Description
Book SynopsisThe replacement of hydrogen with fluorine in organic molecules can profoundly influence their chemical and physical properties, leading to a range of compounds with highly desirable properties.
Trade ReviewI strongly recommend it to every practitioner of organofluorine chemistry.
...this book is a detailed and thorough review as well as a valuable source of information with numerous tables, detailed formula schemes, some helpful illustrations, and well referenced citations from the recent literature. Graduate students and research chemists working in the field should read this book to deepen their understanding of organofluorine chemistry and in particular to gain more insight into their enormous synthetic potential.
Journal of the American Chemical Society VOL. 128, NO. 51, 2006
This book is well written and with plenty of useful references.
Organic Process Research and Development Journal
Table of ContentsPreface.
1. Fundamentals in organic fluorine chemistry.
1.1 Some physical properties of organic fluorine compounds.
1.2 Electronic effect.
1.2.1 Electronic effects of the fluorine atom – insight from Hammett substituent.
constants.
1.2.2 Electronic effects on acidity, bond length, and bond energy of fluoroorganic.
molecules.
1.2.3 Halogen bonding.
1.2.4 Electronic effect to the destabilization of carbonyl and imono groups.
1.2.5 p-p Stacking of fluoroaromatics.
1.2.6 Increased p-character (Bent’s rule) and low-lying LUMO in carbon-fluorine.
bonding orbitals.
1.2.7 Negative hyperconjugation.
1.2.8 Electron-donating effect (Stabilization of carbocation).
1.2.9 Effect of fluorine substituents to the structure, stability, and reactivity of.
fluoroalkyl radicals.
1.3 Steric effects of fluorine substituents.
2. Unique reactions induced by fluorine.
2.1 Nucleophilic substitution on fluoroaromatic rings.
2.2 SN2’ reactions of alkenes bearing trifluoromethyl group.
2.3 Nucleophilic substitution on gem-difluoromethylene carbon.
2.4 Single electron transfer (SET) reaction of perfluoroalkyl halides.
2.5 Fluorine-activated electrophilic reagents (F-X and XFn).
3. Reactions activated by a strong interaction between fluorine and other atoms.
3.1 Reaction induced by F-Li interaction.
3.2 Reaction induced by F-Al interaction.
3.3 Reaction induced by F-Si interaction.
3.4 Reaction induced by F-B interaction.
3.5 Other examples (Sm, Yb, Zr, Hf).
4. Hydrogen bonding in organofluorine compounds.
5. Fluorinated ligands for selective catalytic reactions.
6. Fluorine in drug designs.
7. Methods for introduction of fluorine-functionality into molecules.
(Summary from publications for the latest fifteen years).
7.1 Monofluorination.
7.2 Difluorination.
7.3 Trifluoromethylation.
7.4 Perfluoroalkylation.
Index
