2.4 References 68 Chapter Two [1] R. Roig, J. M. Percy, in Science <strong>of</strong> <strong>Syn<strong>the</strong>sis</strong>, Georg Thieme Verlag, Stuttgart, New York, 2005, pp. 319. [2] W. J. Middleton, J. Org. Chem. 1975, 40, 574. [3] G. A. Olah, M. Nojma, I. Kerekes, J. Am. Chem. Soc. 1974, 96, 925. [4] A. Boukerb, D. Grée, M. Laabassi, R. Grée, J. Fluorine Chem 1998, 88, 23. [5] D. Grée, L. Vallerie, R. Grée, L. Toupet, I. Washington, J.-P. Pelicier, M. Villacampa, J. M. Pérez, K. N. Houk, J. Org. Chem. 2001, 66, 2374. [6] G. M. Blackburn, D. E. Kent, J. Chem. Soc. Chem. Commun. 1981, 511. [7] G. M. Blackburn, D. E. Kent, J. Chem. Soc., Perkin Trans 1 1986, 913. [8] G. B. Hammond, D. J. deMendonca, J. Fluorine Chem 2000, 102, 189. [9] J. Mann, G. P. Smith, J. Chem. Soc. Perkin Trans. 1 1991, 2884. [10] S. Legoupy, C. Crévisy, J.-C. Guillemin, R. Grée, J. Fluorine Chem 1999, 93, 171. [11] D. M. Grée, C. J. M. Kermarrec, J. T. Martelli, R. L. Grée, J.-P. Lellouche, L. J. Toupet, J. Org. Chem. 1996, 61, 1918. [12] F. Munyemana, A.-M. Frisque-Hesbain, A. Devos, L. Ghosez, Tetrahedron Lett. 1989, 30, 3077. [13] N. Yoneda, T. Fukuhara, Chem. Lett. 2001, 222. [14] J. Ichihara, T. Matsuo, T. Hanafusa, T. Ando, J. Chem. Soc. Chem. Commun. 1986, 793. [15] J. Ichihara, Y. Takai, K. Tomioka, J. Fluorine Chem 1995, 71, 131. [16] M. C. Pacheco, S. Purser, V. Gouverneur, Chem. Rev. 2008, 108, 1943. [17] V. Gouverneur, B. Greedy, Chem. Eur. J. 2002, 8, 767. [18] S. Thibaudeau, V. Gouverneur, Org. Lett. 2003, 5, 4891. [19] M. Tredwell, K. Tenza, M. C. Pacheco, V. Gouverneur, Org. Lett. 2005, 7, 4495. [20] B. Greedy, J. M. Paris, T. Vidal, V. Gouverneur, Angew. Chem. Int. Ed. 2003, 42, 3291. [21] S. Sunghee, G. C. Fu, J. Am. Chem. Soc. 2008, 130, 2756. [22] R. J. Fox, G. Lalic, R. G. Bergmann, J. Am. Chem. Soc. 2007, 129, 14144. [23] W. G. Young, F. F. Caserio, D. D. Br<strong>and</strong>on, J. Am. Chem. Soc. 1960, 82, 6163. [24] W. S. Johnson, T. Li, C. A. Harbert, W. R. Bartlett, T. R. Herrin, B. Staskun, D. H. Rich, J. Am. Chem. Soc. 1970, 92, 4461. [25] E. Meléndez, M. Pardo, Bull. Soc. Chim. Fr. 1974, 632. [26] E. J. Corey, D. E. Cane, L. Libit, J. Am. Chem. Soc. 1971, 93, 7016. [27] B. M. Trost, D. F. Taber, J. B. Alper, Tetrahedron Lett. 1976, 3857.
[28] D. F. Taber, J. Am. Chem. Soc. 1977, 99, 3513. [29] E. J. Corey, C. U. Kim, M. Takeda, Tetrahedron Lett. 1972, 4339. [30] E. W. Collington, A. I. Meyers, J. Org. Chem. 1971, 36, 3044. [31] A. I. Meyers, E. W. Collington, Tetrahedron 1971, 27, 5979. [32] S. G. Hegde, M. K. Vogel, J. Saddler, T. Hrinyo, N. Rockwell, R. Haynes, M. Oliver, J. Wolinky, Tetrahedron Lett. 1980, 21, 441. 69 Chapter Two [33] M. P. VanBrunt, R. O. Ambenge, S. M. Weinreb, J. Org. Chem. 2003, 68, 3323. [34] J. A. Tunge, S. R. Mellegard, Org. Lett. 2004, 6, 1205. [35] M. Yamanaka, M. Arisawa, A. Nishida, M. Nakawaga, Tetrahedron Lett. 2002, 43, 2403. [36] F. J. Moreno-Dorado, F. M. Guerra, F. L. Manzano, F. J. Aladro, Z. D. Jorge, G. M. Massanet, Tetrahedron Lett. 2003, 44, 6691. [37] C. Walling, W. Thaler, J. Am. Chem. Soc. 1961, 83, 3877. [38] T. Hori, K. B. Sharpless, J. Org. Chem. 1979, 44, 4204. [39] T. Hori, K. B. Sharpless, J. Org. Chem. 1979, 44, 4208. [40] F. F. Caserio, G. E. Denis, R. H. DeWolfe, W. G. Young, J. Am. Chem. Soc. 1955, 77, 4182. [41] E. I. Snyder, J. Org. Chem. 1972, 37, 1466. [42] R. M. Magid, O. S. Fruchey, W. L. Johnson, Tetrahedron Lett. 1977, 2999. [43] P.-T. Ho, N. Davies, J. Org. Chem. 1984, 49, 3027. [44] V. K. Yadav, K. G. Babu, Tetrahedron 2003, 59, 9111. [45] S. Roy, T. Das, M. Saha, S. K. Chaudhuri, S. Bhar, Synth. Commun. 2007, 37, 4367. [46] L. De Luca, G. Giacomelli, A. Porcheddu, Org. Lett. 2002, 4, 553. [47] J. Yin, C. E. Gallis, J. D. Chisholm, J. Org. Chem. 2007, 72, 7054. [48] L. Hintermann, F. Lang, P. Maire, A. Togni, Eur. J. Inorg. Chem. 2006, 1397. [49] A. Abulikemu, G. Halasz, A. Csampai, A. Gomory, J. Rabai, J. Fluorine Chem 2004, 125, 1143. [50] K. Yasui, K. Fugami, S. Tanaka, Y. Tamaru, J. Org. Chem. 1995, 60, 1365. [51] G. W. Ebert, W. L. Juda, R. H. Kosakowski, B. Ma, L. Dong, K. E. Cummings, M. V. B. Phelps, A. E. Mostafa, J. Luo, J. Org. Chem. 2005, 70, 4314 [52] T. J. Deming, B. M. Novak, J. Am. Chem. Soc. 1993, 115, 9101. [53] I. Victor Paul Raj, A. Sudalai, Tetrahedron Lett. 2005, 46, 8303 [54] A. Bhattacharya, N. C. Patel, T. Vasques, R. Tichkule, G. Parmar, J. Wu, Tetrahedron Lett. 2006, 47, 565. [55] K. Nakamura, K. Takenaka, Tetrahedron: Asymmetry 2002, 13, 415. [56] B. M. Trost, C. Nübling, Carbohydr. Res. 1990, 202, 1.
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Synthesis and Comparison of the Rea
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Acknowledgements Firstly, I would l
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2.2.2.1.1 Synthesis of 1-(Benzyloxy
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6.2.12 Preparation of 2-(4-trimethy
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6.4.12 Experimental Data for Dimeth
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AgF ap Bn Bz CsF d DAST dba DCM DME
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Chapter one
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2 Chapter One potentially explosive
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4 Chapter One ortho-biphenyl trifla
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6 Chapter One 2,10 (3,3-dichlorocam
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8 Chapter One both enantiomers were
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10 Chapter One poor to moderate ena
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Scheme 1.10 Fluorination of (17) 12
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14 Chapter One fluorine donors, Lew
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1.3 Enantioselective Nucleophilic F
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116 Chapter Five The first enantios
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118 Chapter Five Gem(difluoroallyl)
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120 Chapter Five benzaldehyde, 3-br
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Starting Substrate (76) (77) (78) (
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Starting Substrate Product Yield (%
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5.2.4 Synthesis of Allylic Difluori
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5.2.5 Metal-mediated synthesis of 3
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130 Chapter Five process. [40] Unfo
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132 Chapter Five compounds were pur
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134 Chapter Five [30] H. L. Sham, N
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6.1 General Experimental Procedures
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6.2 Experimental Details for Chapte
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139 Chapter Six (1 g, 0.75 cm 3 , 6
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6.2.7 Preparation of allyl 4-(trifl
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6.2.10 Preparation of (3-[1,3]Dioxa
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145 Chapter Six reaction mixture wa
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147 Chapter Six mg, 1.1 mmol), ally
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149 Chapter Six 260.3 Hz, ArCF), 16
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6.2.22 Preparation of 2-fluorobut-3
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6.2.25 Preparation of 2-fluorobut-3
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6.2.28 Preparation of 2-hydroxybut-
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157 Chapter Six 1 JCF = 253.5 Hz, A
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159 Chapter Six drying under high v
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6.2.37 Preparation of 2-chlorobut-3
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6.2.40 Preparation of 2-chlorobut-3
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6.3.2 Preparation of Bis[�-chloro
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167 Chapter Six 6.3.5 Preparation o
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169 Chapter Six 4 JHH = 1.2 Hz, ArH
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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,
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6.4.9 Preparation of Dimethyl 2-(4-
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181 Chapter Six 6.4.13 Preparation
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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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197 Chapter Six 6.5.20 Preparation
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199 Chapter Six 6.5.22 Preparation
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Appendix
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II Appendix Second generation Grubb
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IV Appendix mixture was stirred at
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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
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XII Appendix A8 Crystal data and st
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XIV Appendix A10 Crystal data and s
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A12 Lecture Courses Attended XVI Ap
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A14 Conferences Attended RSC Organi