Carbocation Chemistry

Jie Jack Li earned his Ph.D. in organic chemistry in 1995 at Indiana University. After a stint as a postdoctoral fellow at MIT, he worked as a medicinal chemist at Pfizer and Bristol-Myers Squibb from 1997 to 2012. Since then he has been an Associate Professor of Chemistry at the University of San Francisco teaching organic and medicinal chemistry. He has published 23 books ranging from organic and medicinal chemistry, to the history of drug discovery.

Chapter 1. Introduction



Nomenclature, Structure, and Stability
Generation of Carbocations
The Non-Classical Ion Controversy
Electrophilic Addition to Alkenes
Electrophilic Aromatic Substitution
Elimination reactions
Rearrangement Reactions of Carbocations
References

Chapter 2. Nucleophilic Aliphatic Substitution – SN1



Introduction
-Activated Alcohols—Brønsted Acids
-Activated Alcohols—Lewis Acids
Alkylation of Aldehydes and Ketones
Glycosylation
Friedel–Crafts Alkylation and Acylation
Electrophilic Fluorination Using Fluoronium Ion
Miscellaneous SN1-related Reactions
References

Chapter 3. Nucleophilic Aliphatic Substitution – SN2



Construction of Quaternary Stereogenic Centers
Sulfur Chemistry
Organometallic Chemistry
Macrocyclization
Glycosylation
Nucleoside Analogues
N-Alkylation
Cyclotetraphosphazenes
Conformationally Locked Tetrahydropyran Ring
The Ionic Liquid Effect
Silver Chemistry
References

Chapter 4. Electrophilic Addition to Alkenes



Introduction
Cyclopropanation
Hydroboration/Oxidation
The Pauson–Khand Reaction
Prins Reaction
Schmidt Reaction
Halogenation
Oxymercuration/Reduction
Epoxidation
Gold-Catalyzed Alkyne Hydration
Conclusion
References

Chapter 5. Electrophilic Aromatic Substitution



Introduction
Nitration
Halogenation
Friedel–Crafts Alkylation
Friedel–Crafts Acylation
Applications of Friedel–Crafts Reaction on Total Synthesis
Miscellaneous Electrophilic Aromatic Substitution Reactions
References

Chapter 6. Fragmentation and Rearrangement Reactions



Claisen Rearrangements
Cope Rearrangements
Cope Rearrangements
Aldehyde (or Ketone) Formation Rearrangements
Carboxylic Acid Formation Rearrangements
Alcohol Formation Rearrangements
Amine Formation Rearrangement
Amides
Hydrocarbon Rearrangements
Oxacyclic, Carbocyclic, Oxazoles, Tetrahydrapuran and Tetrahydropuran Formation Rearrangements
Rearrangements resulting in less common functional groups
Fragmentations
References