Organic chemistry is the science of carbon-containing compounds. There are four major types of reactive intermediates in organic chemistry: carbocations, carboanions, radicals and carbenes. Therefore, carbocation chemistry is not only fundamental to the advancement of organic chemistry, it also has found widespread applications in organic synthesis. It is not an exaggeration to say that carbocation chemistry is part of the foundation of organic chemistry. This book provides a panoramic view of carbocation chemistry with an emphasis on synthetic applications.
Organic chemistry is the science of carbon-containing compounds. There are four major types of reactive intermediates in organic chemistry: carbocations, carboanions, radicals and carbenes. Therefore, carbocation chemistry is not only fundamental to the advancement of organic chemistry, it also has found widespread applications in organic synthesis. It is not an exaggeration to say that carbocation chemistry is part of the foundation of organic chemistry. This book provides a panoramic view of carbocation chemistry with an emphasis on synthetic applications.
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.
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Chapter 1. Introduction 1. Nomenclature, Structure, and Stability 2. Generation of Carbocations 3. The Non-Classical Ion Controversy 4. Electrophilic Addition to Alkenes 5. Electrophilic Aromatic Substitution 6. Elimination reactions 7. Rearrangement Reactions of Carbocations 8. References Chapter 2. Nucleophilic Aliphatic Substitution - SN1 1. Introduction 2. -Activated Alcohols-Brønsted Acids 3. -Activated Alcohols-Lewis Acids 4. Alkylation of Aldehydes and Ketones 5. Glycosylation 6. Friedel-Crafts Alkylation and Acylation 7. Electrophilic Fluorination Using Fluoronium Ion 8. Miscellaneous SN1-related Reactions 9. References Chapter 3. Nucleophilic Aliphatic Substitution - SN2 1. Construction of Quaternary Stereogenic Centers 2. Sulfur Chemistry 3. Organometallic Chemistry 4. Macrocyclization 5. Glycosylation 6. Nucleoside Analogues 7. N-Alkylation 8. Cyclotetraphosphazenes 9. Conformationally Locked Tetrahydropyran Ring 10. The Ionic Liquid Effect 11. Silver Chemistry 12. References Chapter 4. Electrophilic Addition to Alkenes 1. Introduction 2. Cyclopropanation 3. Hydroboration/Oxidation 4. The Pauson-Khand Reaction 5. Prins Reaction 6. Schmidt Reaction 7. Halogenation 8. Oxymercuration/Reduction 9. Epoxidation 10. Gold-Catalyzed Alkyne Hydration 11. Conclusion 12. References Chapter 5. Electrophilic Aromatic Substitution 1. Introduction 2. Nitration 3. Halogenation 4. Friedel-Crafts Alkylation 5. Friedel-Crafts Acylation 6. Applications of Friedel-Crafts Reaction on Total Synthesis 7. Miscellaneous Electrophilic Aromatic Substitution Reactions 8. References Chapter 6. Fragmentation and Rearrangement Reactions 1. Claisen Rearrangements 2. Cope Rearrangements 3. Cope Rearrangements 4. Aldehyde (or Ketone) Formation Rearrangements 5. Carboxylic Acid Formation Rearrangements 6. Alcohol Formation Rearrangements 7. Amine Formation Rearrangement 8. Amides 9. Hydrocarbon Rearrangements 10. Oxacyclic, Carbocyclic, Oxazoles, Tetrahydrapuran and Tetrahydropuran Formation Rearrangements 11. Rearrangements resulting in less common functional groups 12. Fragmentations 13. References
