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

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6.5.3 References 200 Appendix I A1 Attempted Reactions in Chapter 2 I A2 Attempted Reactions in Chapter 3 II A3 Attempted Reactions in Chapter 4 V A4 Attempted Reactions in Chapter 5 VI A5 Crystal data and structure refinement for 2-hydroxybut-3-enyl 4- (trifluoromethyl) benzoate (104) A6 Crystal data and structure refinement for 2-hydroxybut-3-enyl 4- methylbenzoate (105) A7 Crystal data and structure refinement for 2-hydroxybut-3-enyl 4- fluorobenzoate (101) A8 Crystal data and structure refinement for Bis[�-chloro-bis(butenyl- (1,2,3-�)-4-fluorobenzoate] dipalladium (127) A9 Crystal data and structure refinement for Bis[�-chloro-bis(butenyl- (1,2,3-�)-3-fluorobenzoate] dipalladium (128) A10 Crystal data and structure refinement for 2-(2-fluorobut-3-enyl) isoindoline-1,3-dione (74) A11 Crystal data and structure refinement for Palladium(II) Acetylacetonate (144) A12 Lecture Courses Attended XVI A13 Organic/Inorganic Seminar Programme XVI A14 Conferences Attended XVIII A15 Presentations XVIII A16 References XIX ix IX X XI XII XIII XIV XV
AgF ap Bn Bz CsF d DAST dba DCM DME DMF DMSO dppf dppp EI ee Et FAB F-TEDA Hz J KH KF LDA LHMDS m Me MeCN mp NaF NaH NFSI NMR Silver fluoride Apparent Benzyl Benzoate Caesium fluoride Doublet Abbreviations Diethylaminosulfur trifluoride dibenzylideneacetone Dichloromethane Dimethoxyethane N,N-Dimethylformamide Dimethyl sulfoxide 1,1’-bis(diphenylphosphino)ferrocene 1,3-bis(diphenylphosphino)propane Electron Impact Enantiomeric excess Ethyl Fast atom bombardment Selectfluor Hertz Coupling Constant Potassium hydride Potassium fluoride Lithium diisopropylamide Lithium bis(trimethylsilyl)amide Multiplet Methyl Acetonitrile Melting point Sodium fluoride Sodium hydride N-Fluorobenzenesulfonimide Nuclear magnetic resonance x
Page 1 and 2: Synthesis and Comparison of the Rea
Page 3 and 4: Acknowledgements Firstly, I would l
Page 5 and 6: 2.2.2.1.1 Synthesis of 1-(Benzyloxy
Page 7 and 8: 6.2.12 Preparation of 2-(4-trimethy
Page 9: 6.4.12 Experimental Data for Dimeth
Page 13 and 14: Chapter one
Page 15 and 16: 2 Chapter One potentially explosive
Page 17 and 18: 4 Chapter One ortho-biphenyl trifla
Page 19 and 20: 6 Chapter One 2,10 (3,3-dichlorocam
Page 21 and 22: 8 Chapter One both enantiomers were
Page 23 and 24: 10 Chapter One poor to moderate ena
Page 25 and 26: Scheme 1.10 Fluorination of (17) 12
Page 27 and 28: 14 Chapter One fluorine donors, Lew
Page 29 and 30: 1.3 Enantioselective Nucleophilic F
Page 31 and 32: Scheme 1.16 Fluorination of (32) 18
Page 33 and 34: 20 Chapter One (iii) SN2’ type su
Page 35 and 36: 22 Chapter One cytotoxicity in the
Page 37 and 38: 24 Chapter One Manabe and Ishikawa
Page 39 and 40: Scheme 1.25 Synthesis of (41)-(44)
Page 41 and 42: Figure 1.12 �-fluorinated NSAIDs
Page 43 and 44: 1.6 Thesis Outline 30 Chapter One T
Page 45 and 46: 32 Chapter One [26] M. Abdul-Ghani,
Page 47 and 48: [79] M. Schlosser, D. Michael, Z.-W
Page 49 and 50: 2.1 Introduction 2 Synthesis of All
Page 51 and 52: 37 Chapter Two In dehydroxyfluorina
Page 53 and 54: Scheme 2.6 Fluorination with IF5/Et
Page 55 and 56: 41 Chapter Two desired allylic fluo
Page 57 and 58: 43 Chapter Two c) Formation of a su
Page 59 and 60: Scheme 2.14 Reaction of cis-3-methy
Page 61 and 62:
Substrate (60) (61) (62) (63) R = O
Page 63 and 64:
Alcohol Product Yield (%) Table 2.7
Page 65 and 66:
51 Chapter Two completion. This ena
Page 67 and 68:
53 Chapter Two Chapter Three. Follo
Page 69 and 70:
55 Chapter Two Two allyl alcohols w
Page 71 and 72:
57 Chapter Two The conversion of (8
Page 73 and 74:
Starting substrate (88) (89) (90) (
Page 75 and 76:
Starting substrate (99) (76) (77) (
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63 Chapter Two Both (105) and (104)
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Scheme 2.25 Mechanistic pathway for
Page 81 and 82:
2.3 Conclusions 67 Chapter Two The
Page 83 and 84:
[28] D. F. Taber, J. Am. Chem. Soc.
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Chapter THRee
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72 Chapter Three Kurosawa reacted a
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74 Chapter Three These results demo
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76 Chapter Three More recently, wor
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3.2 Results and Discussion 3.2.1 Re
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80 Chapter Three Starting substrate
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82 Chapter Three Figure 3.4 Crystal
Page 99 and 100:
Scheme 3.12 Oxidative addition of 1
Page 101 and 102:
86 Chapter Three when the reaction
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88 Chapter Three Therefore, from th
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-140 -140 -140 -140 -140 -150 -150
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92 Chapter Three monitored for 80 m
Page 109 and 110:
3.4 References [1] W. T. Dent, R. L
Page 111 and 112:
Chapter Four
Page 113 and 114:
97 Chapter Four nucleophilic substi
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99 Chapter Four Further reactions w
Page 117 and 118:
Figure 4.3 Structure of co-product
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4.2.2 Reactions of palladium cation
Page 121 and 122:
105 Chapter Four substituents on th
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107 Chapter Four The desired produc
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109 Chapter Four The reaction of (1
Page 127 and 128:
111 Chapter Four were both reacted
Page 129 and 130:
[28] D. Landini, A. Maia, A. Rampol
Page 131 and 132:
5.1 Introduction 5 Synthesis and Re
Page 133 and 134:
116 Chapter Five The first enantios
Page 135 and 136:
118 Chapter Five Gem(difluoroallyl)
Page 137 and 138:
120 Chapter Five benzaldehyde, 3-br
Page 139 and 140:
Starting Substrate (76) (77) (78) (
Page 141 and 142:
Starting Substrate Product Yield (%
Page 143 and 144:
5.2.4 Synthesis of Allylic Difluori
Page 145 and 146:
5.2.5 Metal-mediated synthesis of 3
Page 147 and 148:
130 Chapter Five process. [40] Unfo
Page 149 and 150:
132 Chapter Five compounds were pur
Page 151 and 152:
134 Chapter Five [30] H. L. Sham, N
Page 153 and 154:
6.1 General Experimental Procedures
Page 155 and 156:
6.2 Experimental Details for Chapte
Page 157 and 158:
139 Chapter Six (1 g, 0.75 cm 3 , 6
Page 159 and 160:
6.2.7 Preparation of allyl 4-(trifl
Page 161 and 162:
6.2.10 Preparation of (3-[1,3]Dioxa
Page 163 and 164:
145 Chapter Six reaction mixture wa
Page 165 and 166:
147 Chapter Six mg, 1.1 mmol), ally
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149 Chapter Six 260.3 Hz, ArCF), 16
Page 169 and 170:
6.2.22 Preparation of 2-fluorobut-3
Page 171 and 172:
6.2.25 Preparation of 2-fluorobut-3
Page 173 and 174:
6.2.28 Preparation of 2-hydroxybut-
Page 175 and 176:
157 Chapter Six 1 JCF = 253.5 Hz, A
Page 177 and 178:
159 Chapter Six drying under high v
Page 179 and 180:
6.2.37 Preparation of 2-chlorobut-3
Page 181 and 182:
6.2.40 Preparation of 2-chlorobut-3
Page 183 and 184:
6.3.2 Preparation of Bis[�-chloro
Page 185 and 186:
167 Chapter Six 6.3.5 Preparation o
Page 187 and 188:
169 Chapter Six 4 JHH = 1.2 Hz, ArH
Page 189 and 190:
Time (minutes) 4 11 18 25 Table 6.2
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Time (minutes) 19 F{ 1 H} (ppm) Tim
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175 Chapter Six suspension of sodiu
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177 Chapter Six Hz, Ha), 5.19 (1H,
Page 197 and 198:
6.4.9 Preparation of Dimethyl 2-(4-
Page 199 and 200:
181 Chapter Six 6.4.13 Preparation
Page 201 and 202:
6.5 Experimental Details for Chapte
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185 Chapter Six CHCH2), 133.9 (d, 3
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187 Chapter Six 6.5.6 Preparation o
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189 Chapter Six (5 mg, 0.27 mmol) a
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191 Chapter Six (d, 1 JCF = 255.0 H
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193 Chapter Six layer separated and
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195 Chapter Six Hz, 4 JHF = 3.2 Hz,
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Page 217 and 218:
Page 219 and 220:
Appendix
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II Appendix Second generation Grubb
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IV Appendix mixture was stirred at
Page 225 and 226:
VI Appendix stirred at room tempera
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VIII Appendix The organic phase was
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X Appendix A6 Crystal data and stru
Page 231 and 232:
XII Appendix A8 Crystal data and st
Page 233 and 234:
XIV Appendix A10 Crystal data and s
Page 235 and 236:
A12 Lecture Courses Attended XVI Ap
Page 237 and 238:
A14 Conferences Attended RSC Organi
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