| Preface |
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ix | |
| Glossary and Abbreviations |
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xi | |
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Organic Synthesis: General Remarks |
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1 | (16) |
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1 | (1) |
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2 | (7) |
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Convergent vs Linear Syntheses |
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2 | (1) |
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3 | (6) |
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Hard and Soft Acids and Bases |
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9 | (4) |
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The Curtin-Hammett Principle |
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13 | (4) |
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Stereoelectronic Effects and Reactivity |
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17 | (18) |
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Hyperconjugation with σ Bonds |
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17 | (2) |
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Hyperconjugation with Lone Electron Pairs |
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19 | (4) |
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19 | (1) |
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20 | (1) |
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Effects on Spectra and Structure |
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21 | (2) |
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Hyperconjugation and Reactivity |
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23 | (7) |
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Basicity and Nucleophilicity |
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23 | (2) |
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25 | (1) |
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26 | (1) |
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27 | (3) |
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30 | (5) |
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The Stability of Organic Compounds |
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35 | (24) |
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35 | (1) |
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35 | (6) |
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Incompatible Functional Groups |
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41 | (1) |
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Conjugation and Hyperconjugation of Incompatible Functional Groups |
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42 | (3) |
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45 | (7) |
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45 | (3) |
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48 | (3) |
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Addition of Oxygen to C--C Double Bonds |
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51 | (1) |
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52 | (7) |
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Aliphatic Nucleophilic Substitutions: Problematic Electrophiles |
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59 | (84) |
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Mechanisms of Nucleophilic Substitution |
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59 | (3) |
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Structure of the Leaving Group |
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62 | (10) |
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Good and Poor Leaving Groups |
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62 | (4) |
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Nucleophilic Substitution of Fluoride |
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66 | (4) |
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Nucleophilic Substitution of Sulfonates |
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70 | (2) |
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Structure of the Electrophile |
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72 | (71) |
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72 | (3) |
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75 | (4) |
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Electrophiles with σ-Heteroatoms |
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79 | (5) |
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Electrophiles with β-Heteroatoms |
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84 | (2) |
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Electrophiles with α-Electron-withdrawing Groups |
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86 | (4) |
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Neighboring-group Participation |
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90 | (3) |
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Allylic and Propargylic Electrophiles |
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93 | (4) |
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97 | (46) |
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The Alkylation of Carbanions |
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143 | (86) |
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143 | (1) |
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The Kinetics of Deprotonations |
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144 | (2) |
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Regioselectivity of Deprotonations and Alkylations |
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146 | (36) |
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146 | (2) |
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Kinetic/Thermodynamic Enolate Formation |
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148 | (2) |
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Allylic and Propargylic Carbanions |
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150 | (5) |
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Succinic Acid Derivatives and Amide-derived Carbanions |
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155 | (2) |
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157 | (1) |
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158 | (3) |
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161 | (10) |
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171 | (2) |
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Acyl, Imidoyl, and Related Carbanions |
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173 | (2) |
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175 | (5) |
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Aromatic vs Benzylic Deprotonation |
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180 | (2) |
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The Stability of Carbanions |
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182 | (47) |
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182 | (1) |
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183 | (1) |
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184 | (6) |
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190 | (3) |
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193 | (2) |
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195 | (1) |
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Other Factors which Influence the Stability of Carbanions |
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196 | (1) |
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Configurational Stability of Carbanions |
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197 | (32) |
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The Alkylation of Heteroatoms |
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229 | (32) |
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229 | (2) |
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Alkylation of Aliphatic Amines |
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231 | (3) |
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234 | (5) |
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239 | (2) |
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241 | (2) |
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243 | (5) |
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Alkylation of Carbamates and Ureas |
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248 | (2) |
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Alkylation of Amidines and Guanidines |
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250 | (1) |
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Alkylation of Carboxylates |
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251 | (10) |
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The Acylation of Heteroatoms |
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261 | (18) |
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Problematic Carboxylic Acids |
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261 | (6) |
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Sterically Demanding Carboxylic Acids |
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261 | (1) |
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Unprotected Amino and Hydroxy Carboxylic Acids |
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262 | (3) |
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Carboxylic Acids with Additional Electrophilic Groups |
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265 | (2) |
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267 | (4) |
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Sterically or Electronically Deactivated Amines |
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267 | (2) |
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269 | (1) |
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Amines with Additional Nucleophilic Groups |
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270 | (1) |
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271 | (8) |
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Sterically Deactivated and Base-labile Alcohols |
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271 | (2) |
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Alcohols with Additional Nucleophilic Groups |
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273 | (6) |
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Palladium-catalyzed C-C Bond Formation |
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279 | (30) |
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279 | (1) |
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Chemical Properties of Organopalladium Compounds |
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279 | (3) |
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Mechanisms of Pd-catalyzed C-C Bond Formation |
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282 | (5) |
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282 | (3) |
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285 | (2) |
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Homocoupling and Reduction of the Organyl Halide |
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287 | (4) |
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Homocoupling and Oxidation of the Carbon Nucleophile |
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291 | (2) |
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Transfer of Aryl Groups from the Phosphine Ligand |
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293 | (1) |
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ipso- vs cine-Substitution at Vinylboron and Vinyltin Derivatives |
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294 | (1) |
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Allylic Arylation and Hydrogenation as Side Reactions of the Heck Reaction |
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295 | (1) |
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Protodemetalation of the Carbon Nucleophile |
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296 | (1) |
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Sterically Hindered Substrates |
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296 | (2) |
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298 | (2) |
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300 | (9) |
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309 | (24) |
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309 | (1) |
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Baldwins Cyclization Rules |
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309 | (6) |
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Structural Features of the Chain |
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315 | (4) |
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319 | (8) |
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Formation of Cyclopropanes |
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321 | (4) |
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Formation of Cyclobutanes |
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325 | (2) |
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327 | (6) |
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Monofunctionalization of Symmetric Difunctional Substrates |
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333 | (22) |
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333 | (1) |
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Monofunctionalization of Dicarboxylic Acids |
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334 | (2) |
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Monofunctionalization of Diols |
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336 | (6) |
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Monofunctionalization of Diamines |
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342 | (4) |
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Monoalkylation of C,H-Acidic Compounds |
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346 | (2) |
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Monoderivatization of Dihalides |
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348 | (7) |
| Index |
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355 | |