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1st Edition

Carbocation Chemistry Applications in Organic Synthesis

Edited By Jie Jack Li Copyright 2017
    ISBN 9780367873462
    224 Pages
    Published December 10, 2019 by CRC Press

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    Original Price $94.95
    Sale Price USD $75.96
    ISBN 9781498729086
    222 Pages 379 B/W Illustrations
    Published October 13, 2016 by CRC Press

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    Original Price $240.00
    Sale Price USD $192.00
    ISBN 9781315370248
    222 Pages 379 B/W Illustrations
    Published October 3, 2016 by CRC Press

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    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.

    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


    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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