Molecular Rearrangements in Organic Synthesis [Hardcover]

Designed for practitioners of organic synthesis, this book helps chemists understand and take advantage of rearrangement reactions to enhance the synthesis of useful chemical compounds.

• Provides ready access to the genesis, mechanisms, and synthetic utility of rearrangement reactions
• Emphasizes strategic synthetic planning and implementation
• Covers 20 different rearrangement reactions
• Includes applications for synthesizing compounds useful as natural products, medicinal compounds, functional materials, and physical organic chemistry

LIST OF CONTRIBUTORS xvii

PREFACE xxi

PART 1 1,2-MIGRATIONS 1

1 Pinacol and Semipinacol Rearrangements in Total Synthesis 3

1.1 Introduction 3

1.2 Pinacol Reaction 4

1.3 Semipinacol Rearrangement 15

1.4 Conclusion 30

References 32

2 Baeyer–Villiger (BV) Oxidation/Rearrangement in Organic Synthesis 35

2.1 Introduction 35

2.2 Mechanism 35

2.3 Synthetic Applications 37

2.4 Summary and Outlook 55

References 55

3 The Wolff Rearrangement: Tactics, Strategies and Recent Applications in Organic Synthesis 59

3.1 Introduction 59

3.2 Tactics and Strategies via the Wolff Rearrangement 60

3.3 Mechanistic Features and Selectivity Issues of the Wolff Rearrangement 63

3.4 Preparation of α-Diazocarbonyl Compounds 64

3.5 Recent Synthetic Applications of the Wolff Rearrangement 67

3.6 Conclusion and Outlook 80