. 7.8. The Pentafluorosulfanyl (SF 5 ) Group. 7.9. Bromine Trifluoride and Iodine Pentafluoride. 7.10. Aryl Halogen Difluorides and Tetrafluorides. 7.11. Xenon Difluoride. References. GENERAL INDEX. COMPOUND INDEX.