Chemistry Book from C.H.I.P.S.

Organofluorine Chemistry
by Kenji Uneyama

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.

The initial chapters focus on why fluorine creates such unique properties in organic compounds and the general reactions of fluorine.

Organofluorine Chemistry then covers topics 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, Organofluorine Chemistry is a cohesive summary of the fundamental principals of organofluorine chemistry.


1. Fundamentals in Organic Fluorine Chemistry

  1. Some Physical Properties of Organic Fluorine Compounds
  2. Electronic Effect
  3. Steric Effects of Fluorine Substituents

2. Unique Reactions Induced by Fluorine

  1. Nucleophilic Substitution on Fluoroaromatic Rings
  2. SN2’ Reactions of Alkenes Bearing Trifluoromethyl Group
  3. Nucleophilic Substitution on Gem-Difluoromethylene Carbon
  4. Single electron transfer (SET) reaction of perfluoroalkyl Halides
  5. Fluorine-Activated Electrophilic Reagents (F-X and XFn)

3. Reactions Activated By a Atrong Interaction Between Fluorine and Other Atoms

  1. Reaction Induced by F-Li Interaction
  2. Reaction Induced by F-Al Interaction
  3. Reaction Induced by F-Si Interaction
  4. Reaction Induced by F-B Interaction
  5. Other Examples (Sm, Yb, Zr, Hf)

4. Hydrogen Bonding in Organofluorine Compounds

  1. Organofluorine as a Hydrogen-Bonding Acceptor
  2. Hydrogen Bonding of ß-fluorinated Alcohols, Its Structural Character, and Utilization in Organic Synthesis
5. Fluorinated Ligands for Selective Catalytic Reactions

  1. Ligands with Fluorine-Substituted Aryl Groups
  2. Ligands and Auxiliaries with Fluorinated Alkyl Groups
  3. Fluorinated Ligands Usable for Catalytic Reactions in scCO2 and Fluorous Solvents

6. Fluorine in Drug Designs

  1. Electron-withdrawing Effect
  2. Electron-withdrawing Effect for Lowering Basicity of Amines
  3. π-π Stacking of Polyfluorinated Aromatic Rings
  4. Interaction of Fluorine in the C-F Bond with an Electron-Deficient Center
  5. Metabolic Blocking
  6. Increased Hydrophobicity of Fluoroaryl Groups
  7. Mechansim-based Design of Bioactivie Molecules
  8. Fluoroalkenes as Isosteres of the Amide Bond

7. Methods for Introduction of Fluorine-Functionality into Molecules

  1. Monofluorination
  2. Difluorination
  3. Trifluoromethylation
  4. Perfluoroalkylation


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Organofluorine Chemistry
by Kenji Uneyama
2006 • 339 pages • $219.00 + shipping
Texas residents please add 6.75 % sales tax

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