Carbocation Chemistry: Applications in Organic Synthesis

ISBN-13: 9780367873462 / Angielski / Miękka / 2019 / 208 str.

Jie Jack Li

Opis

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 synthe

Spis treści

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 – S_N1

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 S_N1-related Reactions



9. References

Chapter 3. Nucleophilic Aliphatic Substitution – S_N2

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. Friede

O autorze

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.