Synthesis and Comparison of the Reactivity of Allyl Fluorides and ...

Contents
Abstract i
Acknowledgements ii
Contents iii
List of Abbreviations x
Chapter One - Introduction 1
1.1 Types of Fluorination 1
1.1.1 Electrophilic Fluorination 1
1.1.2 Nucleophilic Fluorination 2
1.2 Chiral Fluorinating Reagents 4
1.2.1 [N-F] + Reagents 8
1.2.2 Asymmetric Catalysis 11
1.3 Enantioselective Nucleophilic Fluorination 16
1.4 Building Block Approach to Organofluorine Compounds 19
1.5 C-F Activation 23
1.5.1 Aromatic Fluorides 23
1.5.2 Alkenyl Fluorides 25
1.5.3 Aliphatic Fluorides 27
1.6 Thesis Outline 30
1.7 References 31
Chapter Two – Synthesis of Allylic Fluorides and Allylic Chlorides 35
2.1 Introduction 35
2.1.1 Synthesis of Allylic Fluorides via Nucleophilic Fluorination 35
2.1.2 Synthesis of Allylic Fluorides via Electrophilic Fluorination 39
2.1.3 Allylic Chlorides from Allylic Alcohols 42
2.2 Results and Discussion 49
2.2.1 Synthesis of Allyl Fluorides 49
2.2.1.2 Synthesis of Derivatised Allyl Benzoates 52
2.2.1.3 Synthesis of Silyl Derivatised Allyl Benzoates 56
2.2.1.4 Synthesis of Fluorinated Derivatised Allyl Benzoates 58
2.2.2 Synthesis of Allylic Chlorides 59
2.2.2.1 Synthesis of Allyl Alcohols 60
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