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

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Index 223 Si w Si dissociation enthalpy 21 5–Hexenyl radical 32, 150 methyl substituted 150s 6–Hexenyl radical 151 Hinder amine light stabilizer (HALS) 197, 198 Homolytic substitution aromatic 90, 180 bimolecular (SH2) 61, 62s, 133 backside attack 133, 134 frontside attack 133, 134 intramolecular (SHi) 133, 134, 135, 136, 169, 187, 188 SHi reaction at silicon 134, 135, 136 ( )-Horsfiline 177 Hydride-affinity cycle 27 Hydrindanone 170 Hydrogenatomwithsiliconhydride 44,45t Hydrogen-terminated porous silicon photooxidation 205 preparation 203 Hydrogen-terminated Si(100) addition to monosubstituted olefin 213, 214s preparation 203, 213 Hydrogen-terminated Si(111) addition to aldehyde 210 addition to monosubstituted acetylene 210, 210f addition to monosubstituted olefin 208, 209, 209s, 210 comparison with tris(trimethylsilyl)silane 203, 206 FTIR spectrum 205, 205f halogenation 208 oxidation mechanism 106, 207s photooxidation 205 preparation 203 surface pattern 211, 211f, 212, 212f Hydrogen-terminated silicon surface 202, 203, 204, 204f Hydrosilylation of alkene 92–97 diastereoselectivity 93 enantioselectivity 95 radical-based mechanism 88 by silylated cyclohexadiene 97 stereoselectivity 93 thiol-promoted 95 transition metal catalysis 87 Hydrosilylation of alkyne 98, 99 Hydrosilylation of carbonyl compound 102–106 with PhSeSiMe3=Bu3SnH method 105, 106 stereoselectivity 103, 104 thiol-promoted 104 Hydrosilylation of enynes 159, 165 Intramolecular hydrosilylation alkenyloxysilane 121, 123, 125 carbon-carbon double bond 119–125 carbon-carbon triple bond 124–126 silylated cyclohexadiene 123, 124s thiol-promoted 121 Ion thermochemistry 25–28 Isogyric reaction 23 Isomerization cis/trans 90, 91f, 92, 99 Kinetic isotope effect 34, 37 ( )-Kumausallene 156 Lactam 58, 61, 148, 162, 166, 167, 168, 169 Lactone 145,160 Laser flash photolysis 40, 40t, 44, 44t, 51, 71, 73, 80, 97, 200, 202 Lewis acid complexation 159, 165 Macrocyclization 168, 176 Mucocin 157 Multiple scattering Xa 15 Narciclasine 171 Negative-ion cycle 26 Neophyl radical rearrangement 32, 172 Nitroxide 2, 41, 67, 68, 68s, 112, 113, 198 Nucleoside analogue 55, 56, 58, 60, 64, 65, 71, 171 Organic monolayer AFM image 212f derivatization 215 pattern by masking procedure 211, 211f, 212, 212f synthesis 209, 210, 213
224 Index Organosilicon boranes 2, 97 Oxauracil 162, 163 ( )-Pancracine 166 Pentamethyldisilane reducing agent 76 Si w H dissociation enthalpy 22t Pentamethyldisilyl radical addition to alkene 89, 89t addition to carbonyl compound 101 EPR spectrum 7 self-termination 51 with alkyl bromide 77t with alkyl chloride 77t Persistent radical 2, 9, 10, 10t, 109, 112, 121, 189 Phenylselenosilanes 3, 105, 106, 158, 158s Phenylsilane as mediator with alkyl bromide 153 dehydrocoupling polymerization 186 gas-phase acidity 27t gas-phase basicity 28t ionization potential 28 SiH dissociation enthalpy 27t Phenylsilyl radical electron affinity 27t ionization potential 28t Photoacoustic calorimetry 22 Photochemical addition to C60 cyclotetrasilane 201s, 202 disilacyclobutane 201s, 202 disilane 199 disilirane 201, 201s polysilane 200 Photochemical initiation 53, 57, 146, 147, 158, 166, 168, 178, 181, 199, 200, 201, 202, 206, 211, 212 Photoinduced electron transfer 3, 69, 158 Photolysis of silane 1, 2, 103, 137 Polarity-reversal catalysis 42, 79, 79s, 94 Poly(hexylhydrosilane) polydispersity index 195 with tert-butoxyl radical 188f, 189 Poly(hydrosilane) autoxidation 189, 190 dehydrogenative coupling of RSiH3 186 oxidizability value 189, 190 radical-based degradation 188 Poly(phenylhydrosilane) addition to carbonyl compound 197 addition to alkene 196 GPC analysis 187, 187f halogenation 195 oxidizability value 190 polydispersity index 187, 195 radical chain oxidation 191s reducing agent 195 with tert-butoxyl radical 187 Poly(phenylsilane), see also Poly(phenylhydrosilane) reducing agent 77 Polyhalogenated compound 70, 72, 73 Polysilane 185–198, 200 Polysiloxane 115 Polysilylene, see Polysilane Pyridinium replacement 67 Radical annulation 175, 176, 178, 181 Radical chain racemization 5, 42, 43s Radical clock methodology 32–38, 126, 195 Radical initiators 52–53 Radical translocation 34, 125, 180, 147s, 171, 180s, 196s, 206, 207s, 209, 209s, 214s Reduction, propagation step 50s Ring expansion 32, 35, 38, 126, 127, 152 Rydberg transition 16 Silacycloalkyl radical 5, 9, 120, 121, 122s Silicon hydride addition to carbonyl sulfide 111 gas-phase acidity 26, 27t gas-phase basicity 27, 28t oxidation to silanol 113,114 with phosphine sulfide 115 Silanethiol 80, 80s, 111, 115, 138 Silyl metal in one-electron oxidation 2 Silyl radical addition to alkene 88 addition to alkyne 97, 98 addition to benzene 90 addition to C60 199
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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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130 Unimolecular Reactions From the
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132 Unimolecular Reactions rearrang
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134 Unimolecular Reactions H 3 C +
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136 Unimolecular Reactions Br O Si(
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138 Unimolecular Reactions R3Si C C
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140 Unimolecular Reactions Me3Si O
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142 Unimolecular Reactions 43. Albe
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144 Consecutive Radical Reactions c
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146 Consecutive Radical Reactions O
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148 Consecutive Radical Reactions a
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150 Consecutive Radical Reactions d
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152 Consecutive Radical Reactions T
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154 Consecutive Radical Reactions M
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156 Consecutive Radical Reactions F
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162 Consecutive Radical Reactions i
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164 Consecutive Radical Reactions A
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168 Consecutive Radical Reactions r
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170 Consecutive Radical Reactions E
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Page 191 and 192: 186 Silyl Radicals in Polymers and
Page 225 and 226: 220 List of Abbreviations PED photo
Page 227: 222 Index Carbonyl sulfide 111 Carb
Page 231 and 232: 226 Index Triethylsilane as mediato
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