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

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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.
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Organosilanes in Radical Chemistry
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DEDICATION To my parents XrZstoB an
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viii Contents 3.6 Hydrogen Atom: An
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PREFACE A large number of papers de
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ACKNOWLEDGEMENTS I thank Keith U. I
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2 Formation and Structures of Silyl
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10 Formation and Structures of Sily
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2 Thermochemistry 2.1 GENERAL CONSI
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Bond Dissociation Enthalpies 21 Tab
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Bond Dissociation Enthalpies 23 2.2
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Ion Thermochemistry 25 Table 2.4 Re
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Ion Thermochemistry 27 Table 2.5 El
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References 29 3. Goumri, A., Yuan,
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32 Hydrogen Donor Abilities of Sili
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4 Reducing Agents 4.1 GENERAL ASPEC
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General Aspects of Radical Chain Re
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Tris(trimethylsilyl)silane 53 Therm
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Tris(trimethylsilyl)silane 55 4.3.1
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Tris(trimethylsilyl)silane 57 A goo
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Tris(trimethylsilyl)silane 59 C(O)C
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Tris(trimethylsilyl)silane 61 radic
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Tris(trimethylsilyl)silane 63 86% y
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Tris(trimethylsilyl)silane 65 RO RO
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Tris(trimethylsilyl)silane 67 O AcO
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Tris(trimethylsilyl)silane 69 Tris(
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Other Silicon Hydrides 71 The reduc
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Other Silicon Hydrides 73 The decre
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Other Silicon Hydrides 75 Ph MeS O
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Other Silicon Hydrides 77 Table 4.6
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Silicon Hydride / Thiol Mixture 79
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Silylated Cyclohexadienes 81 and (4
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References 83 34. Kawashima, E., Uc
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References 85 104. Gimisis, T., Bal
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88 Addition to Unsaturated Bonds te
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90 Addition to Unsaturated Bonds ap
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92 Addition to Unsaturated Bonds 5.
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94 Addition to Unsaturated Bonds R
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96 Addition to Unsaturated Bonds Ph
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98 Addition to Unsaturated Bonds EP
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100 Addition to Unsaturated Bonds 5
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102 Addition to Unsaturated Bonds T
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104 Addition to Unsaturated Bonds R
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106 Addition to Unsaturated Bonds a
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110 Addition to Unsaturated Bonds S
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112 Addition to Unsaturated Bonds T
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114 Addition to Unsaturated Bonds I
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120 Unimolecular Reactions 1 Si(H)M
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122 Unimolecular Reactions t-Bu t-B
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124 Unimolecular Reactions MeO Si O
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126 Unimolecular Reactions t-Bu t-B
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128 Unimolecular Reactions R 1 R 2
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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
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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
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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
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