"Front Matter". In: Organosilanes in Radical Chemistry - Index of

More documents

Recommendations

Info

References 181 The number of consecutive processes in some radical cascade processes can be really astonishing [106,107]. Two representative examples are described below [106]. Treatment of the acetylene derivative 88 with (TMS) 3SiH leads, in one pot, to the bicyclic compound 89 in a 70 % yield (Reaction 7.92). The proposed mechanism involves (TMS) 3Si: radical addition to the triple bond to form a vinyl radical followed by a remarkable cascade of radical 6-exo cyclization, fragmentation, transannulation, ring expansion, and termination via ejection of the (TMS) 3Si: radical to afford the bicyclic product. When a solution of vinyl bromide 90 was irradiated with a sunlamp in the presence of (TMS) 3SiH it gave the corresponding triquinane oxime 91 as a 1:1 mixture of a- and b-methyl diastereomers resulting from a cascade radical 6-exo cyclization, aminyl radical fragmentation, 5-exo radical transannulation, 5-exo cyclization sequence (Reaction 7.93). BzO N NR (TMS) 3SiH hν, 80 �C RN 88, R = OCH 2 Ph 89, 70% 90 7.8 REFERENCES Br (TMS) 3SiH hν, 80 �C BzO N Me H 91, 38% H (7.92) (7.93) 1. Renaud, P., and Sibi, M.P. (Eds), Radicals in Organic Synthesis, Wiley-VCH, Weinheim, 2001. 2. Curran, D.P., Porter, N.A., and Giese, B., Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications, VCH, Weinheim, 1996. 3. Renaud, P., and Gerster, M., Angew. Chem. Int. Ed. Engl., 1998, 37, 2562. 4. Sibi, M.P., and Porter, N.A., Acc. Chem. Res., 1999, 32, 163. 5. Barton, D.H.R., Half a Century of Free Radical Chemistry, Cambridge University Press, Cambridge, 1993. 6. Giese, B., Kopping, B., and Chatgilialoglu, C., Tetrahedron Lett., 1989, 30, 681. 7. Chatgilialoglu, C., Giese, B., and Kopping, B., Tetrahedron Lett., 1990, 31, 6013. 8. Schneider, H., Fiander, H., Harrison, K.A., Watson, M., Burton G.W., and Arya, P., Bioorg. Med. Chem. Lett., 1996, 6, 637. 9. Urabe, H., Kobayashi, K., and Sato, F., J. Chem. Soc. Chem. Commun., 1995, 1043. 10. Junker, H.-D., Phung, N., and Fessner, W.-D., Tetrahedron Lett., 1999, 40, 7063. Junker, H.-D., and Fessner, W.-D., Tetrahedron Lett., 1998, 39, 269.
182 Consecutive Radical Reactions 11. Togo, H., Sugi, M., and Toyama, K., C.R. Acad. Sci. Paris, Ser. IIc: Chem., 2001, 539. 12. Togo, H., Matsubayashi, S., Yamazaki, O., and Yokoyama, M., J. Org. Chem., 2000, 65, 2816. 13. Dang, H.-S., Elsegood, M.R.J., Kim, K.-M., and Roberts, B.P., J. Chem. Soc., Perkin Trans. 1, 1999, 2061. 14. Curran, D.P., Xu, J., and Lazzarini, E., J. Am. Chem. Soc., 1995, 117, 6603. 15. Curran, D.P., Xu, J., and Lazzarini, E., J. Chem. Soc., Perkin Trans. 1, 1995, 3049. 16. Ryu, I., Hasegawa, M., Kurihara, A., Ogawa, A., Tsunoi, S., and Sonoda, N., Synlett, 1993, 143. 17. Bennasar, M.-L., Roca, T., Griera, R., Bassa, M., and Bosch, J., J. Org. Chem., 2002, 67, 6268. 18. Chatgilialoglu, C., Alberti, A., Ballestri, M., Macciantelli, D., and Curran, D.P., Tetrahedron Lett., 1996, 35, 6391. 19. Martin, J. Jaramillo G., L.M., and Wang, P.G., Tetrahedron Lett., 1998, 39, 5927. 20. Minisci, F., Fontana, F., Pianese, G., and Yan, Y.M., J. Org. Chem., 1993, 58, 4207. 21. Togo, H., Hayashi, K., and Yokoyama, M., Bull. Chem. Soc. Jpn., 1994, 67, 2522. 22. Beckwith, A.L.J., and Schiesser, C.H., Tetrahedron, 1985, 41, 3925. 23. Spellmeyer, D.C., and Houk, K.N., J. Org. Chem., 1987, 52, 959. 24. Bailey, W.F., and Longstaff, S.C., Org. Lett., 2001, 3, 2217. 25. Usui, S., and Paquette, L.A., Tetrahedron Lett., 1999, 40, 3495. 26. Paquette, L.A., and Usui, S., Tetrahedron Lett., 1999, 40, 3499. 27. Chatgilialoglu, C., Crich, D., Komatsu, M., and Ryu, I., Chem. Rev., 1999, 99, 1991. 28. Lowinger, T.B., and Weiler, L., J. Org. Chem., 1992, 57, 6099. 29. Stalinski, K., and Curran, D.P., J. Org. Chem., 2002, 67, 2982. 30. Batey, R.A., and MacKay, D.B., Tetrahedron Lett., 1998, 39, 7267. 31. Salazar, K.L., and Nicholas, K.M., Tetrahedron, 2000, 56, 2211. 32. Kraus, G.A., and Liras, S., Tetrahedron Lett., 1990, 31, 5265. 33. Amrein, S., Timmermann, A., and Studer, A., Org. Lett., 2001, 3, 2357. 34. Kulicke, K.J., and Giese, B., Synlett, 1990, 91. 35. Evans, P.A., and Manangan, T., J. Org. Chem., 2000, 65, 4523. 36. Zahouily, M., Journet, M., and Malacria, M., Synlett, 1994, 366. 37. Lee, E., and Choi, S.J., Org. Lett., 1999, 1, 1127. 38. Arya, P., and Wayner, D.D.M., Tetrahedron Lett., 1991, 32, 6265. 39. Yamazaki, O., Yamaguchi, K., Yokoyama, M., and Togo, H., J. Org. Chem., 2000, 65, 5440. 40. Cossy, J., and Sallé, L., Tetrahedron Lett., 1995, 40, 7235. 41. Evans, P.A., and Roseman, J.D., J. Org. Chem., 1996, 61, 2252. 42. Evans, P.A., Murthy, V.S., Roseman, J.D., and Rheingold, A.L., Angew. Chem. Int. Ed., 1999, 38, 3175. 43. Evans, P.A., and Roseman, J.D., Tetrahedron Lett., 1997, 38, 5249. 44. Evans, P.A., Roseman, J.D., and Garber, L.T., J. Org. Chem., 1996, 61, 4880. 45. Pandey, G., Rao, K.S.S.P., Palit, D.K., and Mittal, J.P., J. Org. Chem., 1998, 63, 3968. 46. Pandey, G., Rao, K.S.S.P., and Rao, K.V.N., J. Org. Chem., 2000, 65, 4309. 47. Sasaki, K., Kondo, Y., and Maruoka, K., Angew. Chem. Int. Ed., 2001, 40, 411. 48. Ooi, T., Hokke, Y., and Maruoka, K., Angew. Chem. Int. Ed. Engl., 1997, 36, 1181. 49. Miura, K., Oshima, K., and Utimoto, K., Bull. Chem. Soc. Jpn., 1993, 66, 2348. 50. Jiao, X.-Y., and Bentrude, W.G., J. Am. Chem. Soc., 1999, 121, 6088. 51. Evans, P.A., and Leahy, D.K., J. Am. Chem. Soc., 2000, 122, 5012. 52. Ihara, M., Setsu, F., Shohda, M., Taniguchi, N., Tokunaga, Y., and Fukumoto, K., J. Org. Chem., 1994, 59, 5317.
Page 1 and 2:
Organosilanes in Radical Chemistry
Page 3 and 4:
DEDICATION To my parents XrZstoB an
Page 5 and 6:
viii Contents 3.6 Hydrogen Atom: An
Page 7 and 8:
PREFACE A large number of papers de
Page 9 and 10:
ACKNOWLEDGEMENTS I thank Keith U. I
Page 11 and 12:
2 Formation and Structures of Silyl
Page 13 and 14:
Page 15 and 16:
Page 17 and 18:
Page 19 and 20:
10 Formation and Structures of Sily
Page 21 and 22:
Page 23 and 24:
Page 25 and 26:
Page 27 and 28:
2 Thermochemistry 2.1 GENERAL CONSI
Page 29 and 30:
Bond Dissociation Enthalpies 21 Tab
Page 31 and 32:
Bond Dissociation Enthalpies 23 2.2
Page 33 and 34:
Ion Thermochemistry 25 Table 2.4 Re
Page 35 and 36:
Ion Thermochemistry 27 Table 2.5 El
Page 37 and 38:
References 29 3. Goumri, A., Yuan,
Page 39 and 40:
32 Hydrogen Donor Abilities of Sili
Page 41 and 42:
Page 43 and 44:
Page 45 and 46:
Page 47 and 48:
Page 49 and 50:
Page 51 and 52:
Page 53 and 54:
Page 55 and 56:
4 Reducing Agents 4.1 GENERAL ASPEC
Page 57 and 58:
General Aspects of Radical Chain Re
Page 59 and 60:
Tris(trimethylsilyl)silane 53 Therm
Page 61 and 62:
Tris(trimethylsilyl)silane 55 4.3.1
Page 63 and 64:
Tris(trimethylsilyl)silane 57 A goo
Page 65 and 66:
Tris(trimethylsilyl)silane 59 C(O)C
Page 67 and 68:
Tris(trimethylsilyl)silane 61 radic
Page 69 and 70:
Tris(trimethylsilyl)silane 63 86% y
Page 71 and 72:
Tris(trimethylsilyl)silane 65 RO RO
Page 73 and 74:
Tris(trimethylsilyl)silane 67 O AcO
Page 75 and 76:
Tris(trimethylsilyl)silane 69 Tris(
Page 77 and 78:
Other Silicon Hydrides 71 The reduc
Page 79 and 80:
Other Silicon Hydrides 73 The decre
Page 81 and 82:
Other Silicon Hydrides 75 Ph MeS O
Page 83 and 84:
Other Silicon Hydrides 77 Table 4.6
Page 85 and 86:
Silicon Hydride / Thiol Mixture 79
Page 87 and 88:
Silylated Cyclohexadienes 81 and (4
Page 89 and 90:
References 83 34. Kawashima, E., Uc
Page 91 and 92:
References 85 104. Gimisis, T., Bal
Page 93 and 94:
88 Addition to Unsaturated Bonds te
Page 95 and 96:
90 Addition to Unsaturated Bonds ap
Page 97 and 98:
92 Addition to Unsaturated Bonds 5.
Page 99 and 100:
94 Addition to Unsaturated Bonds R
Page 101 and 102:
96 Addition to Unsaturated Bonds Ph
Page 103 and 104:
98 Addition to Unsaturated Bonds EP
Page 105 and 106:
100 Addition to Unsaturated Bonds 5
Page 107 and 108:
102 Addition to Unsaturated Bonds T
Page 109 and 110:
104 Addition to Unsaturated Bonds R
Page 111 and 112:
106 Addition to Unsaturated Bonds a
Page 113 and 114:
Page 115 and 116:
110 Addition to Unsaturated Bonds S
Page 117 and 118:
112 Addition to Unsaturated Bonds T
Page 119 and 120:
114 Addition to Unsaturated Bonds I
Page 121 and 122:
Page 123 and 124:
Page 125 and 126:
120 Unimolecular Reactions 1 Si(H)M
Page 127 and 128:
122 Unimolecular Reactions t-Bu t-B
Page 129 and 130:
124 Unimolecular Reactions MeO Si O
Page 131 and 132:
126 Unimolecular Reactions t-Bu t-B
Page 133 and 134:
128 Unimolecular Reactions R 1 R 2
Page 135 and 136: 130 Unimolecular Reactions From the
Page 137 and 138: 132 Unimolecular Reactions rearrang
Page 139 and 140: 134 Unimolecular Reactions H 3 C +
Page 141 and 142: 136 Unimolecular Reactions Br O Si(
Page 143 and 144: 138 Unimolecular Reactions R3Si C C
Page 145 and 146: 140 Unimolecular Reactions Me3Si O
Page 147 and 148: 142 Unimolecular Reactions 43. Albe
Page 149 and 150: 144 Consecutive Radical Reactions c
Page 151 and 152: 146 Consecutive Radical Reactions O
Page 153 and 154: 148 Consecutive Radical Reactions a
Page 155 and 156: 150 Consecutive Radical Reactions d
Page 157 and 158: 152 Consecutive Radical Reactions T
Page 159 and 160: 154 Consecutive Radical Reactions M
Page 161 and 162: 156 Consecutive Radical Reactions F
Page 167 and 168: 162 Consecutive Radical Reactions i
Page 169 and 170: 164 Consecutive Radical Reactions A
Page 173 and 174: 168 Consecutive Radical Reactions r
Page 175 and 176: 170 Consecutive Radical Reactions E
Page 179 and 180: 174 Consecutive Radical Reactions A
Page 181 and 182: 176 Consecutive Radical Reactions P
Page 183 and 184: 178 Consecutive Radical Reactions f
Page 185: 180 Consecutive Radical Reactions O
Page 189 and 190: 184 Consecutive Radical Reactions 8
Page 191 and 192: 186 Silyl Radicals in Polymers and
Page 225 and 226: 220 List of Abbreviations PED photo
Page 227 and 228: 222 Index Carbonyl sulfide 111 Carb
Page 229 and 230: 224 Index Organosilicon boranes 2,
Page 231 and 232: 226 Index Triethylsilane as mediato
show all

"Front Matter". In: Organosilanes in Radical Chemistry - Index of

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

Delete template?

Save as template?