My PhD dissertation - Institut Fresnel

More documents

Recommendations

Info

116 Conference Proceedings, Naples, 13 – 16 October 1996, pp. 1 – 23; Chem. Abstr. 1997, 127, 263584. [ 21] R. Luckenbach, in Dynamic Stereochemistry of Pentacoordinated Phosphorus and Related Elements, Thieme, Stuttgart, 1973, pp. 109 – 124. [ 22] H.J. Christau, F. Plénat, in The Chemistry of Organophosphorus compounds, (ed.: F.R. Hartley), S. Pataï Series Editor, Vol. 3, 1994, p. 111 – 135. [ 23] K.D. Berlin, G.B. Butler, Chem. Rev. 1960, 60, 243 – 260. [ 24] H.R. Hays, D.J. Peterson, in Organic Phosphorus Compounds, Vol. 3, (ed.: G.M. Kosolapoff, L. Maier), Wiley, New York, 1972, pp. 349 – 353. [ 25] A. Cahours, A.W. Hofmann, Liebigs Ann. Chem. 1857, 104, 1 – 19. [ 26] A. Michaelis, Liebigs Ann. Chem. 1901, 315, 43 – 103. [ 27] J. Meisenheimer, L. Lichtenstadt, Ber. Dtsch. Chem. Ges. 1911, 44, 356 – 359. [ 28] J. Meisenheimer, J. Casper, M. Höring, W. Lauter, L. Lichtenstadt, W. Samuel, Liebigs Ann. Chem. 1926, 449, 213 – 248. [ 29] L. Hey, C.K. Ingold, J. Chem. Soc. 1933, 531 – 533. [ 30] G.W. Fenton, C.K. Ingold, J. Chem. Soc. 1929, 2342 – 2357. [ 31] L. Horner, H. Hoffmann, H.G. Wippel, G. Hassel, Chem. Ber. 1958, 91, 52 – 57. [ 32] H. Hoffmann, Liebigs Ann. Chem. 1960, 634, 1 – 8. [ 33] M. Zanger, C.A. Vander Werf, W.E. McEwen, J. Am. Chem. Soc. 1959, 81, 3806 – 3807. [ 34] W.E. McEwen, in Topics in Phosphorus Chemistry, Vol. 2, (ed.: M.G. Grayson, E.J. Griffith), Interscience, New York, 1965, pp. 5 – 9. [ 35] W.E. McEwen, K.F. Kumli, A. Blade-Font, M. Zanger, C.A. Vander Werf, J. Am. Chem. Soc. 1964, 86, 2378 – 2384. [ 36] S.E. Cremer, B.C. Trivedi, F.L. Weitl, J. Org. Chem. 1971, 36, 3226 – 3231. [ 37] K.L. Marsi, J.E. Oberlander, J. Am. Chem. Soc. 1973, 95, 200 – 204. [ 38] K.L. Marsi, J. Am. Chem. Soc. 1969, 91, 4724 – 4729. [ 39] L. Horner, H. Winkler, A. Rapp, A. Mentrup, H. Hoffmann, P. Beck, Tetrahedron Lett. 1961, 2, 161 – 166. [ 40] L. Horner, H. Fuchs, H. Winkler, A. Rapp, Tetrahedron Lett. 1963, 4, 965 – 967. [ 41] J.R. Corfield, J.R. Shutt, S. Trippett, J. Chem. Soc., Chem. Commun. 1969, 789 – 790. [ 42] C.B. Parisek, W.E. McEwen, C.A. Vander Werf, J. Am. Chem. Soc. 1960, 82, 5503 – 5504. [ 43] E.A. Dennis, F.H. Westheimer, J. Am. Chem. Soc. 1966, 88, 3432 – 3433.
117 [ 44] R.S. Berry, J. Chem. Phys. 1960, 32, 933 – 938. [ 45] G. Wittig, U. Pockels, H. Dröge, Ber. Dtsch. Chem. Ges. 1938, 71, 1903 – 1912. [ 46] H. Gilman, W. Langham, A.L. Jacoby, J. Am. Chem. Soc. 1939, 61, 106 – 109. [ 47] M. Schlosser, in Organometallics in Synthesis: A Manual, (ed.: M. Schlosser), 2nd edition, Wiley, Chichester, 2002, pp. 101 – 117. [ 48] G.M. Kosolapoff, in Organophosphorus Compounds, Wiley, New York, 1950, pp. 10 – 22. [ 49] J.L. Willans, Chem. Ind. (London) 1957, 8, 235 – 236. [ 50] H. Gilman, C.C. Vernon, J. Am. Chem. Soc. 1926, 48, 1063 – 1066. [ 51] D.B. Denney, F.J. Gross, J. Org. Chem. 1967, 32, 2445 – 2447. [ 52] H.R. Hays, R.G. Laughlin, J. Org. Chem. 1967, 32, 1060 – 1063. [ 53] F. Leroux, unpublished results, 2001. [ 54] F. Leroux, unpublished results, 2000. [ 55] M. Kranz, T. Clark, P.V.R. Schleyer, J. Org. Chem. 1993, 58, 3317 – 3325. [ 56] K.J. Brown, M.S. Berry, K.C. Waterman, D. Lingenfelter, J.R. Murdoch, J. Am. Chem. Soc. 1984, 106, 4717 – 4123. [ 57] K.J. Brown, J.R. Murdoch, J. Am. Chem. Soc. 1984, 106, 7843 – 7845. [ 58] U. Schubert, W. Neugebauer, P.v.R. Schleyer, J. Chem. Soc., Chem. Commun. 1982, 1184 – 1185. [ 59] O. Desponds, M. Schlosser, Tetrahedron 1994, 50, 5881 – 5888. [ 60] A.M. Echavarren, D.J. Cárdenas, in Metal-Catalyzed Cross-Coupling Reactions (eds.: A. de Meijeire, F. Diederich), Vol. 1, Wiley, Chichester, 2004, pp. 1 – 31. [ 61] K. Tamao, N. Miyaura, in Cross-Coupling Reactions, (ed.: N. Miyaura), Top. Curr. Chem., 2002, 219, Springer, Berlin, pp. 15 – 26. [ 62] D.W. Allen, B.G. Hutley, T.C. Rich, J. Chem. Soc., Perkin Trans. 2 1972, 63 – 67. [ 63] C. Santelli-Rouvier, C. Coin, L. Toupet, M. Santelli, J. Organomet. Chem. 1995, 495, 91 – 96. [ 64] A.J. Zapata, A.C. Roudon, Org. Prep. Proced. Int. 1995, 27, 567 – 568. [ 65] F. Eymery, P. Burattin, F. Mathey, P. Savignac, Eur. J. Org. Chem. 2000, 2425 – 2431. [ 66] H. Gilman, C.G. Stuckwisch, J. Am. Chem. Soc. 1941, 63, 2844 – 2845. [ 67] A. Burger, N.D. Dawson, J. Org. Chem. 1951, 16, 1250 – 1254. [ 68] P. Pfeiffer, Ber. Dtsch. Chem. Ges. 1904, 37, 4620 – 4623. [ 69] H. Hibbert, Ber. Dtsch. Chem. Ges. 1906, 39, 160 – 162.
Page 1:
Various Facets of Organophosphorus
Page 5:
III Remerciements Je tiens à remer
Page 9:
3.3.6 Relevance of the Data Assesse
Page 13:
VII Literature References 115 Compo
Page 17:
IX Version Abrégée Les composés
Page 21 and 22:
1 Introduction 1 The present thesis
Page 23 and 24:
3 research groups in the field are
Page 25 and 26:
5 However, this mechanism suffers f
Page 27:
7 At first, a double bromine/lithiu
Page 30 and 31:
10 Although the most frequently emp
Page 32 and 33:
12 The preparation of the latter ph
Page 34 and 35:
protected to its dioxolane derivati
Page 36 and 37:
N (S)-14 1) NBS, THF, - 75 °C 2) -
Page 39 and 40:
3 Alkaline Decomposition of Phospho
Page 41 and 42:
3.2 Alkyl Carbanions Stabilities in
Page 43 and 44:
3.3.1 Mechanistic Discussion on the
Page 45 and 46:
25 The assumption reported by these
Page 47 and 48:
27 However, in the eventuality of a
Page 49 and 50:
29 To prepare tertiary phosphines b
Page 51 and 52:
31 Table 4. Mixed tertiary alkylpho
Page 53 and 54:
33 were comparable to those obtaine
Page 55 and 56:
35 led to the formation of di-tert-
Page 57 and 58:
37 depending on the alkyl substitue
Page 59 and 60:
39 4 A Novel Access to Atropisomeri
Page 61 and 62:
41 Since the homocoupling of the ha
Page 63 and 64:
43 Few other attempts to selectivel
Page 65 and 66:
45 The second phenol ether 36 was f
Page 67 and 68:
47 The enantiomeric purity was chec
Page 69 and 70:
49 A second purpose of this derivat
Page 71 and 72:
51 substrates considered. In conseq
Page 73 and 74:
53 Single-crystal X-ray analysis of
Page 75 and 76:
55 To convert atropisomer Ia into I
Page 77 and 78:
57 This finally allows one to use t
Page 79 and 80:
the steric bulk and charge delocali
Page 81 and 82:
61 To check the reproducibility of
Page 83:
63 Figure 9. Full lineshape analysi
Page 86 and 87:
66 suitably substituted dilithiobip
Page 89: Experimental Part
Page 92 and 93: 70 deuterochloroform (CDCl3) unless
Page 94 and 95: 72 1 H NMR: δ = 7.32 (dddd, J = 9,
Page 96 and 97: 1 H NMR: δ = 6.96 (s, 3 H), 6.94 (
Page 98 and 99: 76 C21H21O9P (448.36) calcd. C 56.2
Page 100 and 101: 78 C12H12BrN (250.13) calcd. C 57.6
Page 102 and 103: 80 C13H13NO2 (215.25) calcd. C 72.5
Page 104 and 105: 82 3.1.1 Dialkyl-N,N-diethylaminoph
Page 106 and 107: 84 apparatus. The solution was adde
Page 108 and 109: 86 Di-tert-butylisopropylphosphine
Page 110 and 111: 88 13 C NMR: δ = 32.9 (d, J = 12 H
Page 112 and 113: 90 13 C NMR: δ = 41.5 (d, J = 61 H
Page 114 and 115: 31 P NMR: δ = 53.4 ppm. 92 C16H31O
Page 116 and 117: 94 13 C NMR: δ = 40.8 (d, J = 3 Hz
Page 118 and 119: 96 31 P NMR settings: It is known t
Page 120 and 121: 98 Theoretical ratio: (96.1:3.9) Ex
Page 123 and 124: 101 4 The Preparation and Racemate
Page 125 and 126: 103 extraction protocol with ethyl
Page 127 and 128: 105 extracted with ethyl acetate (2
Page 129 and 130: 107 (+)-(M)-Dimethyl-6,6’-dibromo
Page 131 and 132: 109 (+)-(M)-2,2’-Dibromo-6,6’-b
Page 133 and 134: 111 1 H NMR: δ = 7.2 (m, 20 H), 7.
Page 135 and 136: 113 2,2’-Dilithio-6,6’-bis(meth
Page 137: References
Page 142 and 143: 118 [ 70] J. Drowart, C.E. Myers, R
Page 144 and 145: 120 [117] S.T. Graul, R.R. Squires,
Page 146 and 147: 122 [170] B.H. Lipshutz, F. Kayser,
Page 148: 124 [212] M. Schlosser, in Organome
Page 152: O P 27i: p. 30, 80 C 9H 21OP P 26b:
Page 156: P P P O 2: p. 11, 59 3 P O O O 11:
Page 160: Nom Maurin Prénom Michaël 129 Cur
show all

My PhD dissertation - Institut Fresnel

You also want an ePaper? Increase the reach of your titles

Delete template?

Save as template?