1 - Thieme: Science of Synthesis Knowledge Updates 2017/1 [Seite 1]
2 - Title Page [Seite 6]
3 - Copyright [Seite 8]
4 - Preface [Seite 9]
5 - Abstracts [Seite 11]
6 - Science of Synthesis Knowledge Updates 2017/1 [Seite 21]
7 - Table of Contents [Seite 23]
8 - 3.6.16 Gold-Catalyzed Cycloaddition Reactions [Seite 37]
8.1 - 3.6.16.1 Cycloadditions via Gold-Containing 1,n-Dipolar Intermediates [Seite 37]
8.1.1 - 3.6.16.1.1 Method 1: Gold-Containing Benzopyrylium Intermediates [Seite 38]
8.1.1.1 - 3.6.16.1.1.1 Variation 1: Gold-Containing Benzopyrylium Azomethine Ylides [Seite 44]
8.1.1.2 - 3.6.16.1.1.2 Variation 2: Gold-Containing 2-Oxoalkyl Oxonium Species [Seite 47]
8.1.2 - 3.6.16.1.2 Method 2: Furyl-Gold 1,n-Dipole Intermediates [Seite 48]
8.1.2.1 - 3.6.16.1.2.1 Variation 1: Furyl-Gold 1,3-Dipole Intermediates [Seite 48]
8.1.2.2 - 3.6.16.1.2.2 Variation 2: Furyl-Gold 1,4-Dipole Intermediates [Seite 51]
8.1.2.3 - 3.6.16.1.2.3 Variation 3: Furan-Based ortho-Quinodimethane Intermediates [Seite 54]
8.1.3 - 3.6.16.1.3 Method 3: Gold-Containing All-Carbon 1,3-Dipoles [Seite 55]
8.2 - 3.6.16.2 Cycloadditions via Gold-Coordinated Allene Intermediates [Seite 57]
8.2.1 - 3.6.16.2.1 Method 1: Cycloadditions Initiated by Gold Activation of Allenes [Seite 57]
8.2.2 - 3.6.16.2.2 Method 2: Cycloadditions Initiated by Gold Activation of Propargylic Carboxylates [Seite 69]
8.3 - 3.6.16.3 Cycloadditions via trans-Alkenylgold Intermediates [Seite 71]
8.3.1 - 3.6.16.3.1 Method 1: trans-Alkenylgold Intermediates Generated by Alkyne Activation [Seite 71]
8.3.1.1 - 3.6.16.3.1.1 Variation 1: Alkynes as Latent Alkenes in Gold-Catalyzed Cycloadditions [Seite 74]
8.4 - 3.6.16.4 Cycloadditions via Gold Carbene Intermediates [Seite 76]
8.4.1 - 3.6.16.4.1 Method 1: Gold Carbenes Generated by Cycloisomerization of Alkynes and Alkenes [Seite 76]
8.4.2 - 3.6.16.4.2 Method 2: Gold Carbenes Generated by 1,2-Acyloxy Migration of Propargyl Carboxylates [Seite 81]
8.4.3 - 3.6.16.4.3 Method 3: Gold Carbenes Generated by Alkyne Oxidation [Seite 84]
8.4.3.1 - 3.6.16.4.3.1 Variation 1: Gold-Catalyzed Cycloaddition Reactions by Nitrene Transfer [Seite 87]
8.4.3.2 - 3.6.16.4.3.2 Variation 2: Gold-Catalyzed Cycloaddition Reactions by Carbene Transfer [Seite 88]
8.4.4 - 3.6.16.4.4 Method 4: Gold Carbenes Generated by Diazo Decomposition [Seite 89]
8.5 - 3.6.16.5 Cycloadditions via Gold-Coordinated Heteroatom Intermediates [Seite 91]
9 - 4.4.7 Product Subclass 7: Silylboron Reagents [Seite 101]
9.1 - 4.4.7.1 Synthesis of Product Subclass 7 [Seite 104]
9.1.1 - 4.4.7.1.1 Preparation by Si-B Bond Formation [Seite 104]
9.1.1.1 - 4.4.7.1.1.1 Method 1: Nucleophilic Substitution at Boron with Silyllithium Reagents [Seite 104]
9.1.1.1.1 - 4.4.7.1.1.1.1 Variation 1: Substitution of Amino-Substituted Chloroboranes [Seite 104]
9.1.1.1.2 - 4.4.7.1.1.1.2 Variation 2: Substitution of a Diaryl-Substituted Fluoroborane [Seite 105]
9.1.1.1.3 - 4.4.7.1.1.1.3 Variation 3: Nucleophilic Substitution of Diol-Substituted Hydro- or Alkoxyboranes [Seite 106]
9.1.1.2 - 4.4.7.1.1.2 Method 2: Iridium-Catalyzed Borylation of Trialkylsilanes [Seite 107]
9.1.1.3 - 4.4.7.1.1.3 Method 3: Reductive Coupling of Chlorosilanes and Chloroboranes [Seite 108]
9.1.2 - 4.4.7.1.2 Modification of Si-B Substitution Pattern [Seite 109]
9.1.2.1 - 4.4.7.1.2.1 Method 1: Ligand Exchange at the Boron Atom [Seite 109]
9.1.2.2 - 4.4.7.1.2.2 Method 2: Manipulation at the Silicon Atom [Seite 111]
9.2 - 4.4.7.2 Applications of Product Subclass 7 in Organic Synthesis [Seite 113]
9.2.1 - 4.4.7.2.1 Method 1: Reactions with Alkynes [Seite 113]
9.2.1.1 - 4.4.7.2.1.1 Variation 1: Transition-Metal-Catalyzed Silaboration [Seite 113]
9.2.1.2 - 4.4.7.2.1.2 Variation 2: Palladium-Catalyzed Silaborative Cyclization [Seite 119]
9.2.1.3 - 4.4.7.2.1.3 Variation 3: Nickel-Catalyzed Silaborative Dimerization [Seite 120]
9.2.1.4 - 4.4.7.2.1.4 Variation 4: Palladium-Catalyzed (2 + 2 + 1) Cycloaddition with Silylenes [Seite 121]
9.2.1.5 - 4.4.7.2.1.5 Variation 5: Copper-Catalyzed Silylation [Seite 122]
9.2.2 - 4.4.7.2.2 Method 2: Reactions with Alkenes [Seite 127]
9.2.2.1 - 4.4.7.2.2.1 Variation 1: Platinum-Catalyzed Silaboration [Seite 127]
9.2.2.2 - 4.4.7.2.2.2 Variation 2: Base-Catalyzed Silaboration [Seite 131]
9.2.2.3 - 4.4.7.2.2.3 Variation 3: Photochemical Radical Silylation [Seite 132]
9.2.3 - 4.4.7.2.3 Method 3: Reactions with Conjugated Dienes and Enynes [Seite 133]
9.2.3.1 - 4.4.7.2.3.1 Variation 1: Transition-Metal-Catalyzed 1,4-Silaboration [Seite 133]
9.2.3.2 - 4.4.7.2.3.2 Variation 2: Platinum-Catalyzed Silaborative Coupling of 1,3-Dienes and Aldehydes [Seite 136]
9.2.3.3 - 4.4.7.2.3.3 Variation 3: Nickel-Catalyzed Silylative Coupling of 1,3-Dienes and Aldehydes [Seite 137]
9.2.3.4 - 4.4.7.2.3.4 Variation 4: Palladium-Catalyzed (4 + 1) Cycloaddition with Silylenes [Seite 138]
9.2.4 - 4.4.7.2.4 Method 4: Reactions with Allenes [Seite 140]
9.2.4.1 - 4.4.7.2.4.1 Variation 1: Palladium-Catalyzed Silaboration [Seite 140]
9.2.4.2 - 4.4.7.2.4.2 Variation 2: Copper-Catalyzed Silylation [Seite 145]
9.2.5 - 4.4.7.2.5 Method 5: Reactions with C=X Bonds [Seite 151]
9.2.5.1 - 4.4.7.2.5.1 Variation 1: 1,2-Silylation of Aldehydes [Seite 151]
9.2.5.2 - 4.4.7.2.5.2 Variation 2: 1,2-Silylation of Imines [Seite 153]
9.2.5.3 - 4.4.7.2.5.3 Variation 3: Reaction with Anhydrides [Seite 157]
9.2.6 - 4.4.7.2.6 Method 6: Reactions with ?,?-Unsaturated Carbonyl and Carboxy Compounds and Derivatives Thereof [Seite 158]
9.2.6.1 - 4.4.7.2.6.1 Variation 1: Transition-Metal-Catalyzed 1,4-Silylation of Enones and ?,?- Unsaturated Esters [Seite 158]
9.2.6.2 - 4.4.7.2.6.2 Variation 2: N-Heterocyclic Carbene Catalyzed 1,4-Silylation of Enones, Enals, or Unsaturated Esters [Seite 171]
9.2.6.3 - 4.4.7.2.6.3 Variation 3: Copper-Catalyzed 1,4-Silylation of Ynones and Derivatives Thereof [Seite 173]
9.2.6.4 - 4.4.7.2.6.4 Variation 4: Metal-Free Phosphine-Catalyzed Silaboration of Ynoates [Seite 178]
9.2.7 - 4.4.7.2.7 Method 7: Reactions with Allylic and Propargylic Electrophiles [Seite 179]
9.2.7.1 - 4.4.7.2.7.1 Variation 1: Copper-Catalyzed Allylic Substitution [Seite 179]
9.2.7.2 - 4.4.7.2.7.2 Variation 2: Silylative Cyclopropanation [Seite 184]
9.2.7.3 - 4.4.7.2.7.3 Variation 3: Transition-Metal-Catalyzed Propargylic Substitution [Seite 185]
9.2.8 - 4.4.7.2.8 Method 8: Reactions with (Het)arenes [Seite 187]
9.2.8.1 - 4.4.7.2.8.1 Variation 1: Silaborative Dearomatization of Nitrogen Heterocycles [Seite 187]
9.2.8.2 - 4.4.7.2.8.2 Variation 2: Nickel/Copper-Catalyzed Silylation [Seite 189]
9.2.8.3 - 4.4.7.2.8.3 Variation 3: Base-Catalyzed Borylation [Seite 191]
9.2.8.4 - 4.4.7.2.8.4 Variation 4: Iridium-Catalyzed Borylation [Seite 194]
9.2.9 - 4.4.7.2.9 Method 9: Reactions with Strained Ring Compounds [Seite 195]
9.2.9.1 - 4.4.7.2.9.1 Variation 1: Silaboration of Methylenecyclopropanes [Seite 195]
9.2.9.2 - 4.4.7.2.9.2 Variation 2: Silaboration of Vinylcyclopropanes, Vinylcyclobutanes, and Related Compounds [Seite 199]
9.2.10 - 4.4.7.2.10 Method 10: Reactions with Carbenoids and Related Compounds [Seite 201]
9.2.10.1 - 4.4.7.2.10.1 Variation 1: Insertion of Alkylidene-Type Carbenoids into the Si-B Bond [Seite 201]
9.2.10.2 - 4.4.7.2.10.2 Variation 2: Insertion of sp3-Carbon-Centered Carbenoids into the Si-B Bond [Seite 204]
9.2.10.3 - 4.4.7.2.10.3 Variation 3: Insertion of Isocyanides into the Si-B Bond [Seite 206]
9.2.11 - 4.4.7.2.11 Method 11: Miscellaneous Reactions [Seite 208]
9.2.11.1 - 4.4.7.2.11.1 Variation 1: Stereoselective Deoxygenation of trans-Stilbene Oxides [Seite 208]
9.2.11.2 - 4.4.7.2.11.2 Variation 2: B-N Bond Formation by Desilacoupling Catalyzed by a Strontium Bisamide Base [Seite 209]
10 - 4.4.11 Product Subclass 11: Silyllithium and Related Silyl Alkali Metal Reagents [Seite 213]
10.1 - 4.4.11.1 Method 1: Reductive Cleavage of Disilanes with Alkali Metals [Seite 214]
10.2 - 4.4.11.2 Method 2: Reduction of Halotriorganosilanes with Alkali Metals [Seite 215]
10.3 - 4.4.11.3 Method 3: Nucleophilic Cleavage of Si-M Bonds (M = Si, Sn, etc.) [Seite 216]
10.3.1 - 4.4.11.3.1 Variation 1: Si-Si Bond Cleavage [Seite 217]
10.3.2 - 4.4.11.3.2 Variation 2: Si-Sn Bond Cleavage [Seite 219]
10.4 - 4.4.11.4 Method 4: Si-H Bond Cleavage [Seite 219]
10.4.1 - 4.4.11.4.1 Variation 1: Si-H Bond Cleavage by Alkali Metals [Seite 219]
10.4.2 - 4.4.11.4.2 Variation 2: Si-H Bond Cleavage by Alkali Metal Hydrides [Seite 221]
10.5 - 4.4.11.5 Method 5: Preparation via Disilylmercury Compounds [Seite 222]
11 - 4.4.19.4 Silyl Sulfides and Selenides (Update 2017) [Seite 225]
11.1 - 4.4.19.4.1 Synthesis of Silyl Sulfides and Selenides [Seite 225]
11.1.1 - 4.4.19.4.1.1 Method 1: Synthesis by Reaction of Alkali Metals, Chalcogens, and Halosilanes or Alkali Metal Chalcogenides and Halosilanes [Seite 225]
11.1.1.1 - 4.4.19.4.1.1.1 Variation 1: From Lithium, Sulfur, and Halosilanes [Seite 225]
11.1.1.2 - 4.4.19.4.1.1.2 Variation 2: From Sodium, Sulfur, and Halosilanes [Seite 226]
11.1.1.3 - 4.4.19.4.1.1.3 Variation 3: From Lithium Sulfide and Halosilanes [Seite 227]
11.1.1.4 - 4.4.19.4.1.1.4 Variation 4: From Lithium Selenide and Halosilanes [Seite 228]
11.1.1.5 - 4.4.19.4.1.1.5 Variation 5: From Lithium Chalcogenides, Generated from Lithium Triethylborohydride and Chalcogens, and Halosilanes [Seite 229]
11.1.2 - 4.4.19.4.1.2 Method 2: Synthesis from Diselenides and Halosilanes [Seite 229]
11.1.2.1 - 4.4.19.4.1.2.1 Variation 1: From Dimethyl Diselenide, Lithium Aluminum Hydride, and Halosilanes [Seite 229]
11.1.2.2 - 4.4.19.4.1.2.2 Variation 2: From Diphenyl Diselenide, Sodium, and Halosilanes [Seite 230]
11.1.2.3 - 4.4.19.4.1.2.3 Variation 3: From Diphenyl Diselenide, Lithium in Liquid Ammonia, and Halosilanes [Seite 230]
11.1.3 - 4.4.19.4.1.3 Method 3: Synthesis from Selanols [Seite 231]
11.1.4 - 4.4.19.4.1.4 Method 4: Synthesis from Alkynes, Butyllithium, Sulfur, and Halosilanes [Seite 232]
11.1.5 - 4.4.19.4.1.5 Method 5: Synthesis Using Phosphorus-Based Reagents [Seite 233]
11.1.5.1 - 4.4.19.4.1.5.1 Variation 1: From Silylphosphines and Sulfur [Seite 233]
11.1.5.2 - 4.4.19.4.1.5.2 Variation 2: From Phosphine Sulfides and (Dimethylamino)trimethylsilane [Seite 233]
11.1.5.3 - 4.4.19.4.1.5.3 Variation 3: From Phosphorus Pentasulfide and Alkoxytrimethylsilanes or (Alkylsulfanyl)trimethylsilanes [Seite 234]
11.1.6 - 4.4.19.4.1.6 Method 6: Synthesis from Grignard Reagents, Selenium, and Halosilanes [Seite 234]
11.1.7 - 4.4.19.4.1.7 Method 7: Synthesis from Existing Silyl Selenides by Substitution of a Group on Selenium [Seite 235]
11.2 - 4.4.19.4.2 Applications of Silyl Sulfides and Selenides [Seite 235]
12 - 4.4.24.3 Silyl Cyanides (Update 2017) [Seite 239]
12.1 - 4.4.24.3.1 Tetracoordinate Silyl Cyanides [Seite 239]
12.1.1 - 4.4.24.3.1.1 Method 1: Transmetalation of Silyl Chlorides [Seite 239]
12.1.2 - 4.4.24.3.1.2 Method 2: Metathesis between Si-H and X-CN Bonds (X=C, N, O, Si) [Seite 240]
12.1.3 - 4.4.24.3.1.3 Method 3: Insertion of Silylenes into Isocyanides [Seite 241]
12.1.4 - 4.4.24.3.1.4 Method 4: Transformation of Si=C=N-Si Units [Seite 242]
12.2 - 4.4.24.3.2 Extracoordinate Silyl Cyanides [Seite 244]
12.2.1 - 4.4.24.3.2.1 Method 1: Reaction of Pentacoordinate Silyl Chlorides with Cyanotrimethylsilane [Seite 244]
12.2.2 - 4.4.24.3.2.2 Method 2: Reaction of Hexacoordinate Silyl Chlorides with Cyanotrimethylsilane [Seite 246]
13 - 4.4.47 Product Subclass 47: Silanols [Seite 249]
13.1 - 4.4.47.1 Synthesis of Silanols [Seite 249]
13.1.1 - 4.4.47.1.1 Method 1: Hydrolysis of Chlorosilanes [Seite 249]
13.1.1.1 - 4.4.47.1.1.1 Variation 1: Biphasic Hydrolysis of Chlorosilanes [Seite 250]
13.1.1.2 - 4.4.47.1.1.2 Variation 2: Biphasic Hydrolysis of Chlorosilanes with Triethylamine [Seite 250]
13.1.1.3 - 4.4.47.1.1.3 Variation 3: Synthesis of Bulky Silanediols from Chlorosilanes [Seite 251]
13.1.2 - 4.4.47.1.2 Method 2: Stoichiometric Oxidation of Silanes [Seite 252]
13.1.2.1 - 4.4.47.1.2.1 Variation 1: Oxidation of Silanes with Ozone [Seite 252]
13.1.2.2 - 4.4.47.1.2.2 Variation 2: Oxidation of Silanes with Peroxy Acids [Seite 253]
13.1.2.3 - 4.4.47.1.2.3 Variation 3: Oxidation of Silanes with Dioxiranes or Oxaziridines [Seite 254]
13.1.2.4 - 4.4.47.1.2.4 Variation 4: Oxidation of Silanes with Potassium Permanganate and Sonication [Seite 255]
13.1.2.5 - 4.4.47.1.2.5 Variation 5: Oxidation of Silanes with Osmium(VIII) Oxide [Seite 255]
13.1.3 - 4.4.47.1.3 Method 3: Catalytic Oxidation of Silanes [Seite 256]
13.1.3.1 - 4.4.47.1.3.1 Variation 1: Heterogeneous Catalytic Oxidation of Silanes with Water [Seite 257]
13.1.3.2 - 4.4.47.1.3.2 Variation 2: Catalytic Oxidation of Silanes with Nanoparticles [Seite 257]
13.1.3.3 - 4.4.47.1.3.3 Variation 3: Homogeneous Catalytic Oxidation of Silanes with Water [Seite 259]
13.1.3.4 - 4.4.47.1.3.4 Variation 4: Catalytic Oxidation of Silanes with Peroxides or Oxygen [Seite 264]
13.1.3.5 - 4.4.47.1.3.5 Variation 5: Organocatalytic Oxidation of Silanes [Seite 266]
13.1.4 - 4.4.47.1.4 Method 4: Hydrolysis of Aromatic C(sp2)-Si Bonds [Seite 266]
13.1.5 - 4.4.47.1.5 Method 5: Cleavage of Siloxy- and Alkoxysilanes [Seite 269]
13.2 - 4.4.47.2 Catalytic Activity of Silanols [Seite 271]
13.2.1 - 4.4.47.2.1 Method 1: Hydrogen-Bond-Donor Catalysis Involving Silanediols [Seite 271]
13.2.2 - 4.4.47.2.2 Method 2: Silanediols in Anion-Binding Catalysis [Seite 273]
13.2.3 - 4.4.47.2.3 Method 3: Catalytic Activity of Bissilanols [Seite 275]
13.2.4 - 4.4.47.2.4 Method 4: Catalytic Activity of Monosilanols [Seite 275]
13.3 - 4.4.47.3 Silanols as Directing Groups [Seite 277]
14 - 10.22.2 Product Subclass 2: Azaindol-1-ols [Seite 283]
14.1 - 10.22.2.1 Synthesis by Ring-Closure Reactions [Seite 283]
14.1.1 - 10.22.2.1.1 By Annulation to a Pyridine [Seite 283]
14.1.1.1 - 10.22.2.1.1.1 With Formation of One N-C Bond [Seite 283]
14.1.1.1.1 - 10.22.2.1.1.1.1 With Formation of the 1-2 Bond [Seite 283]
14.1.1.1.1.1 - 10.22.2.1.1.1.1.1 Method 1: From 2-(o-Nitropyridyl)acetates [Seite 283]
14.1.1.1.1.2 - 10.22.2.1.1.1.1.2 Method 2: From an (Alkenylpyridyl)hydroxylamine [Seite 285]
14.1.1.1.1.3 - 10.22.2.1.1.1.1.3 Method 3: From a 2-(3-Nitropyridin-2-yl)ethanone [Seite 286]
14.1.1.1.1.4 - 10.22.2.1.1.1.1.4 Method 4: From 2-(3-Nitropyridin-2-yl)pent-4-enenitrile [Seite 286]
14.1.1.1.2 - 10.22.2.1.1.1.2 With Formation of the 1-7a Bond [Seite 287]
14.1.1.1.2.1 - 10.22.2.1.1.1.2.1 Method 1: From 1-(3-Pyridyl)-2-nitropropene and an Isocyanide [Seite 287]
14.2 - 10.22.2.2 Synthesis by Substituent Modification [Seite 288]
14.2.1 - 10.22.2.2.1 Substitution of Existing Substituents [Seite 288]
14.2.1.1 - 10.22.2.2.1.1 Pyrrole Ring Substituents [Seite 288]
14.2.1.1.1 - 10.22.2.2.1.1.1 Method 1: Modification of C-Nitrogen at C2 [Seite 288]
14.2.1.1.2 - 10.22.2.2.1.1.2 Method 2: Modification of N-Oxygen at N1 [Seite 289]
15 - 10.22.3 Product Subclass 3: 1,3-Dihydroazaindol-2-ones [Seite 293]
15.1 - 10.22.3.1 Synthesis by Ring-Closure Reactions [Seite 293]
15.1.1 - 10.22.3.1.1 By Annulation to a Pyridine [Seite 293]
15.1.1.1 - 10.22.3.1.1.1 By Formation of Two N-C Bonds [Seite 293]
15.1.1.1.1 - 10.22.3.1.1.1.1 With Formation of the 1-7a and 1-2 Bonds [Seite 293]
15.1.1.1.1.1 - 10.22.3.1.1.1.1.1 Method 1: From 2-(2-Chloropyridin-3-yl)acetic Acid [Seite 293]
15.1.1.2 - 10.22.3.1.1.2 By Formation of One N-C Bond and One C-C Bond [Seite 294]
15.1.1.2.1 - 10.22.3.1.1.2.1 With Formation of the 1-2 and 2-3 Bonds [Seite 294]
15.1.1.2.1.1 - 10.22.3.1.1.2.1.1 Method 1: From Lithiated ortho-Methylpyridinamines [Seite 294]
15.1.1.2.2 - 10.22.3.1.1.2.2 With Formation of the 1-2 and 3-3a Bonds [Seite 295]
15.1.1.2.2.1 - 10.22.3.1.1.2.2.1 Method 1: From a 2-Pyridylhydrazide [Seite 295]
15.1.1.3 - 10.22.3.1.1.3 By Formation of Two C-C Bonds [Seite 296]
15.1.1.3.1 - 10.22.3.1.1.3.1 With Formation of 2-3 and 3-3a Bonds [Seite 296]
15.1.1.3.1.1 - 10.22.3.1.1.3.1.1 Method 1: From N-Pivaloylpyridinamines [Seite 296]
15.1.1.4 - 10.22.3.1.1.4 By Formation of One N-C Bond [Seite 297]
15.1.1.4.1 - 10.22.3.1.1.4.1 With Formation of the 1-7a Bond [Seite 297]
15.1.1.4.1.1 - 10.22.3.1.1.4.1.1 Method 1: From 2-(2-Chloropyridin-3-yl)acetamide [Seite 297]
15.1.1.4.1.2 - 10.22.3.1.1.4.1.2 Method 2: From 2-(2-Bromopyridin-3-yl)acetonitrile [Seite 298]
15.1.1.4.1.3 - 10.22.3.1.1.4.1.3 Method 3: From 2-Hydroxy-N-morpholino-2-(3-pyridyl)acetamide [Seite 298]
15.1.1.4.2 - 10.22.3.1.1.4.2 With Formation of the 1-2 Bond [Seite 300]
15.1.1.4.2.1 - 10.22.3.1.1.4.2.1 Method 1: From a 2-(Nitropyridyl)malonate [Seite 300]
15.1.1.4.2.2 - 10.22.3.1.1.4.2.2 Method 2: From a 2-Cyano-2-(3-nitropyridyl)acetate [Seite 303]
15.1.1.4.2.3 - 10.22.3.1.1.4.2.3 Method 3: From (3-Nitropyridyl)acetonitriles [Seite 307]
15.1.1.4.2.4 - 10.22.3.1.1.4.2.4 Method 4: From (3-Nitropyridyl)acetates [Seite 308]
15.1.1.4.2.5 - 10.22.3.1.1.4.2.5 Method 5: From (2-Aminopyridin-3-yl)acetic Acid [Seite 311]
15.1.1.5 - 10.22.3.1.1.5 By Formation of One C-C Bond [Seite 312]
15.1.1.5.1 - 10.22.3.1.1.5.1 With Formation of the 3-3a Bond [Seite 312]
15.1.1.5.1.1 - 10.22.3.1.1.5.1.1 Method 1: From N-(3-Bromopyridin-2-yl)alk-2-enamides [Seite 312]
15.1.1.5.1.2 - 10.22.3.1.1.5.1.2 Method 2: From N-Pyridylpropanamides [Seite 312]
15.1.1.5.1.3 - 10.22.3.1.1.5.1.3 Method 3: From N-(Halopyridyl) Amides [Seite 314]
15.1.1.5.1.4 - 10.22.3.1.1.5.1.4 Method 4: From N-(2-Chloropyridin-3-yl)acetamides [Seite 316]
15.1.1.5.1.5 - 10.22.3.1.1.5.1.5 Method 5: From a 2-Bromo-N-pyridylacetamide [Seite 316]
15.1.1.5.1.6 - 10.22.3.1.1.5.1.6 Method 6: From a Pyridylcarbamoylmethyl Xanthate [Seite 317]
15.1.1.5.1.7 - 10.22.3.1.1.5.1.7 Method 7: From Diethyl {2-[(2-Bromopyridin-3-yl)amino]- 2-oxoethyl}phosphonate and an Aldehyde [Seite 320]
15.2 - 10.22.3.2 Synthesis by Ring Transformation [Seite 321]
15.2.1 - 10.22.3.2.1 From Other Heterocyclic Systems [Seite 321]
15.2.1.1 - 10.22.3.2.1.1 Method 1: 1H-Pyrrolopyridines by 3,3-Dibromination [Seite 321]
15.2.1.2 - 10.22.3.2.1.2 Method 2: From a 1H-Pyrrolo[2,3-b]pyridine by Enzymatic Oxidation [Seite 326]
15.2.1.3 - 10.22.3.2.1.3 Method 3: From a 1H-Pyrrolopyridine-2,3-dione [Seite 326]
15.3 - 10.22.3.3 Synthesis by Substituent Modification [Seite 330]
15.3.1 - 10.22.3.3.1 Substitution of Existing Substituents [Seite 330]
15.3.1.1 - 10.22.3.3.1.1 Pyridine Ring Substituents [Seite 330]
15.3.1.1.1 - 10.22.3.3.1.1.1 Modification of C-Halogen at C5 [Seite 330]
15.3.1.1.1.1 - 10.22.3.3.1.1.1.1 Method 1: Formation of C-Carbon [Seite 330]
15.3.1.1.2 - 10.22.3.3.1.1.2 Modification of Nitrogen at N4 [Seite 333]
15.3.1.1.2.1 - 10.22.3.3.1.1.2.1 Method 1: Formation of N-Carbon [Seite 333]
15.3.1.2 - 10.22.3.3.1.2 Pyrrole Ring Substituents [Seite 334]
15.3.1.2.1 - 10.22.3.3.1.2.1 Substitution of C-Hydrogen at C3 [Seite 334]
15.3.1.2.1.1 - 10.22.3.3.1.2.1.1 Method 1: Formation of C-Carbon (Alkylation) [Seite 334]
15.3.1.2.1.2 - 10.22.3.3.1.2.1.2 Method 2: Formation of C-Carbon (Alkenylation) [Seite 339]
16 - 10.22.4 Product Subclass 4: 1,2-Dihydroazaindol-3-ones [Seite 349]
16.1 - 10.22.4.1 Synthesis by Ring-Closure Reactions [Seite 350]
16.1.1 - 10.22.4.1.1 By Annulation to a Pyridine [Seite 350]
16.1.1.1 - 10.22.4.1.1.1 By Formation of One N-C and One C-C Bond [Seite 350]
16.1.1.1.1 - 10.22.4.1.1.1.1 With Formation of the 1-7a and 2-3 Bonds [Seite 350]
16.1.1.1.1.1 - 10.22.4.1.1.1.1.1 Method 1: From a Pyridine Ester with an ortho-Amino Group [Seite 350]
16.1.1.1.2 - 10.22.4.1.1.1.2 With Formation of the 3-3a and 1-2 Bonds [Seite 351]
16.1.1.1.2.1 - 10.22.4.1.1.1.2.1 Method 1: From 3-Iodopyridin-2-amines and 1-Methoxyallene [Seite 351]
16.1.1.2 - 10.22.4.1.1.2 By Formation of One N-C Bond [Seite 352]
16.1.1.2.1 - 10.22.4.1.1.2.1 With Formation of the 1-7a Bond [Seite 352]
16.1.1.2.1.1 - 10.22.4.1.1.2.1.1 Method 1: From (2-Chloropyridin-3-yl)(1H-pyrrol-2-yl)methanone [Seite 352]
16.1.1.3 - 10.22.4.1.1.3 By Formation of One C-C Bond [Seite 352]
16.1.1.3.1 - 10.22.4.1.1.3.1 With Formation of the 2-3 Bond [Seite 352]
16.1.1.3.1.1 - 10.22.4.1.1.3.1.1 Method 1: From an N-Pyridylglycine [Seite 352]
16.1.2 - 10.22.4.1.2 By Annulation to a Pyrrole [Seite 354]
16.1.2.1 - 10.22.4.1.2.1 By Formation of Two C-C Bonds [Seite 354]
16.1.2.1.1 - 10.22.4.1.2.1.1 With Formation of the 4-5 and 6-7 Bonds [Seite 354]
16.1.2.1.1.1 - 10.22.4.1.2.1.1.1 Method 1: From a Masked 2-Amino-4-oxo-1H-pyrrole-3-carbaldehyde [Seite 354]
16.2 - 10.22.4.2 Synthesis by Ring Transformation [Seite 355]
16.2.1 - 10.22.4.2.1 From Other Heterocyclic Systems [Seite 355]
16.2.1.1 - 10.22.4.2.1.1 Method 1: From a Tetrazolo[1,5-a]pyridine [Seite 355]
16.2.1.2 - 10.22.4.2.1.2 Method 2: From a 1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde [Seite 355]
16.3 - 10.22.4.3 Synthesis by Substituent Modification [Seite 356]
16.3.1 - 10.22.4.3.1 Substitution of Existing Substituents [Seite 356]
16.3.1.1 - 10.22.4.3.1.1 Pyrrole Ring Substituents [Seite 356]
16.3.1.1.1 - 10.22.4.3.1.1.1 Modification of C-Oxygen at C3 [Seite 356]
16.3.1.1.1.1 - 10.22.4.3.1.1.1.1 Method 1: Formation of O-Carbon [Seite 356]
16.3.1.1.2 - 10.22.4.3.1.1.2 Substitution of C-Hydrogen at C2 [Seite 357]
16.3.1.1.2.1 - 10.22.4.3.1.1.2.1 Method 1: Formation of C-Carbon [Seite 357]
16.3.1.1.3 - 10.22.4.3.1.1.3 Modification of Nitrogen at N1 [Seite 359]
16.3.1.1.3.1 - 10.22.4.3.1.1.3.1 Method 1: Formation of N-Carbon [Seite 359]
17 - 10.22.5 Product Subclass 5: 1H-Azaindole-2,3-diones [Seite 361]
17.1 - 10.22.5.1 Synthesis by Ring-Closure Reactions [Seite 362]
17.1.1 - 10.22.5.1.1 By Annulation to a Pyridine [Seite 362]
17.1.1.1 - 10.22.5.1.1.1 By Formation of One N-C Bond [Seite 362]
17.1.1.1.1 - 10.22.5.1.1.1.1 With Formation of the 1-2 Bond [Seite 362]
17.1.1.1.1.1 - 10.22.5.1.1.1.1.1 Method 1: From {4-[(tert-Butoxycarbonyl)amino]pyridin-3-yl}glyoxylate [Seite 362]
17.2 - 10.22.5.2 Synthesis by Ring Transformation [Seite 362]
17.2.1 - 10.22.5.2.1 From Other Heterocyclic Systems [Seite 362]
17.2.1.1 - 10.22.5.2.1.1 Method 1: From a 1,3-Dihydro-2H-pyrrolopyridin-2-one [Seite 362]
17.2.1.2 - 10.22.5.2.1.2 Method 2: From a Pyrrolopyridine [Seite 365]
17.3 - 10.22.5.3 Synthesis by Substituent Modification [Seite 371]
17.3.1 - 10.22.5.3.1 Substitution of Existing Substituents [Seite 371]
17.3.1.1 - 10.22.5.3.1.1 Pyridine Ring Substituents [Seite 371]
17.3.1.1.1 - 10.22.5.3.1.1.1 Substitution of C-Hydrogen at C5 [Seite 371]
17.3.1.1.1.1 - 10.22.5.3.1.1.1.1 Method 1: Giving C-Halogen [Seite 371]
17.3.1.2 - 10.22.5.3.1.2 Pyrrole Ring Substituents [Seite 372]
17.3.1.2.1 - 10.22.5.3.1.2.1 Substitution of N-Hydrogen at N1 [Seite 372]
17.3.1.2.1.1 - 10.22.5.3.1.2.1.1 Method 1: Formation of N-Carbon [Seite 372]
18 - 10.22.6 Product Subclass 6: Azaindol-2- and Azaindol-3-amines [Seite 375]
18.1 - 10.22.6.1 Synthesis by Ring-Closure Reactions [Seite 375]
18.1.1 - 10.22.6.1.1 By Annulation to a Pyridine [Seite 375]
18.1.1.1 - 10.22.6.1.1.1 By Formation of One N-C and One C-C Bond [Seite 375]
18.1.1.1.1 - 10.22.6.1.1.1.1 With Formation of the 1-2 and 3-3a Bonds [Seite 375]
18.1.1.1.1.1 - 10.22.6.1.1.1.1.1 Method 1: From a 2-Halo-3-nitropyridine and a 2-Cyanoacetamide [Seite 375]
18.1.1.1.2 - 10.22.6.1.1.1.2 With Formation of the 1-2 and 2-3 Bonds [Seite 376]
18.1.1.1.2.1 - 10.22.6.1.1.1.2.1 Method 1: From Aminopyridine-3-carbonitriles [Seite 376]
18.1.1.2 - 10.22.6.1.1.2 By Formation of One N-C Bond [Seite 377]
18.1.1.2.1 - 10.22.6.1.1.2.1 With Formation of the 1-2 Bond [Seite 377]
18.1.1.2.1.1 - 10.22.6.1.1.2.1.1 Method 1: From an Ethyl 2-Cyano-2-(3-nitropyridyl)acetate [Seite 377]
18.1.1.2.1.2 - 10.22.6.1.1.2.1.2 Method 2: From a 2-[3-(Alkylamino)pyridin-2-yl]acetonitrile [Seite 378]
18.1.1.2.1.3 - 10.22.6.1.1.2.1.3 Method 3: From 3-Ethynyl-N-methylpyridin-2-amine [Seite 379]
18.1.1.3 - 10.22.6.1.1.3 By Formation of One C-C Bond [Seite 380]
18.1.1.3.1 - 10.22.6.1.1.3.1 With Formation of the 2-3 Bond [Seite 380]
18.1.1.3.1.1 - 10.22.6.1.1.3.1.1 Method 1: From Substituted 2-Aminopyridine-3-carbonitriles [Seite 380]
18.2 - 10.22.6.2 Synthesis by Ring Transformation [Seite 381]
18.2.1 - 10.22.6.2.1 From Other Heterocyclic Systems [Seite 381]
18.2.1.1 - 10.22.6.2.1.1 Method 1: From a Pyrrolopyridine [Seite 381]
18.2.1.1.1 - 10.22.6.2.1.1.1 Variation 1: From a Halopyrrolopyridine [Seite 381]
18.2.1.1.2 - 10.22.6.2.1.1.2 Variation 2: Via Nitrosation [Seite 382]
18.2.1.1.3 - 10.22.6.2.1.1.3 Variation 3: Via Diazonium Coupling [Seite 384]
18.2.1.1.4 - 10.22.6.2.1.1.4 Variation 4: By Reduction of Nitro Groups [Seite 385]
18.2.1.1.5 - 10.22.6.2.1.1.5 Variation 5: Via Azidation [Seite 388]
18.2.1.2 - 10.22.6.2.1.2 Method 2: From a 1,2,3-Dithiazole [Seite 390]
19 - 21.17 Synthesis of Amides (Including Peptides) in Continuous-Flow Reactors [Seite 393]
19.1 - 21.17.1 Microreactors: A Faster Tool for Synthesis Laboratories [Seite 394]
19.2 - 21.17.2 Amide Formation in Microflow Reactors: Exploring Different Possibilities [Seite 395]
19.2.1 - 21.17.2.1 Peptide Synthesis [Seite 395]
19.2.1.1 - 21.17.2.1.1 Method 1: Synthesis of Di- and Tripeptides in Solution [Seite 395]
19.2.1.2 - 21.17.2.1.2 Method 2: Synthesis of Di- and Tripeptides Using Immobilized Reagents [Seite 398]
19.2.1.3 - 21.17.2.1.3 Method 3: ?-Peptide Synthesis Using Fluorine-Activated Amino Acids [Seite 400]
19.2.1.4 - 21.17.2.1.4 Method 4: Peptide Synthesis Using Triphosgene as the Activating Agent [Seite 402]
19.2.1.5 - 21.17.2.1.5 Method 5: Cyclization of Peptides Driven by Microfluidics [Seite 405]
19.2.1.6 - 21.17.2.1.6 Method 6: Analysis of Racemization During Peptide Formation [Seite 407]
19.2.2 - 21.17.2.2 Synthesis of Drugs [Seite 407]
19.2.3 - 21.17.2.3 Carbonylation Reactions [Seite 409]
19.2.4 - 21.17.2.4 Lactam Synthesis [Seite 411]
19.2.5 - 21.17.2.5 Dendrimer Synthesis [Seite 411]
19.2.6 - 21.17.2.6 Miscellaneous Syntheses of Amides [Seite 413]
20 - 27.19.5 Azomethine Imines (Update 2017) [Seite 417]
20.1 - 27.19.5.1 Acyclic Azomethine Imines [Seite 417]
20.1.1 - 27.19.5.1.1 Synthesis and Applications of Acyclic Azomethine Imines [Seite 417]
20.1.1.1 - 27.19.5.1.1.1 Method 1: In Situ Generation from Hydrazones Followed by [3 +2] Cycloaddition [Seite 418]
20.1.1.1.1 - 27.19.5.1.1.1.1 Variation 1: In Situ Generation from Hydrazones with Boron Trifluoride- Diethyl Ether Complex and Subsequent Intramolecular [3+ 2] Cycloaddition [Seite 418]
20.1.1.1.2 - 27.19.5.1.1.1.2 Variation 2: In Situ Generation from Hydrazones with Iodosylbenzene and Subsequent [3 + 2] Cycloaddition with Imines [Seite 420]
20.1.1.2 - 27.19.5.1.1.2 Method 2: In Situ Generation from Aldehydes and Hydrazides [Seite 421]
20.1.1.2.1 - 27.19.5.1.1.2.1 Variation 1: In Situ Generation from Aldehydes and Hydrazides and Reaction with Nucleophiles [Seite 421]
20.1.1.2.2 - 27.19.5.1.1.2.2 Variation 2: In Situ Generation from Aldehydes and Hydrazides and Intermolecular [3 + 2] Cycloaddition with Alkynes [Seite 423]
20.2 - 27.19.5.2 Azomethine Imines with C-N Incorporated in a Ring [Seite 424]
20.2.1 - 27.19.5.2.1 Synthesis and Applications of Azomethine Imines with C-N Incorporated in a Ring [Seite 424]
20.2.1.1 - 27.19.5.2.1.1 Method 1: Synthesis of Cyclic Azomethine Imines from 2-(2-Bromoethyl)benzaldehydes and Benzoylhydrazine [Seite 424]
20.2.1.2 - 27.19.5.2.1.2 Method 2: Synthesis of Cyclic Azomethine Imines by Intramolecular Cyclization [Seite 426]
20.2.1.2.1 - 27.19.5.2.1.2.1 Variation 1: Synthesis of Cyclic Azomethine Imines from Alkynyl Hydrazides [Seite 426]
20.2.1.2.2 - 27.19.5.2.1.2.2 Variation 2: Synthesis of Cyclic Azomethine Imines from ?,?-Unsaturated N-Trichloroacetyl and N-Trifluoroacetyl Hydrazones [Seite 427]
20.2.1.3 - 27.19.5.2.1.3 Method 3: Synthesis of Cyclic Azomethine Imines from Pyridine Derivatives [Seite 428]
20.2.1.3.1 - 27.19.5.2.1.3.1 Variation 1: Synthesis of N-Benzoyl- and N-Tosyliminopyridinium Ylides from Pyridines by Amination and Acylation [Seite 428]
20.2.1.3.2 - 27.19.5.2.1.3.2 Variation 2: Synthesis of N-Tosyliminopyridinium Ylides from Pyridines by Metal-Catalyzed Imination with [N-(4-Toluenesulfonyl)imino]phenyliodinane [Seite 430]
20.2.1.4 - 27.19.5.2.1.4 Method 4: Metal-Catalyzed Synthesis of Cyclic Azomethine Imines from N?-(2-Alkynylbenzylidene) Hydrazides [Seite 431]
20.3 - 27.19.5.3 Azomethine Imines with N-N Incorporated in a Ring [Seite 433]
20.3.1 - 27.19.5.3.1 Synthesis and Applications of Azomethine Imines with N-N Incorporated in a Ring [Seite 433]
20.3.1.1 - 27.19.5.3.1.1 Method 1: Synthesis from Hydrazones and Alkenes [Seite 433]
21 - 35.1.5.1.12 Synthesis of 1-Chloro-n-Heteroatom-Functionalized Alkanes (n ?2) by Addition across C=C Bonds (Update 2017) [Seite 439]
21.1 - 35.1.5.1.12.1 Method 1: Dichlorination of Alkenes [Seite 439]
21.1.1 - 35.1.5.1.12.1.1 Variation 1: Using Manganese(III)/Hydrochloric Acid as the Chlorine Source [Seite 439]
21.1.2 - 35.1.5.1.12.1.2 Variation 2: Using an Iodine(III) Reagent as the Chlorine Source [Seite 441]
21.1.3 - 35.1.5.1.12.1.3 Variation 3: Using Organic Chlorides as the Chlorine Source [Seite 442]
21.1.4 - 35.1.5.1.12.1.4 Variation 4: Using Alkali Metal Chlorides as the Chlorine Source [Seite 445]
21.1.5 - 35.1.5.1.12.1.5 Variation 5: Using N-Chlorosuccinimide as the Chlorine Source [Seite 447]
21.1.6 - 35.1.5.1.12.1.6 Variation 6: Using a Carbene-Palladium(IV) Chloride Complex as the Chlorine Source [Seite 448]
21.1.7 - 35.1.5.1.12.1.7 Variation 7: Organocatalyzed Dichlorination of Alkenes [Seite 449]
21.2 - 35.1.5.1.12.2 Method 2: Aminochlorination of Alkenes [Seite 451]
21.2.1 - 35.1.5.1.12.2.1 Variation 1: Carbon Dioxide Promoted Aminochlorination of Alkenes Using Chloramine-Tas the Source of Chlorine and Nitrogen [Seite 452]
21.2.2 - 35.1.5.1.12.2.2 Variation 2: Transition-Metal-Catalyzed Aminochlorination of Alkenes [Seite 453]
21.2.3 - 35.1.5.1.12.2.3 Variation 3: Asymmetric Catalytic Aminochlorination of ?,?-Unsaturated ?-Oxo Esters [Seite 455]
21.2.4 - 35.1.5.1.12.2.4 Variation 4: Selenium-Catalyzed Chloroamidation of Alkenes [Seite 458]
21.2.5 - 35.1.5.1.12.2.5 Variation 5: Photocatalytic Aminochlorination of Alkenes [Seite 459]
21.3 - 35.1.5.1.12.3 Method 3: Halochlorination of Alkenes [Seite 460]
21.3.1 - 35.1.5.1.12.3.1 Variation 1: Iodochlorination of Styrene Using Tetramethylammonium Dichloroiodate [Seite 460]
21.3.2 - 35.1.5.1.12.3.2 Variation 2: Copper-Catalyzed Bromochlorination of Styrene Using Tetrabutylammonium Dichlorobromate [Seite 461]
21.3.3 - 35.1.5.1.12.3.3 Variation 3: Catalytic Enantioselective Bromochlorination of Allylic Alcohols [Seite 461]
21.4 - 35.1.5.1.12.4 Method 4: Oxychlorination of Alkenes [Seite 463]
21.4.1 - 35.1.5.1.12.4.1 Variation 1: Thiourea Catalyzed Methoxychlorination of Alkenes [Seite 463]
21.4.2 - 35.1.5.1.12.4.2 Variation 2: Iodine(III)-Mediated Methoxychlorination of Alkenes [Seite 464]
21.4.3 - 35.1.5.1.12.4.3 Variation 3: (Diacetoxyiodo)benzene-Mediated Ethoxychlorination of Enamides [Seite 465]
21.4.4 - 35.1.5.1.12.4.4 Variation 4: Organocatalytic Enantioselective Chlorocyclization of Unsaturated Amides [Seite 466]
21.5 - 35.1.5.1.12.5 Method 5: Chloroselanylation of Alkenes [Seite 468]
21.5.1 - 35.1.5.1.12.5.1 Variation 1: ?-Chloroselanylation of Alkenes with N,NDiethylbenzeneselenenamide in the Presence of Phosphoryl Chloride or Thionyl Chloride [Seite 468]
21.5.2 - 35.1.5.1.12.5.2 Variation 2: Chloroselanylation of Alkenes with Phenylselenenyl Chloride [Seite 469]
21.6 - 35.1.5.1.12.6 Method 6: Sulfanylchlorination of Alkenes [Seite 470]
21.7 - 35.1.5.1.12.7 Method 7: Trihalomethylchlorination of Alkenes [Seite 471]
21.7.1 - 35.1.5.1.12.7.1 Variation 1: Trichloromethylchlorination of Alkenes with Trichloromethanesulfonyl Chloride [Seite 471]
21.7.2 - 35.1.5.1.12.7.2 Variation 2: Trichloromethylchlorination of Alkenes in Subcritical Carbon Tetrachloride [Seite 472]
21.7.3 - 35.1.5.1.12.7.3 Variation 3: Copper/Ruthenium-Catalyzed Trifluoromethylchlorination of Alkenes [Seite 473]
21.8 - 35.1.5.1.12.8 Method 8: Azidochlorination of Alkenes [Seite 474]
21.8.1 - 35.1.5.1.12.8.1 Variation 1: Azidochlorination of Alkenes with Sodium Azide in the Presence of Sodium Hypochlorite and Acetic Acid [Seite 474]
21.9 - 35.1.5.1.12.9 Method 9: Chlorodiacetonylation of Alkenes [Seite 476]
21.9.1 - 35.1.5.1.12.9.1 Variation 1: Chlorodiacetonylation of Cycloalkenes with Acetylacetone and Manganese(III) Acetate in the Presence of Hydrochloric Acid [Seite 476]
22 - 35.2.1.5.7 Synthesis of Bromoalkanes by Substitution of Oxygen Functionalities (Update 2017) [Seite 479]
22.1 - 35.2.1.5.7.1 Method 1: Substitution of Alcoholic Hydroxy Groups [Seite 479]
22.1.1 - 35.2.1.5.7.1.1 Variation 1: Reaction of Alcohols with Oxalyl Chloride and Lithium Bromide under Catalysis by Triphenylphosphine Oxide [Seite 479]
22.1.2 - 35.2.1.5.7.1.2 Variation 2: Reaction of Alcohols with Diethyl Bromomalonate and Diphenylsilane under Catalysis of 5-Phenyldibenzophosphole [Seite 480]
22.1.3 - 35.2.1.5.7.1.3 Variation 3: Reaction of Primary Alcohols with 7,7-Dichlorocyclohepta- 1,3,5-triene and Tetrabutylammonium Bromide [Seite 481]
22.1.4 - 35.2.1.5.7.1.4 Variation 4: Reaction of Alcohols with 2,2-Dibromo- 1,3-dicyclohexylimidazolidine-4,5-dione [Seite 482]
22.1.5 - 35.2.1.5.7.1.5 Variation 5: Reaction of Alcohols with tert-Butyl Bromide in the Ionic Liquid 3-Methyl-1-pentylimidazolium Bromide [Seite 483]
22.2 - 35.2.1.5.7.2 Method 2: Cleavage of Silyl- and Tetrahydropyranyl-Protected Alcohols [Seite 484]
22.2.1 - 35.2.1.5.7.2.1 Variation 1: Reaction of Tetrahydropyranyl Ethers with Dibromotriphenylphosphorane [Seite 484]
22.2.2 - 35.2.1.5.7.2.2 Variation 2: Reaction of Tetrahydropyranyl and Silyl Ethers with N-Bromosaccharin-Triphenylphosphine [Seite 486]
22.2.3 - 35.2.1.5.7.2.3 Variation 3: Reaction of Tetrahydropyranyl and Silyl Ethers in Ionic Liquids [Seite 487]
22.3 - 35.2.1.5.7.3 Method 3: Substitution of Sulfonyloxy Groups [Seite 488]
22.3.1 - 35.2.1.5.7.3.1 Variation 1: Reaction of Arene- or Methanesulfonates with Lithium Bromide in Tetrahydrofuran [Seite 488]
22.3.2 - 35.2.1.5.7.3.2 Variation 2: Reaction of Methanesulfonates with Magnesium Bromide- Diethyl Ether Complex [Seite 489]
22.3.3 - 35.2.1.5.7.3.3 Variation 3: Reaction of Arene- or Methanesulfonates with the Ionic Liquid 1-Butyl-3-methylimidazolium Bromide [Seite 490]
23 - 35.2.2.2 Propargylic Bromides (Update 2017) [Seite 493]
23.1 - 35.2.2.2.1 Method 1: Synthesis by Heteroatom Substitution: Substitution of Hydroxy or Tetrahydropyranyl Ether Groups [Seite 493]
23.1.1 - 35.2.2.2.1.1 Variation 1: Reaction of Propargylic Alcohols with Phosphorus Tribromide in Perfluorohexane [Seite 494]
24 - 35.2.3.3.3 Synthesis of Benzylic Bromides by Substitution of ?-Bonded Heteroatoms (Update 2017) [Seite 497]
24.1 - 35.2.3.3.3.1 Method 1: Substitution of Oxygen Functionalities [Seite 497]
24.1.1 - 35.2.3.3.3.1.1 Variation 1: Reaction of (Hydroxymethyl)phenols with 2,4,6-Trichloro- 1,3,5-triazine and Sodium Bromide [Seite 500]
24.1.2 - 35.2.3.3.3.1.2 Variation 2: Reaction of Benzylic Alcohols with Poly(vinylpyrrolidin- 2-one)-Bromine Complex and Hexamethyldisilane [Seite 501]
24.1.3 - 35.2.3.3.3.1.3 Variation 3: Reaction of Benzylic Alcohols with Monolithic Triphenylphosphine Reagent and Carbon Tetrabromide [Seite 502]
25 - 35.2.4.2.3 Synthesis of Allylic Bromides by Substitution of ?-Bonded Heteroatoms (Update 2017) [Seite 505]
25.1 - 35.2.4.2.3.1 Method 1: Substitution of Other Halogens [Seite 505]
25.1.1 - 35.2.4.2.3.1.1 Variation 1: Reaction of Allylic Chlorides with 1,2-Dibromoethane under Rhodium Catalysis [Seite 505]
25.2 - 35.2.4.2.3.2 Method 2: Substitution of Hydroxy Groups [Seite 505]
26 - Author Index [Seite 509]
27 - Abbreviations [Seite 527]