1st Edition

Carbocation Chemistry
Applications in Organic Synthesis

Edited By

Jie Jack Li





ISBN 9780367873462
Published December 10, 2019 by CRC Press
222 Pages

USD $84.95

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Book Description

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. Carbocation Chemistry: Applications in Organic Synthesis provides a panoramic view of carbocation chemistry with an emphasis on synthetic applications.

This book is an invaluable tool for organic, medicinal and analytical chemists, including those working in biochemistry as well as the petroleum, plastics and pharmaceutical industries. It is also suitable for upper level undergraduates and graduates in organic chemistry, biochemistry and medicinal chemistry.

Table of Contents



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. Friede

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Editor(s)

Biography

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.