Organofluorine Chemistry
1. Edition April 2006
352 Pages, Hardcover
Wiley & Sons Ltd
The 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.
These molecules are of interest across the wide spectrum of
industrial and academic organic chemistry, so that organofluorine
chemistry is economically highly important.
Organofluorine Chemistry will help chemists to develop a
systematic knowledge of the chemistry of fluorine with a view
towards its application in the design of new reactions and
syntheses, and the creation of novel fluorinated molecules and
materials. With initial chapters focusing on why fluorine creates
such unique properties in organic compounds, the book then covers
general reactions of fluorine. Coverage is chosen from the recent
research literature, concentrating on the development of novel
bioactive compounds and catalytic ligands, and explaining, in the
context of the initial chapters, how and why fluorine is so
effective. With a final chapter covering the general synthetic
chemistry of organofluorine compounds, the book is a cohesive
summary of the fundamental principals of organofluorine
chemistry.
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
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
