Carbocation Chemistry: Applications in Organic Synthesis, 1st Edition (Hardback) book cover

Carbocation Chemistry

Applications in Organic Synthesis, 1st Edition

Edited by Jie Jack Li

CRC Press

208 pages | 379 B/W Illus.

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pub: 2016-10-13
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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.

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. 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

About the Editor

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.

About the Series

New Directions in Organic & Biological Chemistry

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Subject Categories

BISAC Subject Codes/Headings:
MEDICAL / Biochemistry
SCIENCE / Chemistry / Analytic
SCIENCE / Chemistry / Organic