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

Chapter Five - Synthesis and Reactions of Difluoroallylic Compounds 114
5.1 Introduction 114
5.1.1 Difluoromethylene Synthons 114
5.1.2 Difluoroallylanions 116
5.2 Results and discussion 119
5.2.1 Synthesis of 2,2-difluoro-1-phenylbut-3-en-1-ol (158) 119
5.2.2 Synthesis of difluoroallylic esters 120
5.2.3 Synthesis of Derivatised Difluoro phenyl alcohols 123
5.2.4 Synthesis of Allylic Difluorides 126
5.2.5 Metal-Mediated Synthesis of 3,3-difluoro-2-phenylpent-4-en-2-ol (181) 128
5.2.6 Reactions of Difluoroallylic Products with Palladium(0) 129
5.3 Conclusions 131
5.4 References 133
Chapter Six- Experimental Details 135
6.1 General Experimental Procedures 135
6.1.1 Nuclear Magnetic Resonance Spectroscopy 135
6.1.2 Mass spectroscopy 136
6.1.3 Infrared Spectroscopy 136
6.1.4 Elemental Analysis 136
6.1.5 X-Ray Crystallography 136
6.1.6 Starting materials 136
6.2 Experimental Details for Chapter 2 137
6.2.1 Preparation of 2-Allyl-isoindole-1,3-dione (66) 137
6.2.2 Preparation of Allyl Benzoate (67) 137
6.2.3 Preparation of allyl 4-methylbenzoate (85) 138
6.2.4 Preparation of allyl 4-fluorobenzoate (81) 138
6.2.5 Preparation of allyl 3-fluorobenzoate (82) 138
6.2.6 Preparation of allyl 2-fluorobenzoate (83) 140
6.2.7 Preparation of allyl 4-(trifluoromethyl)benzoate (84) 141
6.2.8 Preparation of But-3-en-2-yl benzoate (87) 141
6.2.9 Preparation of 2-methylbut-3-en-2-yl benzoate (86) 142
6.2.10 Preparation of (3-[1,3]Dioxalan-2-yl-allyl)trimethylsilane (69) 143
6.2.11 Preparation of (4-Benzyloxy-but-2-enyl)-trimethylsilane (68) 143
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