Verfügbarkeit: Science of synthesis | Technische Universität München

Science of synthesis: Houben-Weyl methods of molecular transformations 35 = Category 5, Compounds with one saturated carbon-heteroatom bond Chlorine, bromine, and iodine

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Bibliographische Detailangaben
Beteilige Person:	Braun, M. (VerfasserIn)
Weitere beteiligte Personen:	Schaumann, Ernst 1943- (HerausgeberIn)
Format:	Buch
Sprache:	Englisch
Veröffentlicht:	Stuttgart [u.a.] Thieme 2007
Links:	http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=015420318&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA
Umfang:	XXXVIII, 850 Seiten Illustrationen 26 cm
ISBN:	9783131188717

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245	1	0	\|a Science of synthesis \|b Houben-Weyl methods of molecular transformations \|n 35 = Category 5, Compounds with one saturated carbon-heteroatom bond \|p Chlorine, bromine, and iodine \|c ed. board: D. Bellus ...
264		1	\|a Stuttgart [u.a.] \|b Thieme \|c 2007
300			\|a XXXVIII, 850 Seiten \|b Illustrationen \|c 26 cm
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Datensatz im Suchindex

DE-BY-TUM_call_number	0304 CHE 600b 03.2000 A 222-35
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adam_text	XV Table of Contents Introduction E. Schaumann Introduction 1 35.1 Product Class 1: One Saturated Carbon—Chlorine Bond 35.1.1 Product Subclass 1: Chloroalkanes E. Schaumann 35.1.1 Product Subclass 1: Chloroalkanes 15 35.1.1.1 Synthesis by Substitution of Hydrogen J. Hartung 35.1.1.1 Synthesis by Substitution of Hydrogen 19 35.1.1.1.1 Alkanes and Cycloalkanes 21 35.1.1.1.1.1 Method 1: Reactions with Molecular Chlorine 21 35.1.1.1.1.2 Method 2: Reactions with Sulfuryl Chloride 23 35.1.1.1.1.3 Method 3: Reactions with Trichloromethanesulfonyl Chloride 24 35.1.1.1.1.4 Method 4: Reactions with Trichloromethanesulfenyl Chloride 25 35.1.1.1.1.5 Method 5: Chlorination Reagents Containing an O—CI Bond 26 35.1.1.1.1.5.1 Variation 1: tert Butyl Hypochlorite as Chlorine Atom Donor 26 35.1.1.1.1.5.2 Variation 2: Chlorination with Chlorine Monoxide 26 35.1.1.1.1.6 Method 6: Reactions with Chloroamines 27 35.1.1.1.1.7 Method 7: Chlorination with Phosphorus Pentachloride 28 35.1.1.1.1.8 Method 8: Chlorination Reagents Containing an I—Cl Bond 28 35.1.1.1.1.8.1 Variation 1: (Dichloroiodo)benzene as Chlorine Atom Donor 28 35.1.1.1.1.8.2 Variation 2: Iodine Trichloride as Chlorine Atom Donor 29 35.1.1.1.1.9 Method 9: Chlorination with Carbon Tetrachloride in the Presence of Transition Metal Carbonyl Complexes 29 35.1.1.1.2 Haloalkanes and Halocycloalkanes 30 35.1.1.1.2.1 Method 1: Reactions with Molecular Chlorine 30 35.1.1.1.3 Alcohols 31 35.1.1.1.3.1 Method 1: Reactions with Molecular Chlorine 31 35.1.1.1.3.2 Method 2: Reactions with Chloroamines 32 35.1.1.1.4 Ethers 32 35.1.1.1.4.1 Method 1: Reactions with Molecular Chlorine 32 35.1.1.1.4.2 Method 2: Reactions with Hypohalites 34 35.1.1.1.4.3 Method 3: Chlorination with (Dichloroiodo)arenes 35 XVI Table of Contents 35.1.1.1.4.4 Method 4: Reactions with Phosphorus Pentachloride 36 35.1.1.1.5 Aldehydes 36 35.1.1.1.5.1 Method 1: Reactions with Sulfuryl Chloride 36 35.1.1.1.5.2 Method 2: Reactions with N Chlorosuccinimide 37 35.1.1.1.6 Ketones 37 35.1.1.1.6.1 Method 1: Reactions with Molecular Chlorine 37 35.1.1.1.6.2 Method 2: Reactions with Manganese(lll) Acetate and Lithium Chloride 38 35.1.1.1.6.3 Method 3: Chlorination with Sulfuryl Chloride 39 35.1.1.1.7 Carboxylic Acids and Derivatives 39 35.1.1.1.7.1 Method 1: Reactions with Molecular Chlorine 39 35.1.1.1.7.2 Method 2: Reactions with Sulfuryl Chloride 41 35.1.1.U.3 Method 3: Reactions with Chloroamines 42 35.1.1.1.8 Amines 43 35.1.1.1.8.1 Method 1: Reactions with Molecular Chlorine 43 35.1.1.2 Synthesis by Substitution of Metals P. Margaretha 35.1.1.2 Synthesis by Substitution of Metals 47 35.1.1.2.1 Method 1: Synthesis from Organo Croup 15 Derivatives 47 35.1.1.2.2 Method 2: Synthesis from Trialkylboranes 47 35.1.1.3 Synthesis by Substitution of Carbon Functionalities P. Margaretha 35.1.1.3 Synthesis by Substitution of Carbon Functionalities 49 35.1.1.3.1 Method 1: Decarbonylation of Acyl Chlorides 49 35.1.1.3.2 Method 2: Chlorodecarboxylation of the Heavy Metal Salts of Carboxylic Acids 49 35.1.1.3.3 Method 3: Chlorodecarboxylation of Carboxylic Acids by Lead(IV) Acetate 50 35.1.1.3.3.1 Variation 1: Chlorodecarboxylation in the Presence of Lithium Chloride ¦•• 51 35.1.1.3.3.2 Variation 2: Chlorodecarboxylation in the Presence of N Chlorosuccinimide 52 35.1.1.3.4 Method 4: Chlorodecarboxylation of 1 (Acyloxy)pyridine 2(1H) thiones •• 53 35.1.1.4 Synthesis by Substitution of Other Halogens P. Margaretha 35.1.1.4 Synthesis by Substitution of Other Halogens 59 35.1.1.4.1 Method 1: Substitution of Bromine 59 35.1.1.4.2 Method 2: Substitution of Bromine or Iodine 60 Table of Contents XVII 35.1.1 5 Synthesis by Substitution of Oxygen Functionalities P. Margaretha 35.1.15 Synthesis by Substitution of Oxygen Functionalities 63 35.1.1.5.1 Method 1: Decarboxylation of Chloroformates 63 35.1.1.5.2 Method 2: Synthesis from Alkanesulfonates and a Source of Chloride Ion 64 35.1.1.5.2.1 Variation 1: Using Lithium Chloride 64 35.1.1.5.2.2 Variation 2: Using Sodium or Potassium Chloride 65 35.1.1.5.2.3 Variation 3: Using Calcium Chloride 65 35.1.1.5.2.4 Variation 4: Using Pyridinium Hydrochloride 66 35.1.1.5.2.5 Variation 5: Using Tetraalkylammonium Chlorides 66 35.1.1.5.3 Method 3: Synthesis from Alkyl Xanthates (O Alkyldithiocarbonates) or from Thionocarbonates (O,0 Dialkylthiocarbonates) 67 35.1.1.5.4 Method 4: Replacement of an Alcoholic Hydroxy Croup with Hydrogen Chloride or a Metal Halide 68 35.1.1.5.4.1 Variation 1: Using Hydrochloric Acid or Hydrogen Chloride 68 35.1.1.5.4.2 Variation 2: Using Sodium Chloride 69 35.1.1.5.4.3 Variation 3: Using Tin(IV) Chloride 70 35.1.1.5.5 Method 5: Replacement of an Alcoholic Hydroxy Group with Thionyl Chloride 70 35.1.1.5.5.1 Variation 1: In an Inert Solvent in the Absence of a Base 71 35.1.1.5.5.2 Variation 2: In the Absence of a Solvent 72 35.1.1.5.5.3 Variation 3: In the Presence of an Equimolar Amount of Pyridine 72 35.1.1.5.5.4 Variation 4: In the Presence of an Equimolar Amount of IH Benzotriazole 73 35.1.1.5.5.5 Variation 5: In the Presence of Excess Triethylamine 74 35.1.1.5.6 Method 6: Replacement of an Alcoholic Hydroxy Croup with Selenium Tetrachloride 75 35.1.1.5.7 Method 7: Replacement of an Alcoholic Hydroxy Group with Chlorides of Phosphoric Acid and Related Compounds 76 35.1.1.5.7.1 Variation 1: Using Phosphorus Pentachloride 76 35.1.1.5.7.2 Variation 2: Using Phosphoryl Chloride 77 35.1.1.5.8 Method 8: Replacement of an Alcoholic Hydroxy Group via Oxyphosphonium Intermediates 78 35.1.1.5.8.1 Variation 1: Using Triphenylphosphine and Tetrachloromethane 79 35.1.1.5.8.2 Variation 2: Using Triphenylphosphine/2,3 Dichloro 5,6 dicyanobenzo 1,4 quinone and a Quaternary Ammonium Chloride 81 35.1.1.5.8.3 Variation 3: Using Triphenylphosphine and Cyclic N Chloroimides 82 35.1.1.5.8.4 Variation 4: Using Triphenylphosphine and Dichloroselenuranes 83 35.1.1.5.8.5 Variation 5: Using Triphenylphosphine, Diethyl Azodicarboxylate, and Zinc(ll) Chloride 84 35.1.1.5.9 Method 9: Replacement of an Alcoholic Hydroxy Group with Acetyl Chloride 84 35.1.1.5.10 Method 10: Replacement of an Alcoholic Hydroxy Group with Chloro methylenedimethyliminium Chloride and Related Reagents 85 35.1.1.5.11 Method 11: Replacement of an Alcoholic Hydroxy Group with tert Butyl Chloride in an Ionic Liquid 90 XVIII Table of Contents 35.1.1.5.12 Method 12: Replacement of an Alcoholic Hydroxy Croup with Chlorotrimethylsilane 90 35.1.1.5.12.1 Variation 1: In the Absence of Catalyst 90 35.1.1.5.12.2 Variation 2: In the Presence of Selenium Dioxide 91 35.1.1.5.12.3 Variation 3: In the Presence of Dimethyl Sulfoxide 91 35.1.1.5.12.4 Variation 4: In the Presence of Bismuth(lll) Chloride 92 35.1.1.6 Synthesis by Substitution of Sulfur, Selenium, or Tellurium Functionalities P. Margaretha 35.1.1.6 Synthesis by Substitution of Sulfur, Selenium, or Tellurium Functionalities 95 35.1.1.6.1 Method 1: Chloroalkanes from Alkyl Phenyl Tellurides 95 35.1.1.7 Synthesis by Substitution of Nitrogen Functionalities P. Margaretha 35.1.1.7 Synthesis by Substitution of Nitrogen Functionalities 99 35.1.1.7.1 Method 1: Synthesis from Primary Aliphatic Amines 99 35.1.1.7.2 Method 2: Synthesis from Tertiary Aliphatic Amines 99 35.1.1.7.3 Method 3: Synthesis from N Alkyl Substituted Amides 100 35.1.1.7.4 Method 4: Synthesis from N Alkyl N tosylhydrazines 100 35.1.1.8 Synthesis by Addition to n Type C—C Bonds K. M. Roy 35.1.1.8 Synthesis by Addition to rr Type C—C Bonds 103 35.1.1.8.1 Method 1: Hydrochlorination of Alkynes or Allenes 103 35.1.1.8.1.1 Variation 1: Preparation of 4 Chlorobuta 1,2 diene from But 1 en 3 yne 103 35.1.1.8.2 Method 2: Hydrochlorination of Polyenes 104 35.1.1.8.2.1 Variation 1: Conversion of Natural and Synthetic Rubbers 104 35.1.1.8.3 Method 3: Hydrochlorination of 1,3 Dienes 104 35.1.1.8.3.1 Variation 1: Using Hydrogen Chloride 104 35.1.1.8.3.2 Variation 2: Synthesis of 1 Chloro 3 methylbut 2 ene Using Thionyl Chloride/Silica Gel 105 35.1.1.8.4 Method 4: Hydrochlorination of Symmetrical Alkenes and Cycloalkenes 106 35.1.1.8.5 Method 5: Hydrochlorination of Unsymmetrical Alkenes and Cycloalkenes (Markovnikov Addition) 106 35.1.1.8.5.1 Variation 1: Synthesis with Aqueous Hydrogen Chloride 107 35.1.1.8.5.2 Variation 2: Synthesis under Phase Transfer Conditions 108 35.1.1.8.5.3 Variation 3: Synthesis Using an Inorganic Support 108 35.1.1.8.6 Method 6: Hydrochlorination of Unsymmetrical Alkenes and Cycloalkenes (anti Markovnikov Addition) 108 35.1.1.8.6.1 Variation 1: Synthesis via Hydroboration 109 35.1.1.8.6.2 Variation 2: Synthesis via Hydroalumination 110 35.1.1.8.7 Method 7: Enantioselective Hydrochlorination Reactions 110 35.1.1.8.8 Method 8: Hydrochlorination of Methylenecyclopropanes 111 Table of Contents XIX 35.1.1.8.8.1 Variation 1: Synthesis with Hydrogen Chloride 111 35.1.1.8.8.2 Variation 2: Synthesis with Metal Chlorides 112 35.1.1.8.9 Method 9: Hydrochlorination of Cyclopropanes 112 35.1.1.8.10 Method 10: Carbochlorination 113 35.1.1.9 Synthesis from Other Chlorine Compounds H. Ulrich 35.1.1.9 Synthesis from Other Chlorine Compounds 117 35.1.1.9.1 Method 1: Synthesis from Chloroalkynes by Hydrogenation 117 35.1.1.9.2 Method 2: Synthesis from Chloroalkenes 117 35.1.1.9.2.1 Variation 1: By Hydrogenation 117 35.1.1.9.2.2 Variation 2: By Polymerization 118 35.1.1.9.2.3 Variation 3: Coupling Reactions 120 35.1.1.9.2.4 Variation 4: [2+ 2] Cycloaddition Reactions 120 35.1.1.9.2.5 Variation 5: [2+ 3] Cycloaddition Reactions 125 35.1.1.9.2.6 Variation 6: [2+4] Cycloaddition Reactions 126 35.1.1.9.3 Method 3: Synthesis from Chlorocarbenes 127 35.1.1.9.4 Method 4: Synthesis from Chloroalkanes 129 35.1.1.9.4.1 Variation 1: By Insertion of Methylene into C CI Bonds 129 35.1.1.9.4.2 Variation 2: Chloroalkylation Reactions 129 35.1.1.9.4.3 Variation 3: By Isomerization Reactions 130 35.1.1.9.4.4 Variation 4: Elimination of Benzeneseleninic Acid 130 35.1.2 Product Subclass 2: Propargylic Chlorides P. Margaretha 35.1.2 Product Subclass 2: Propargylic Chlorides 133 35.1.2.1 Synthesis by Heteroatom Substitution 133 35.1.2.1.1 Synthesis by Deoxidative Halogenation of Ketones 133 35.1.2.1.1.1 Method 1: Addition of Chlorodimethylsilane to Ketones 133 35.1.2.1.2 Synthesis by Substitution of o Bonded Heteroatoms 134 35.1.2.1.2.1 Method 1: Synthesis from Propargylic Alcohols and Hydrochloric Acid 134 35.1.2.1.2.1.1 Variation 1: Chlorination Using Hydrochloric Acid, Calcium Chloride, Copper(l) Chloride, and Copper Metal 134 35.1.2.1.2.1.2 Variation 2: Chlorination Using Gaseous Hydrogen Chloride 135 35.1.2.1.2.2 Method 2: Synthesis from Propargylic Alcohols and Thionyl Chloride ¦ ¦ ¦ 136 35.1.2.1.2.3 Method 3: Synthesis from Propargylic Alcohols and 1 Chloro N,/V,2 trimethylprop 1 en 1 amine 136 XX Table of Contents 35.1.3 Product Subclass 3: Benzylic Chlorides 35.1.3.1 Synthesis by Substitution of Hydrogen W. D. Pfeiffer 35.1.3.1 Synthesis by Substitution of Hydrogen 139 35.1.3.1.1 Method 1: Reaction with Chlorine under Irradiation 139 35.1.3.1.2 Method 2: Reaction with Chlorine and a Catalyst 141 35.1.3.1.3 Method 3: Reaction with Liquid Chlorine 142 35.1.3.1.4 Method 4: Reaction with Benzyltrimethylammonium Tetrachloroiodate 143 35.1.3.1.5 Method 5: Reaction with tert Butyl Hypochlorite 144 35.1.3.1.6 Method 6: Reaction with Sulfuryl Chloride and a Catalyst 144 35.1.3.1.7 Method 7: Reaction with Benzenesulfonyl Chloride 146 35.1.3.1.8 Method 8: Reaction with Trichloromethanesulfonyl Chloride 147 35.1.3.1.9 Method 9: Reaction with N Chlorosuccinimide 147 35.1.3.1.10 Method 10: Reaction with 1,3,5 Trichloro 1,3,5 triazine 2,4,6(1H,3H,5H) trione (Trichloroisocyanuric Acid) 149 35.1.3.1.11 Method 11: Reaction with Ammonium Cerium(IV) Nitrate Lithium Chloride or Cobalt(lll) Acetate Lithium Chloride 149 35.1.3.1.12 Method 12: Reaction with Phosphorus Pentachloride 150 35.1.3.1.13 Method 13: Reaction with Phosphoryl Chloride 151 35.1.3.1.14 Method 14: Reaction with Trichloroacetyl Chloride, Chloroacetyl Chloride, Benzoyl Chloride, or Ethyl Chloroformate 151 35.1.3.1.15 Method 15: Reaction with Trichloromethyl Chloroformate or Bis(trichloromethyl) Carbonate 152 35.1.3.2 Synthesis by Substitution of Carbonyl Oxygen W. D. Pfeiffer 35.1.3.2 Synthesis by Substitution of Carbonyl Oxygen 155 35.1.3.2.1 Method 1: Chloroalkylation with Aldehydes 155 35.1.3.2.1.1 Variation 1: Chloromethylation with Paraformaldehyde and Hydrogen Chloride 155 35.1.3.2.1.2 Variation 2: Chloromethylation with Formaldehyde and Hydrogen Chloride 158 35.1.3.2.1.3 Variation 3: Chloromethylation with 1,3,5 Trioxane 159 35.1.3.2.1.4 Variation 4: Chloroalkylation with Acetaldehyde 159 35.1.3.2.2 Method 2: Chloromethylation with Chloromethyl Methyl Ether or Bis(chloromethyl) Ether 160 35.1.3.2.3 Method 3: Chloromethylation with Methoxyacetyl Chloride and Aluminum Trichloride 161 35.1.3.2.4 Method 4: Chloromethylation with 1 Chloro 4 (chloromethoxy)butane or 1,4 Bis(chloromethoxy)butane 162 35.1.3.2.5 Method 5: Chloroalkylation of Arenecarbaldehydes Using Alkylboron Dichlorides in the Presence of Oxygen 162 Table of Contents XXI 35.1.3.3 Synthesis by Substitution of o Bonded Heteroatoms P. Margaretha 35.1.3.3 Synthesis by Substitution of o Bonded Heteroatoms 167 35.1.3.3.1 Benzylic Chlorides from Other Benzylic Halides 167 35.1.3.3.1.1 Method 1: Benzylic Chlorides from Benzylic Bromides Using Tin(IV) Chloride 167 35.1.3.3.2 Benzylic Chlorides from Benzylic Alcohols 167 35.1.3.3.2.1 Method 1: Synthesis Using Thionyl Chloride 168 35.1.3.3.2.2 Method 2: Synthesis Using 4 Toluenesulfonyl Chloride 168 35.1.3.3.2.3 Method 3: Synthesis Using Carbon Tetrachloride 169 35.1.3.3.2.4 Method 4: Synthesis Using Silica Chloride 169 35.1.3.3.2.5 Method 5: Synthesis Using Chlorotrimethylsilane 170 35.1.3.3.2.5.1 Variation 1: With Tellurium Dioxide 170 35.1.3.3.2.5.2 Variation 2: With Dimethyl Sulfoxide 171 35.1.3.3.3 Benzylic Chlorides from Benzylic Ethers 171 35.1.3.3.3.1 Method 1: Cleavage with Zinc and Acetyl Chloride 171 35.1.4 Product Subclass 4: Allylic Chlorides 35.1.4.1 Synthesis by Substitution of Hydrogen a to a C=C Bond W. D. Pfeiffer 35.1.4.1 Synthesis by Substitution of Hydrogen a to a C=C Bond 173 35.1.4.1.1 Method 1: Reaction with Chlorine 173 35.1.4.1.2 Method 2: Reaction with Hypochlorous Acid 174 35.1.4.1.3 Method 3: Reaction with Chlorine Monoxide 175 35.1.4.1.4 Method 4: Reaction with tert Butyl Hypochlorite 176 35.1.4.1.5 Method 5: Reaction with N Chloro A/ cyclohexylbenzenesulfonamide ••• 177 35.1.4.1.6 Method 6: Reaction with N Chlorosuccinimide 177 35.1.4.1.7 Method 7: Reaction with a Vilsmeier Reagent and Hydrogen Peroxide •¦ 178 35.1.4.1.8 Method 8: Synthesis by Electrochemical Chlorination 179 35.1.4.2 Synthesis by Substitution of o Bonded Heteroatoms P. Margaretha 35.1.4.2 Synthesis by Substitution of o Bonded Heteroatoms 181 35.1.4.2.1 Methodi: Allylic Chlorides from Other Allylic Halides 181 35.1.4.2.2 Method 2: Allylic Chlorides from Allylic Alcohols 181 35.1.4.2.2.1 Variation 1: With Thionyl Chloride 182 35.1.4.2.2.2 Variation 2: With Methanesulfonyl Chloride 182 35.1.4.2.2.3 Variation 3: With N Chlorosuccinimide and Dimethyl Sulfide 183 XXII Table of Contents 35.1.4.2.2.4 Variation 4: With Carbon Tetrachloride or Hexachloroacetone and Triphenylphosphine 183 35.1.4.2.2.5 Variation 5: With 1 Chloro N,N,2 trimethylprop 1 enylamine 185 35.1.4.2.2.6 Variation 6: With Chlorotrimethylsilane in the Presence of Bismuth(lll) Chloride 186 35.1.4.2.2.7 Variation 7: Allylic Chlorides from Allylic Phosphates 186 35.1.4.2.3 Method 3: Allylic Chlorides from Allyloxybenzenes 187 35.1.S Product Subclass 5:1 Chloro n Heteroatom Functionalized Alkanes (n 2) with Both Functions Formed Simultaneously 35.1.S.1 Synthesis by Addition across C=C Bonds R. Cottlich 35.1.5.1 Synthesis by Addition across C=C Bonds 189 35.1.5.1.1 Method 1: Chlorination of Arenes 189 35.1.5.1.2 Method 2: Chlorination of Alkenes 192 35.1.5.1.2.1 Variation 1: Using Chlorine 192 35.1.5.1.2.2 Variation 2: Using Sulfuryl Chloride 198 35.1.5.1.2.3 Variation 3: Using Other Reagents 200 35.1.5.1.3 Method 3: Bromochlorination of Alkenes ••• 203 35.1.5.1.4 Method 4: lodochlorination of Alkenes 206 35.1.5.1.5 Method 5: Fluorochlorination of Alkenes 208 35.1.5.1.6 Method 6: Oxychlorination of Alkenes 210 35.1.5.1.6.1 Variation 1: Intermolecular Addition 210 35.1.5.1.6.2 Variation 2: Intramolecular Cyclization 215 35.1.5.1.7 Method 7: Sulfochlorination of Alkenes 219 35.1.5.1.8 Method 8: Selenochlorination of Alkenes 223 35.1.5.1.9 Method 9: Tellurochlorination of Alkenes 227 35.1.5.1.10 Method 10: Aminochlorination of Alkenes 228 35.1.5.1.10.1 Variation 1: Intermolecular Additions 228 35.1.5.1.10.2 Variation 2: Intramolecular Cyclization 238 35.1.5.1.11 Methodii: Phosphochlorination of Alkenes 242 35.1.5.2 Synthesis by Addition across C O Bonds K. Ruck Braun and T. Freysoldt 35.1.5.2 Synthesis by Addition across C 0 Bonds 251 35.1.5.2.1 Method 1: Hydrochlorination of Epoxides Using Hydrogen Chloride — 251 35.1.5.2.2 Method 2: Hydrochlorination of Epoxides Using Elemental Chlorine • • • • 252 35.1.5.2.3 Method 3: Hydrochlorination of Epoxides Using Alkali Metal Chlorides 253 35.1.5.2.4 Method 4: Hydrochlorination of Epoxides Using Chloro(imido)metal Complexes 254 35.1.5.2.5 Method 5: Hydrochlorination of Epoxides Using Silicon Tetrachloride • • • 254 35.1.5.2.5.1 Variation 1: Enantioselective Transformations and Desymmetrization ¦ ¦ • • 255 Table of Contents XXIII 35.1.5.2.6 Method 6: Hydrochlorination of Epoxides UsingTrialkylchlorosilanes ¦•¦ 256 35.1.5.2.7 Method 7: Hydrochlorination of Epoxides Using Chloroorganostannanes 258 35.1.5.2.8 Method 8: Hydrochlorination of Epoxides Using Organoaluminum Chlorides 259 35.1.5.2.9 Method 9: Hydrochlorination of Epoxides Using Lithium Tetrachlorocuprate(ll) 260 35.1.5.2.10 Method 10: Hydrochlorination of Epoxides Using Niobium(V) Chloride ¦•¦ 260 35.1.5.2.11 Method 11: Hydrochlorination of Epoxides Using Titanium(IV) Chloride 261 35.1.5.2.12 Method 12: Hydrochlorination of Epoxides Using Cerium(lll) Chloride — 262 35.1.5.2.13 Method 13: Hydrochlorination of Epoxides Using Tetraalkylammonium Chlorides 262 35.1.5.2.14 Method 14: Hydrochlorination of Epoxides Using Phosphorus Chlorides, Phosphonium Chlorides, Thionyl Chloride, and Related Compounds 263 35.1.5.2.15 Method 15: Hydrochlorination of Epoxides Using Chlorocarbonylated Compounds 265 35.1.5.2.16 Method 16: Hydrochlorination of Tetrahydrofurans and Other Cyclic Ethers 266 35.1.5 3 Synthesis by Addition across C S Bonds K. Ruck Braun and T. Freysoldt 35.1.5.3 Synthesis by Addition across C S Bonds 271 35.1.5.3.1 Method 1: Hydrochlorination of Thiiranes Using Hydrogen Chloride — 271 35.1.5.3.2 Method 2: Hydrochlorination of Thiiranes by Reaction of Thiirane 1 Oxides with Chloro(organo)stannanes 271 35.1.5.3.3 Method 3: Hydrochlorination of Thiiranes Using Chlorocarbonylated Compounds 272 35.1.5.3.4 Method 4: Synthesis by Chlorination of Thiiranes 273 35.1.5.4 Synthesis by Addition across C—N Bonds K. Ruck Braun and T. Freysoldt 35.1.5.4 Synthesis by Addition across C N Bonds 275 35.1.5.4.1 Method 1: Hydrochlorination of Aziridines Using Hydrogen Chloride •¦• 275 35.1.5.4.2 Method 2: Hydrochlorination of Aziridines Using Alkali Metal Chlorides 276 35.1.5.4.3 Method 3: Hydrochlorination of Aziridines Using Other Metal Chlorides 277 35.1.5.4.4 Method 4: Hydrochlorination of Aziridines Using Chlorotrimethylsilane 278 35.1.5.4.5 Method 5: Hydrochlorination of Aziridines Using Activated Dimethylformamide Complexes 278 35.1.5.5 Synthesis by Addition across C C Bonds K. Ruck Braun and T. Freysoldt 35.1.5.5 Synthesis by Addition across C C Bonds 281 35.1.5.5.1 Methodi: Chlorination of 1,1 Diacetylcyclopropane 281 XXIV Table of Contents 3S.2 Product Class 2: One Saturated Carbon—Bromine Bond 35.2.1 Product Subclass 1: Bromoalkanes E. Schaumann 35.2.1 Product Subclass 1: Bromoalkanes 283 35.2.1.1 Synthesis by Substitution of Hydrogen J. Hartung 35.2.1.1 Synthesis by Substitution of Hydrogen 287 35.2.1.1.1 Alkanes and Cycloalkanes 288 35.2.1.1.1.1 Method 1: Bromination with Bromine 288 35.2.1.1.1.2 Method 2: Reaction with tert Butyl Hypobromite 290 35.2.1.1.1.3 Method 3: Brominating Reagents Containing a C—Br Bond 291 35.2.1.1.1.3.1 Variation 1: Carbon Tetrabromide as Bromine Atom Donor 291 35.2.1.1.1.3.2 Variation 2: Bromotrichloromethane as Bromine Atom Donor 291 35.2.1.1.2 Haloalkanes and Halocycloalkanes 292 35.2.1.1.2.1 Method 1: Bromination with Bromine 292 35.2.1.1.3 Aldehydes and Ketones 293 35.2.1.1.3.1 Method 1: Bromination with Bromine 293 35.2.1.1.3.2 Method 2: Reaction with Bromomalonates 294 35.2.1.1.4 Carboxylic Acids and Carboxylic Acid Derivatives 294 35.2.1.1.4.1 Method 1: Bromination with Bromine 294 35.2.1.1.4.2 Method 2: Bromination with N Bromosuccinimide 295 35.2.1.1.5 Isocyanates and Isothiocyanates 296 35.2.1.1.5.1 Method 1: Bromination with N Bromosuccinimide 296 35.2.1.1.6 Alkylboranes and Alkylsilanes 297 35.2.1.1.6.1 Method 1: Bromination with Bromine 297 35.2.1.1.6.2 Method 2: Bromination with N Bromosuccinimide 298 35.2.1.1.7 Carbohydrates 298 35.2.1.1.7.1 Method 1: Bromination with Bromine 298 35.2.1.1.7.2 Method 2: Bromination with N Bromosuccinimide 299 35.2.1 2 Synthesis by Substitution of Metals P. Margaretha 35.2.1.2 Synthesis by Substitution of Metals 301 35.2.1.2.1 Method 1: Bromoalkanes from Organo Group 15 Derivatives 301 35.2.1.2.2 Method 2: Bromoalkanes from Trialkylboranes 301 Table of Contents XXV 35.2.1.3 Substitution of Carbon Functionalities P. Margaretha 35.2.1.3 Substitution of Carbon Functionalities 303 35.2.1.3.1 Method 1: Decarbonylation of Acyl Bromides 303 35.2.1.3.2 Method 2: Bromodecarboxylation of Heavy Metal Salts of Carboxylic Acids 303 35.2.1.3.2.1 Variation 1: Bromodecarboxylation of Silver(l) Carboxylates 303 35.2.1.3.2.2 Variation 2: Bromodecarboxylation of Thallium(l) Carboxylates 304 35.2.1.3.3 Method 3: Bromodecarboxylation of Carboxylic Acids 305 35.2.1.3.3.1 Variation 1: Bromodecarboxylation of Carboxylic Acids in the Presence of Mercury(ll) Oxide 306 35.2.1.3.3.2 Variation 2: Bromodecarboxylation of Carboxylic Acids with (Diacetoxyiodo)benzene and Bromine 306 35.2.1.3.4 Method 4: Bromodecarboxylation of A/ (Acyloxy)pyridine 2(1H) thiones 307 35.2.1.4 Synthesis by Substitution of Other Halogens M. Braun 35.2.1.4 Synthesis by Substitution of Other Halogens 313 35.2.1.4.1 Method 1: Substitution of Fluorine 313 35.2.1.4.1.1 Variation 1: Reaction with Aqueous Hydrogen Bromide 313 35.2.1.4.1.2 Variation 2: Reactions with Lewis Acids 314 35.2.1.4.2 Method 2: Substitution of Chlorine 314 35.2.1.4.2.1 Variation 1: Reaction of Chloroalkanes with Aqueous Hydrogen Bromide 315 35.2.1.4.2.2 Variation 2: Reactions of Chloroalkanes with Gaseous Hydrogen Bromide in the Presence of Iron(lll) Bromide 315 35.2.1.4.2.3 Variation 3: Reactions of Chloroalkanes with Metal Bromides and a Phase Transfer Catalyst 317 35.2.1.4.2.4 Variation 4: Reactions of Chloroalkanes with Bromoalkanes in the Presence of Alkali Metal Bromides 318 35.2.1.4.3 Method 3: Substitution of Iodine 320 35.2.1.4.3.1 Variation 1: Reactions of lodoalkanes with Bromine 320 35.2.1.4.3.2 Variation 2: Reactions of lodoalkanes with Hypervalent lodo Compounds 320 35.2.1.4.3.3 Variation 3: Reactions of lodoalkanes with Bismuth(lll) Bromide 321 35.2.1.5 Synthesis by Substitution of Oxygen Functionalities M. Braun 35.2.1.5 Synthesis by Substitution of Oxygen Functionalities 323 35.2.1.5.1 Method 1: Substitution of Acyloxy Groups in Carboxylic Esters 323 3U.1.5.1.1 Variation 1: Reaction of Carboxylic Esters with Hydrogen Bromide 323 35.2.1.5.1.2 Variation 2: Reaction of Carboxylic Esters with Bromotrimethylsilane — 324 35.2.1.5.1.3 Variation 3: Reaction of Carboxylic Esters with Bromine and Phosphorus 325 3U.1.5.1.4 Variation 4: Reaction of Carboxylic Esters with Triphenylphosphine Bromine 326 XXVI Table of Contents __ 35.2.1.5.2 Method 2: Substitution of Alcoholic Hydroxy Groups 326 35.2.1.5.2.1 Variation 1: Reaction of Alcohols with Aqueous Hydrobromic Acid 326 35.2.1.5.2.2 Variation 2: Reaction of Alcohols with Hydrobromic Acid/Sulfuric Acid ••¦ 328 35.2.1.5.2.3 Variation 3: Reaction of Alcohols with Gaseous Hydrogen Bromide 328 35.2.1.5.2.4 Variation 4: Reaction of Alcohols with Phosphorus Tribromide 329 35.2.1.5.2.5 Variation 5: Reaction of Alcohols with Polymer Bound Phosphorus Tribromide 330 35.2.1.5.2.6 Variation 6: Reaction of Alcohols with Phosphorus Tribromide and Pyridine 331 35.2.1.5.2.7 Variation 7: Reaction of Alcohols with Triphenylphosphine Bromine 331 35.2.1.5.2.8 Variation 8: Reaction of Alcohols with Triphenylphosphine Carbon Tetrabromide and Related Reagents 333 35.2.1.5.2.9 Variation 9: Reaction of Alcohols with Triphenylphosphine N Bromosuccinimide 334 35.2.1.5.2.10 Variation 10: Reaction of Alcohols with Triphenyl Phosphite Bromine 335 35.2.1.5.2.11 Variation 11: Reaction of Alcohols with Bromotrimethylsilane 335 35.2.1.5.2.12 Variation 12: Preparation of Bromoalkanes from Alcohols by a Modified Mitsunobu Procedure 336 35.2.1.5.2.13 Variations 13: Miscellaneous Reactions 337 35.2.1.5.3 Method 3: Substitution of Alcohols with Isomerization 337 35.2.1.5.3.1 Variation 1: Reaction of 1 Cyclopropylalkan 1 ols with Hydrogen Bromide 338 35.2.1.5.3.2 Variation 2: Reaction of 1 Cyclopropylalkan 1 ols with Magnesium Bromide 339 35.2.1.5.3.3 Variation 3: Reaction of 1 Cyclopropylalkan 1 ols with Bromotrimethylsilane Zinc(ll) Bromide 340 35.2.1.5.3.4 Variations 4: Miscellaneous Reactions 341 35.2.1.5.4 Method 4: Cleavage of Alkyl Ethers 341 35.2.1.5.4.1 Variation 1: Reaction of Ethers with Hydrobromic Acid 341 35.2.1.5.4.2 Variation 2: Reaction of Ethers with 9 Bromo 9 borabicyclo[3.3.1]nonane 342 35.2.1.5.5 Method 5: Cleavage of Silyl Ethers 343 35.2.1.5.5.1 Variation 1: Reaction of Silyl Ethers with Triphenylphosphine Bromine 343 35.2.1.5.5.2 Variation 2: Reaction of Silyl Ethers with Triphenylphosphine/ 2,4,4,6 Tetrabromocyclohexa 2,5 dienone 344 35.2.1.5.5.3 Variation 3: Reaction of Silyl Ethers with Triphenylphosphine Carbon Tetrabromide 345 35.2.1.5.5.4 Variation 4: Reaction of Silyl Ethers with Boron Tribromide 346 35.2.1.5.6 Method 6: Substitution of Sulfonyloxy Groups 347 35.2.1.5.6.1 Variation 1: Reaction of Arenesulfonates with Metal Bromides 347 35.2.1.5.6.2 Variation 2: Reaction of Methanesulfonates with Metal Bromides 349 35.2.1.5.6.3 Variations 3: Miscellaneous Reactions 350 Table of Contents XXVII 35.2.1.6 Synthesis by Substitution of Sulfur, Selenium, or Tellurium Functionalities M. Braun 35.2.1.6 Synthesis by Substitution of Sulfur, Selenium, or Tellurium Functionalities 355 35.2.1.6.1 Method 1: Preparation from Sulfides and Cyanogen Bromide or from Selenides and Bromine 355 35.2.1.7 Synthesis by Substitution of Nitrogen Functionalities M. Braun 35.2.1.7 Synthesis by Substitution of Nitrogen Functionalities 357 35.2.1.7.1 Method 1: Synthesis from Amines by the von Braun Reaction 357 35.2.1.7.2 Method 2: Synthesis from Amines via Diazonium Salts 358 35.2.1.8 Synthesis by Addition to re Type C C Bonds K. M. Roy 35.2.1.8 Synthesis by Addition to n Type C C Bonds 361 35.2.1.8.1 Method 1: Hydrobromination of Alkynes or Allenes 362 35.2.1.8.2 Method 2: Hydrobromination of 1,3 Dienes 362 35.2.1.8.2.1 Variation 1: Using Hydrogen Bromide 362 35.2.1.8.2.2 Variation 2: Using Phosphorus Tribromide on Silica Gel 363 35.2.1.8.2.3 Variation 3: Via Hydrozirconation 363 35.2.1.8.3 Method 3: Hydrobromination of Symmetrical Alkenes and Cycloalkenes 364 35.2.1.8.4 Method 4: Hydrobromination of Unsymmetrical Alkenes (MarkovnikovAddition) 364 35.2.1.8.4.1 Variation 1: Using Hydrogen Bromide 364 35.2.1.8.4.2 Variation 2: Using Phase Transfer Conditions 365 35.2.1.8.4.3 Variation 3: Using an Inorganic Support 366 35.2.1.8.5 Method5: Hydrobromination of Unsymmetrical Alkenes (anti Markovnikov Addition) 367 35.2.1.8.5.1 Variation 1: Using Hydrogen Bromide and a Radical Source 367 35.2.1.8.5.2 Variation 2: Using Benzeneselenenyl Bromide and Hydrogen Peroxide • • • 368 35.2.1.8.5.3 Variation 3: Via Hydroboration 369 35J.1.8.5.4 Variation 4: Via Hydroalumination 369 35.2.1.8.5.5 Variation 5: Via Hydrozirconation 370 35.2.1.8.6 Method 6: Asymmetric Hydrobromination of Functionalized Alkenes •¦• 370 35.2.1.8.7 Method 7: Hydrobromination of Methylenecyclopropanes 371 35.2.1.8.7.1 Variation 1: Using Hydrogen Bromide 371 35J.1.8.7.2 Variation 2: Using Titanium(IV) Bromide 371 35.2.1.8.8 Method 8: Hydrobromination of Cyclopropanes 372 35.2.1.8.9 Method 9: Carbobromination 373 35.2.1.8.9.1 Variation 1: Bromocyclization 374 XXVIII Table of Contents 35.2.1.9 Synthesis from Other Bromo Compounds H. Ulrich 35.2.1.9 Synthesis from Other Bromo Compounds 379 35.2.1.9.1 Method 1: Synthesis from Bromoalkynes by Hydrogenation 379 35.2.1.9.2 Method 2: Synthesis from Bromoalkenes 379 35.2.1.9.2.1 Variation 1: By Hydrogenation 379 35.2.1.9.2.2 Variation 2: By Polymerization 380 35.2.1.9.2.3 Variation 3: By Cycloaddition Reactions 380 35.2.1.9.3 Method 3: Synthesis from Bromocarbenes 383 35.2.1.9.4 Method 4: Synthesis from Bromoalkanes 384 35.2.1.9.4.1 Variation 1: By Insertion of Methylene into Carbon—Halogen Bonds 384 35.2.1.9.4.2 Variation 2: By Bromoalkylation 384 35.2.1.9.4.3 Variation 3: By Isomerization Reactions 384 35.2.2 Product Subclass 2: Propargylic Bromides M. Braun 35.2.2 Product Subclass 2: Propargylic Bromides 387 35.2.2.1 Synthesis by Heteroatom Substitution 387 35.2.2.1.1 Method 1: Substitution of Hydroxy Croups 387 35.2.2.1.2 Method 2: Substitution of Sulfonyloxy Croups 389 35.2.3 Product Subclass 3: Benzylic Bromides 35.2.3.1 Synthesis by Substitution of Hydrogen W. D. Pfeiffer 35.2.3.1 Synthesis by Substitution of Hydrogen 391 35.2.3.1.1 Method 1: Reaction with Bromine 391 35.2.3.1.1.1 Variation 1: Reaction with Bromine in the Absence of a Catalyst 391 35.2.3.1.1.2 Variation 2: Reaction with Bromine in the Presence of a Catalyst 393 35.2.3.1.2 Method 2: Reaction with Copper(ll) Bromide 395 35.2.3.1.3 Method 3: Reaction with Sodium Bromide and Hydrogen Peroxide 396 35.2.3.1.4 Method 4: Reaction with Ammonium Cerium(IV) Nitrate/Bromide or Cobalt(lll) Acetate/Bromide 397 35.2.3.1.5 Method 5: Reaction with N Bromosuccinimide 398 35.2.3.1.6 Method 6: Reaction with Ammonium Type Bromides 402 35.2.3.1.6.1 Variation 1: Reaction with a Bromine Complex of Poly(styrene co 4 vinylpyridine) 402 35.2.3.1.6.2 Variation 2: Reaction with Pyridinium Tribromide 403 35.2.3.1.6.3 Variation 3: Reaction with 3 Methylimidazolium Tribromide 404 35.2.3.1.7 Method 7: Reaction with Trichloromethanesulfonyl Bromide 405 35.2.3.1.8 Method 8: Reaction with Bromotrichloromethane 406 Table of Contents XXIX 35.2.3.1.9 Method 9: Reaction with Carbon Tetrabromide 406 35.2.3.1.10 Method 10: Reaction with 4 Bromo 2,4,6 tri tert butylhexa 2,5 dienone 407 35.2.3.2 Synthesis by Substitution of Carbonyl Oxygen W. D. Pfeiffer 35.2.3.2 Synthesis by Substitution of Carbonyl Oxygen 409 35.2.3.2.1 Method 1: Bromomethylation of Arenes 409 35.2.3.2.1.1 Variation 1: Using Paraformaldehyde and Hydrogen Bromide 409 35.2.3.2.1.2 Variation 2: Using Paraformaldehyde, Hydrogen Bromide, and Ultrasound 411 35.2.3.2.1.3 Variation 3: Using 1,3,5 Trioxane and Hydrogen Bromide 412 35.2.3.2.2 Method 2: Alkylation of Arenes with 1,2 Dibromo 1 ethoxyethane 413 35.2.3.2.3 Method 3: Alkylation of Arenes with 1 (Bromomethoxy) 4 chlorobutane or 1,4 Bis(bromomethoxy)butane 413 35.2.3.2.4 Method 4: Bromoalkylation of Arenealdehydes Using Alkylboron Dibromides 414 35.2.3 3 Synthesis by Substitution of o Bonded Heteroatoms M. Braun 35.2.3.3 Synthesis by Substitution of o Bonded Heteroatoms 417 35.2.3.3.1 Method 1: Substitution of Other Halogens 417 35.2.3.3.2 Method 2: Substitution of Oxygen Functionalities 418 35.2.4 Product Subclass 4: Allylic Bromides 35.2.4.1 Synthesis by Substitution of Hydrogen a to a C=C Bond W. D. Pfeiffer 35.2.4.1 Synthesis by Substitution of Hydrogen a to a C=C Bond 423 35.2.4.1.1 Method 1: Allylic Bromination Using Bromine 423 35.2.4.1.2 Method 2: Allylic Bromination Using N Bromosuccinimide 424 35.2.4.1.2.1 Variation 1: Reactions with Aliphatic and Alicyclic Alkenes 424 35.2.4.1.2.2 Variation 2: Reactions with Unsaturated Esters, Nitriles, and Heterocycles 427 35.2.4.1.2.3 Variation 3: Reaction with Allyl(trimethyl)silane 429 35.2.4.1.2.4 Variation 4: Reactions with Isoprenoids 430 35.2.4.1.2.5 Variation 5: Reactions with Steroids 431 35.2.4.1.3 Method 3: Reactions with Halogenated N Bromoacetamides 432 XXX Table of Contents _^_____™^____^^™^ 35.2.4.2 Synthesis by Substitution of o Bonded Heteroatoms M. Braun 35.2.4.2 Synthesis by Substitution of o Bonded Heteroatoms 435 35.2.4.2.1 Method 1: Substitution of Other Halogens 435 35.2.4.2.2 Method 2: Substitution of Oxygen Functionalities 435 35.2.5 Product Subclass 5:1 Bromo n Heteroatom Functionalized Alkanes (n 2) with Both Functions Formed Simultaneously 35.2.5.1 Synthesis by Addition across C=C Bonds T. Troll 35.2.5.1 Synthesis by Addition across C=C Bonds 439 35.2.5.1.1 Method 1: Bromination of Aromatic Compounds 440 35.2.5.1.2 Method 2: Bromination of 1,3 Dienes 441 35J.5.1.3 Method 3: Bromination of Alkenes 445 35.2.5.1.3.1 Variation 1: Bromination with Bromine Amine Complexes 464 35.2.5.1.3.2 Variation 2: Generation of Electrophilic Bromine by In Situ Oxidation of Bromide 465 35.2.5.1.4 Method 4: Hydroxy and Alkoxybromination of Alkenes 471 35.2.5.1.5 Method 5: Sulfobromination of Alkenes 484 35.2.5.1.6 Method 6: Aminobromination of Alkenes 485 3S.2.5.U Method 7: Azidobromination of Alkenes 492 35.2.5.1.8 Method 8: Phosphobromination of Alkenes 493 35.2.5.2 Synthesis by Addition across C 0 Bonds K. Riick Braun and T. Freysoldt 35.2.5.2 Synthesis by Addition across C O Bonds 503 35.2.5.2.1 Method 1: Hydrobromination of Epoxides Using Hydrogen Bromide — 504 35.2.5.2.2 Method 2: Hydrobromination of Epoxides Using Elemental Bromine — 505 35.2.5.2.3 Method 3: Hydrobromination of Epoxides Using Alkali Metal Bromides 506 35.2.5.2.3.1 Variation 1: Catalyzed by Lewis Acids 508 35.2.5.2.4 Method 4: Hydrobromination of Epoxides Using Magnesium Bromide 508 35.2.5.2.5 Method 5: Hydrobromination of Epoxides Using Tin(ll) Bromide 510 35.2.5.2.6 Method 6: Hydrobromination of Epoxides Using Bromo(imido)metal Complexes 510 35.2.5.2.7 Method 7: Enantioselective Hydrobromination of Epoxides Using Azidotrialkylsilanes and Ally! Bromide 511 35J.5.2.8 Method 8: Hydrobromination of Epoxides Using Boron Bromides 512 35.2.5.2.8.1 Variation 1: Enantioselective Transformations 513 35J.5.2.9 Method 9: Hydrobromination of Epoxides Using Lithium Tetrabromocuprate(ll) 513 Table of Contents XXXI 35.2.5.2.10 Method 10: Hydrobromination of Epoxides Using Lithium Tetrabromonickelate(ll) 514 35.2.5.2.11 Method 11: Hydrobromination of Epoxides Using Ammonium Bromides 514 35.2.5.2.12 Method 12: Hydrobromination of Epoxides Using Phosphorus Tribromide or Phosphonium Bromides 515 35.2.5.2.13 Method 13: Hydrobromination of Tetrahydrofurans and Oxetanes 518 35.2.5.3 Synthesis by Addition across C S Bonds K. Riick Braun and T. Freysoldt 35.2.5.3 Synthesis by Addition across C—S Bonds 523 35.2.5.3.1 Method 1: Hydrobromination of Thiiranes Using Methanesulfenyl Bromide 523 35.2.5.3.2 Method 2: Hydrobromination of Thiiranes Using Bromo(organo)stannanes 523 35.2.5.3.3 Method 3: Synthesis by Bromination of Thiiranes 524 35.2.5.4 Synthesis by Addition across C N Bonds K. Ruck Braun and T. Freysoldt 35.2.5.4 Synthesis by Addition across C N Bonds 527 35.2.5.4.1 Method 1: Hydrobromination of Aziridines Using Hydrogen Bromide ¦¦• 527 35.2.5.4.2 Method 2: Hydrobromination of Aziridines Using Alkali Metal Bromides 528 35.2.5.4.3 Method 3: Hydrobromination of Aziridines Using Other Metal Bromides 529 35.2.5.4.4 Method 4: Hydrobromination of Aziridines Using Tetraalkylammonium Bromides 531 35.2.5.4.5 Method 5: Hydrobromination of Aziridines with Bromotrimethylsilane 532 35.2.5.4.6 Method 6: Hydrobromination of Aziridines Using Activated Dimethylformamide Complexes 532 35.2.5.4.7 Method 7: Hydrobromination of Aziridines Using Benzyl Bromides 533 35.2.5 5 Synthesis by Addition across C C Bonds K. Riick Braun and T. Freysoldt 35.2.5.5 Synthesis by Addition across C C Bonds 535 35.2.5.5.1 Method 1: Bromination of Pentafluoro(vinyl)cyclopropanes 535 353 Product Class 3: One Saturated Carbon—Iodine Bond 35 J.i Product Subclass 1: lodoalkanes E. Schaumann 35J.1 Product Subclass 1: lodoalkanes 537 XXXII Table of Contents 353.1.1 Synthesis by Substitution of Hydrogen J. Hartung 353.1.1 Synthesis by Substitution of Hydrogen 541 353.1.1.1 Method 1: Alkane Functionalization in the Presence of Polyiodomethanes and Sodium Hydroxide 542 353.1.1.2 Method 2: Alkane Functionalization in the Presence of Nonafluoro 1 iodobutane 543 353.1.1.3 Method 3: Alkane Functionalization in the Presence of tert Butyl Hypoiodite 544 353.1.1.4 Method 4: Alkane Functionalization in the Presence of Iodine and (Diacetoxyiodo)benzene in Alcohols 545 353.1.1.5 Method 5: Alkane Functionalization with Iodine in the Presence of Aluminum Triiodide and Tetrahalomethanes 546 353.1.2 Synthesis by Substitution of Metals S. Hartinger and M. Hartinger 353.1.2 Synthesis by Substitution of Metals 549 353.1.2.1 Method 1: Synthesis from Compounds of the Alkali or Alkaline Earth Metals 549 353.1.2.2 Method 2: Synthesis from Organomercury Compounds 553 353.1.2.3 Method 3: Synthesis from Organozinc Reagents 555 353.1.2.4 Method 4: Synthesis from Organostannane Compounds 557 353.1.2.5 Method 5: Synthesis from Organosilicon Compounds 558 353.1.2.6 Method 6: Synthesis from Organoboranes or Organoaluminum Compounds 560 353.1.3 Synthesis by Substitution of Carbon Functionalities S. Hartinger and M. Hartinger 353.1.3 Synthesis by Substitution of Carbon Functionalities 565 353.1.3.1 Method 1: Synthesis from Aliphatic Acids by Decarboxylation with Hypervalent Iodine Compounds 565 353.1.3.2 Method 2: Synthesis from Aliphatic Acids by Decarboxylation with tert Butyl Hypoiodite 567 353.1.3.3 Method 3: Synthesis from Aliphatic Acids by Decarboxylation with Organic Peroxides 568 353.1.3.4 Method 4: Synthesis from N (Acyloxy)pyridine 2(1H) thiones by Degradation 569 353.1.3.5 Method 5: Synthesis from Salts of Aliphatic Acids by Degradation (Hunsdiecker Reaction) 571 353.1.3.5.1 Variation 1: Synthesis from Mercury(ll) Carboxylates of Aliphatic Acids •¦ 572 353.1.3.5.2 Variation 2: Synthesis from Lead(IV) Salts of Aliphatic Acids 573 353.1.3.6 Method 6: Synthesis from Aliphatic Esters or Acid Chlorides by O Silylation 574 ^ Table of Contents ..„„__„..., „.„„„„., XXXIII 35.3.1.3.7 Method 7: Synthesis from Aliphatic Peroxyacids and Hydroperoxides by Degradation 575 35.3.1.4 Synthesis by Substitution of Other Halogens S. Hartinger and M. Hartinger 353.1.4 Synthesis by Substitution of Other Halogens 579 353.1.4.1 Method 1: Synthesis from Chloro or Bromoalkanes with Alkali Metal Iodides 579 353.1.4.2 Method 2: Synthesis from Chloro and Bromoalkanes under Phase Transfer Catalysis 581 353.1.4.3 Method 3: Synthesis from Haloalkanes by Iodide Catalyzed Exchange Reactions 582 353.1.4.4 Method 4: Synthesis from Haloalkanes with Hydriodic Acid 583 353.1.4.5 Method 5: Synthesis from Haloalkanes with lodosilanes 584 353.1.5 Synthesis by Substitution of Oxygen Functionalities S. Hartinger 353.1.5 Synthesis by Substitution of Oxygen Functionalities 589 353.1.5.1 Method 1: Synthesis from Aliphatic Carbonyl Compounds or Acetals ¦•¦ 589 353.1.5.1.1 Variation 1: Reductive lodination with an Amine Borane Complex 590 353.1.5.1.2 Variation 2: Reductive lodination with Diiodosilane 591 353.1.5.1.3 Variation 3: Direct lodination of the Tetrahydropyran 2 yloxy Group 592 353.1.5.2 Method 2: Synthesis from Aliphatic Carboxylic Acid Esters 593 353.1.5.2.1 Variation 1: Cleavage with Hydriodic Acid 594 353.1.5.2.2 Variation 2: Metal Catalyzed lodinolysis 595 353.1.5.2.3 Variation 3: Cleavage of an Acyloxy or a Chloroalkyl Carbonate Group with Metal Iodides 596 353.1.5.2.4 Variation 4: Cleavage of an Acyloxy, Formyloxy, or Carbamate Group with lodotrimethylsilane 598 353.1.5.2.5 Variation 5: Reaction with lodomethane 599 353.1.5.2.6 Variation 6: Decarboxylation of a Chloroformate Group 600 353.1.5.3 Method 3: Synthesis from Cyclic Alcohols or Ketones, Lactols, or Hydroxymethyl Substituted Cycloalkanes by Isomerization and Fragmentation 601 353.1.5.3.1 Variation 1: Alkoxyl Radical Mediated Reactions 601 353.1.5.3.2 Variation 2: Ring Expanded Iodides by Wagner Meerwein Rearrangement 609 353.1.5.3.3 Variation 3: Ring Opening and Fragmentation Reactions of Cyclopropyl Alcohols 610 353.1.5.3.4 Variation 4: Ring Opening Reactions of Cyclobutanones 612 353.1.5.4 Method 4: Synthesis from Ethers 613 353.1.5.4.1 Variation 1: Cleavage with Hydriodic Acid 613 353.1.5.4.2 Variation 2: Cleavage with Alkali Metal Iodides and Acids 615 353.1.5.4.3 Variation 3: lodinolysis with Borohydride Reagents 616 353.1.5.4.4 Variation 4: Cleavage with lodosilane Reagents 617 XXXIV Table of Contents _________™_™___ 353.1.5.4.5 Variation 5: Cleavage of a Trimethylsiloxy Group 619 353.1.5.4.6 Variation 6: Cleavage with Carboxylic Acid Iodides 620 35.3.1.5.4.7 Variation?: Activation with Metal Containing Lewis Acids 622 353.1.5.5 Method 5: Synthesis from Esters of Sulfur, Nitrogen, or Phosphorus Oxyacids 623 353.1.5.5.1 Variation 1: Cleavage of a Sulfonyloxy Group with Metal Iodides 623 353.1.5.5.2 Variation 2: Phase Transfer Catalyzed Cleavage of a Sulfonyloxy Group ¦• 628 353.1.5.5.3 Variation 3: Nucleophilic Substitution in Ionic Liquids 631 35.3.1.5.5.4 Variation 4: Cleavage of Ammonioalkanesulfonate Esters 632 353.1.5.5.5 Variation 5: Cleavage of Dialkyl Sulfates 633 353.1.5.5.6 Variation 6: Cleavage of Esters or Amides of Mononuclear Oxyacids of Phosphorus 633 353.1.5.6 Method 6: Synthesis from Alcohols 635 353.1.5.6.1 Variation 1: Direct lodinolysis 635 353.1.5.6.2 Variation 2: lodination with Hydriodic Acid 636 353.1.5.6.3 Variation 3: lodination with Metal Iodides and Acid as a Source of Hydriodic Acid 638 353.1.5.6.4 Variation 4: lodination with Metal Iodides and 70% Hydrogen Fluoride/Pyridine 639 353.1.5.6.5 Variation 5: lodination with Metal Iodides 640 353.1.5.6.6 Variation 6: Iodine Transfer from Organic or Organometallic Iodides 642 353.1.5.6.7 Variation?: Activation with Diazolides 643 353.1.5.6.8 Variation 8: Activation with O Alkylisoureas 644 353.1.5.6.9 Variation 9: Activation with Alkoxyformamidinium Salts 646 353.1.5.6.10 Variation 10: Activation with Onium Salts of 2 Fluoroazaarenes 647 353.1.5.6.H Variation 11: lodination with Phosphorus and Iodine or with Phosphorus Triiodide 648 353.1.5.6.12 Variation 12: Activation with Phosphite Esters or Phosphorus Amides 649 353.1.5.6.13 Variation 13: Activation with Phosphine Reagents 652 353.1.5.6.14 Variation 14: lodination with lodosilane Reagents 656 353.1.5.6.15 Variation 15: lodinolysis with Borane or Boronate Reagents 657 353.1.5.6.16 Variation 16: lodination in Ionic Liquids 659 353.1.6 Synthesis by Substitution of Sulfur, Selenium, or Tellurium Functionalities S. Hartinger and M. Hartinger 353.1.6 Synthesis by Substitution of Sulfur, Selenium, or Tellurium Functionalities 673 353.1.6.1 Method 1: Reaction of Aliphatic Sulfur or Selenium Compounds with Phosphine Reagents and Iodine 673 353.1.6.2 Method 2: Synthesis from Alkyl Sulfides via Formation of Sulfonium Salts 675 Table of Contents XXXV 353.1.7 Synthesis by Substitution of Nitrogen Functionalities S. Hartinger and M. Hartinger 35.3.1.7 Synthesis by Substitution of Nitrogen Functionalities 679 353.1.7.1 Method 1: Synthesis from Alkylamines via Formation of Trialkylammonium Salts 679 353.1.7.2 Method 2: Synthesis from Alkylamines via Pyrolysis of 1 Alkylpyridinium Salts 680 353.1.7.3 Method 3: Synthesis from Alkylamines via Formation of N Alkyl N.N disulfonylamines 681 353.1.7.4 Method 4: Synthesis from Hydrazines by lodinolysis 682 353.1.7.5 Method 5: Synthesis from Nitroalkanes by Substitution 683 353.1.8 Synthesis by Addition to Ji Type C—C Bonds K. M. Roy 353.1.8 Synthesis by Addition to Jt Type C C Bonds 685 353.1.8.1 Method!: Hydroiodination of 1,3 Dienes 685 353.1.8.1.1 Variation 1: Synthesis of 1 lodo 3 methylbut 2 ene with Phosphorus Triiodide/Silica Gel 685 353.1.8.2 Method 2: Hydroiodination of Alkenes and Cycloalkenes (Markovnikov Addition) 686 353.1.8.2.1 Variation 1: Synthesis Using Hydrogen Iodide 686 353.1.8.2.2 Variation 2: Surface Mediated Synthesis 687 353.1.8.3 Method 3: Hydroiodination of Alkenes and Cycloalkenes (anti Markovnikov Addition) 688 353.1.8.3.1 Variation 1: Synthesis via Hydroboration 688 353.1.8.3.2 Variation 2: Synthesis via Hydroalumination 689 353.1.8.3.3 Variation 3: Synthesis via Hydrozirconation 690 353.1.8.4 Method 4: Hydroiodination of Methylenecyclopropanes 691 353.1.8.5 Method 5: Hydroiodination of Cyclopropanes 691 353.1.8.6 Method 6: Carboiodination 692 353.1.8.6.1 Variation 1: lodocyclization 693 353.1.9 Synthesis from Other lodo Compounds H. Ulrich 353.1.9 Synthesis from Other lodo Compounds 697 353.1.9.1 Method 1: Synthesis from lodoalkynes 697 353.1.9.1.1 Variation 1: By Cycloaddition Reactions 697 353.1.9.2 Method 2: Synthesis from lodoalkenes 697 353.1.9.2.1 Variation 1: By Hydrogenation 697 353.1.9.2.2 Variation 2: By Polymerization 697 353.1.9.2.3 Variation 3: By Cycloaddition Reactions 698 353.1.9.3 Method 3: Synthesis from lodocarbenes 698 353.1.9.4 Method 4: Synthesis from lodoalkanes 699 XXXVI Table of Contents .__. 353.1.9.4.1 Variation 1: By lodoalkylation Reactions 699 353.1.9.4.2 Variation 2: By Isomerization Reactions 699 35.3.2 Product Subclass 2: Propargylic Iodides S. Hartinger 353.2 Product Subclass 2: Propargylic Iodides 701 353.2.1 Synthesis of Product Subclass 2 701 353.2.1.1 Method 1: Chemoselective Substitution of Heteroatoms 701 353.2.1.2 Method 2: Modification of the Carbon Skeleton 702 353.3 Product Subclass 3: Benzylic Iodides 353.3.1 Synthesis by Substitution of Carbonyl Oxygen W. D. Pfeiffer 353.3.1 Synthesis by Substitution of Carbonyl Oxygen 705 353.3.1.1 Method 1: Photochemical lodination at the Benzylic Position 705 353.3.1.2 Method 2: lodomethylation of an Arene Using Chloromethyl Methyl Ether and Hydrogen Iodide 705 353.3.2 Substitution of o Bonded Heteroatoms S. Hartinger and M. Hartinger 353.3.2 Substitution of o Bonded Heteroatoms 707 353.3.2.1 Method 1: Synthesis by Substitution of o Bonded Heteroatoms 707 353.4 Product Subclass 4: Alh/lic Iodides S. Hartinger 353.4 Product Subclass 4: Allylk Iodides 711 353.4.1 Synthesis of Product Subclass 4 711 353.4.1.1 Method 1: Synthesis by Regioselective Substitution of Heteroatoms — 711 353.4.1.2 Method 2: Synthesis by Regioselective Addition to the Carbon Skeleton 712 Table of Contents XXXVII 35.3.5 Product Subclass 5:1 lodo n Heteroatom Functionalized Alkanes (n 2) with Both Functions Formed Simultaneously 353.5.1 Synthesis by Addition across C=C Bonds T. Troll 353.5.1 Synthesis by Addition across C=C Bonds 717 353.5.1.1 Method 1: lodination of Alkenes 717 353.5.1.2 Method 2: Hydroxy or Alkoxyiodination of Alkenes 718 353.5.1.2.1 Variation 1: Oxidation of Iodide by Hydrogen Peroxide 718 353.5.1.2.2 Variation 2: lodocyclization of Enols 719 353.5.1.2.3 Variation 3: lodination To Form lodo Acetates 720 353.5.1.2.4 Variation 4: lodohydrins Using Hypoiodous Acid 720 353.5.1.2.5 Variation 5: lodohydrins Using Hypervalent Iodine Compounds 722 353.5.1.2.6 Variation 6: lodohydrins Using /V lodosuccinimide 725 353.5.1.3 Method 3: lodosulfonation of Alkenes 729 353.5.1.4 Method 4: Azido and Aminoiodination of Alkenes 731 353.5.2 Synthesis by Addition across C O Bonds K. Riick Braun and T. Freysoldt 353.5.2 Synthesis by Addition across C O Bonds 741 353.5.2.1 Method 1: Hydroiodination of Epoxides Using Hydrogen Iodide 741 353.5.2.2 Method 2: Hydroiodination of Epoxides Using Elemental Iodine 742 353.5.2.3 Method 3: Hydroiodination of Epoxides Using Alkali Metal Iodides 743 353.5.2.3.1 Variation 1: Catalyzed by Lewis Acids 745 353.5.2.4 Method 4: Hydroiodination of Epoxides Using Magnesium Iodide 746 353.5.2.5 Method 5: Enantioselective Hydroiodination of Epoxides Using Trialkylazidosilanes and Allyl Iodide 747 353.5.2.6 Method 6: Hydroiodination of Epoxides Using Samarium(ll) Iodide 748 353.5.2.7 Method 7: Hydroiodination of Epoxides Using Phosphorus Iodides and Phosphonium Iodides 749 353.5.2.8 Method 8: lodination of Epoxides and Other Cyclic Ethers 750 353.5.3 Synthesis by Addition across C—S Bonds K. RCick Braun and T. Freysoldt 353.5.3 Synthesis by Addition across C S Bonds 753 353.5.3.1 Method 1: Synthesis by lodination of Thiiranes 753 XXXVIII Table of Contents 353.5.4 Synthesis by Addition across C—N Bonds K. Ruck Braun and T. Freysoldt 35.3.5.4 Synthesis by Addition across C—N Bonds 757 353.5.4.1 Method 1: Hydroiodination of Aziridines Using Hydrogen Iodide 757 353.5.4.2 Method 2: Hydroiodination of Aziridines Using Alkali Metal Iodides 757 353.5.4.3 Method 3: Hydroiodination of Aziridines Using Other Metal Iodides — 759 353.5.4.4 Method 4: Hydroiodination of Aziridines Using Indium(lll) or Zinc(ll) Iodide 759 353.5.4.5 Method 5: Hydroiodination of Aziridines Using Samarium(ll) Iodide — 760 353.5.4.6 Method 6: Hydroiodination of Aziridines Using lodotrimethylsilane 761 353.5.5 Synthesis by Addition across C—C Bonds K. Ruck Braun and T. Freysoldt 353.5.5 Synthesis by Addition across C—C Bonds 763 353.5.5.1 Method 1: Ring Opening of Cyclopropanes Using Mercury(ll) Salts and Iodine 763 353.5.5.2 Method 2: Ring Opening of Vinylcyclopropanes 764 353.5.5.3 Method 3: lodination of 1,1 Diacetylcyclopropane 765 Keyword Index 767 Author Index 805 Abbreviations 845
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spellingShingle	Braun, M. Science of synthesis Houben-Weyl methods of molecular transformations
title	Science of synthesis Houben-Weyl methods of molecular transformations
title_auth	Science of synthesis Houben-Weyl methods of molecular transformations
title_exact_search	Science of synthesis Houben-Weyl methods of molecular transformations
title_full	Science of synthesis Houben-Weyl methods of molecular transformations 35 = Category 5, Compounds with one saturated carbon-heteroatom bond Chlorine, bromine, and iodine ed. board: D. Bellus ...
title_fullStr	Science of synthesis Houben-Weyl methods of molecular transformations 35 = Category 5, Compounds with one saturated carbon-heteroatom bond Chlorine, bromine, and iodine ed. board: D. Bellus ...
title_full_unstemmed	Science of synthesis Houben-Weyl methods of molecular transformations 35 = Category 5, Compounds with one saturated carbon-heteroatom bond Chlorine, bromine, and iodine ed. board: D. Bellus ...
title_short	Science of synthesis
title_sort	science of synthesis houben weyl methods of molecular transformations chlorine bromine and iodine
title_sub	Houben-Weyl methods of molecular transformations
url	http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=015420318&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA
volume_link	(DE-604)BV013247070
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