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Chlorine, Bromine, and Iodine
Using Phosphorus Pentachloride
other
Author(s):
P. Margaretha
Publication date
(Online):
2007
Publisher:
Georg Thieme Verlag KG
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Author and book information
Book Chapter
Publication date (Print):
2007
Publication date (Online):
2007
Page
: 1
DOI:
10.1055/sos-SD-035-00076
SO-VID:
b08b063e-daac-4470-848c-7fe45eddfee6
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Book chapters
pp. 1
Synthesis of 1-Iodo-3-methylbut-2-ene with Phosphorus Triiodide/Silica Gel
pp. 1
Enantioselective Hydrobromination of Epoxides Using Azidotrialkylsilanes and Allyl Bromide
pp. 1
Reaction of Aliphatic Sulfur or Selenium Compounds with Phosphine Reagents and Iodine
pp. 1
Carbon Tetrabromide as Bromine-Atom Donor
pp. 1
Synthesis from Chloroalkynes by Hydrogenation
pp. 1
Bromoalkanes from Trialkylboranes
pp. 1
Reactions of Iodoalkanes with Bismuth(III) Bromide
pp. 1
Substitution of Bromine
pp. 1
In the Presence of Bismuth(III) Chloride
pp. 1
Synthesis Using an Inorganic Support
pp. 1
Hydroiodination of Cyclopropanes
pp. 1
Reaction with Bromine
pp. 1
Chlorination with Carbon Tetrachloride in the Presence of Transition-Metal Carbonyl Complexes
pp. 1
Reaction of Alcohols with Triphenyl Phosphite–Bromine
pp. 1
Enantioselective Transformations and Desymmetrization
pp. 1
Reductive Iodination with an Amine–Borane Complex
pp. 1
Reaction with 1,3,5-Trichloro-1,3,5-triazine-2,4,6(1,3,5)-trione (Trichloroisocyanuric Acid)
pp. 1
Benzylic Chlorides from Benzylic Bromides Using Tin(IV) Chloride
pp. 1
Hydrochlorination of Epoxides Using Lithium Tetrachlorocuprate(II)
pp. 1
Using 1,3,5-Trioxane and Hydrogen Bromide
pp. 1
Reductive Iodination with Diiodosilane
pp. 1
Bromodecarboxylation of Heavy-Metal Salts of Carboxylic Acids
pp. 1
Activation with Alkoxyformamidinium Salts
pp. 1
Sulfochlorination of Alkenes
pp. 1
Reaction of Carboxylic Esters with Bromine and Phosphorus
pp. 1
Ketones
pp. 1
Tellurochlorination of Alkenes
pp. 1
Alkane Functionalization in the Presence of Nonafluoro-1-iodobutane
pp. 1
Synthesis from Salts of Aliphatic Acids by Degradation (Hunsdiecker Reaction)
pp. 1
Surface-Mediated Synthesis
pp. 1
Synthesis via Hydroalumination
pp. 1
Hydrochlorination of Tetrahydrofurans and Other Cyclic Ethers
pp. 1
Phosphobromination of Alkenes
pp. 1
Hydrobromination of Epoxides Using Elemental Bromine
pp. 1
Reaction of Alcohols with Gaseous Hydrogen Bromide
pp. 1
Reaction with Chlorine and a Catalyst
pp. 1
Synthesis from Amines by the von Braun Reaction
pp. 1
Synthesis from Primary Aliphatic Amines
pp. 1
Reaction with Ammonium-Type Bromides
pp. 1
Alkylboranes and Alkylsilanes
pp. 1
Enantioselective Transformations
pp. 1
Synthesis from Aliphatic Acids by Decarboxylation with -Butyl Hypoiodite
pp. 1
Hydrobromination of Epoxides Using Ammonium Bromides
pp. 1
Hydroxy- and Alkoxybromination of Alkenes
pp. 1
Synthesis by Chlorination of Thiiranes
pp. 1
By Insertion of Methylene into Carbon—Halogen Bonds
pp. 1
Sulfobromination of Alkenes
pp. 1
In the Absence of a Solvent
pp. 1
Substitution of Fluorine
pp. 1
Synthesis by Heteroatom Substitution
pp. 1
Chloromethylation with 1,3,5-Trioxane
pp. 1
Iodocyclization
pp. 1
Hydrobromination of 1,3-Dienes
pp. 1
Hydrobromination of Aziridines Using Activated Dimethylformamide Complexes
pp. 1
Reaction of Silyl Ethers with Triphenylphosphine–Bromine
pp. 1
Synthesis Using Thionyl Chloride
pp. 1
Phosphochlorination of Alkenes
pp. 1
Reaction with Bromotrichloromethane
pp. 1
Bromoalkylation of Arenealdehydes Using Alkylboron Dibromides
pp. 1
In the Presence of an Equimolar Amount of 1-Benzotriazole
pp. 1
Synthesis Using Hydrogen Iodide
pp. 1
Alkylation of Arenes with 1-(Bromomethoxy)-4-chlorobutane or 1,4-Bis(bromomethoxy)butane
pp. 1
Hydrobromination of Thiiranes Using Methanesulfenyl Bromide
pp. 1
Reaction of Silyl Ethers with Triphenylphosphine–Carbon Tetrabromide
pp. 1
Reactions of Chloroalkanes with Bromoalkanes in the Presence of Alkali Metal Bromides
pp. 1
Reactions with Trichloromethanesulfenyl Chloride
pp. 1
Reaction with Phosphorus Pentachloride
pp. 1
Reaction of Silyl Ethers with Boron Tribromide
pp. 1
Bromodecarboxylation of -(Acyloxy)pyridine-2(1)-thiones
pp. 1
Reaction with Ammonium Cerium(IV) Nitrate–Lithium Chloride or Cobalt(III) Acetate–Lithium Chloride
pp. 1
Synthesis from Tertiary Aliphatic Amines
pp. 1
Bromination with Bromine–Amine Complexes
pp. 1
[2+2]-Cycloaddition Reactions
pp. 1
Iodinolysis with Borohydride Reagents
pp. 1
Alkoxyl-Radical-Mediated Reactions
pp. 1
Hydroiodination of Epoxides Using Samarium(II) Iodide
pp. 1
Iodinolysis with Borane or Boronate Reagents
pp. 1
Reaction of Carboxylic Esters with Bromotrimethylsilane
pp. 1
Substitution of Other Halogens
pp. 1
Chloromethylation with 1-Chloro-4-(chloromethoxy)butane or 1,4-Bis(chloromethoxy)butane
pp. 1
Hydrochlorination of Epoxides Using Trialkylchlorosilanes
pp. 1
Synthesis from Chloroalkanes
pp. 1
Hydroiodination of Alkenes and Cycloalkenes (Markovnikov Addition)
pp. 1
Hydrochlorination of Epoxides Using Silicon Tetrachloride
pp. 1
Alkane Functionalization in the Presence of Polyiodomethanes and Sodium Hydroxide
pp. 1
Cleavage with Zinc and Acetyl Chloride
pp. 1
Using Sodium or Potassium Chloride
pp. 1
Oxidation of Iodide by Hydrogen Peroxide
pp. 1
Preparation from Sulfides and Cyanogen Bromide or from Selenides and Bromine
pp. 1
Cleavage of a Sulfonyloxy Group with Metal Iodides
pp. 1
Bromination with Bromine
pp. 1
Hydrochlorination of Thiiranes by Reaction of Thiirane 1-Oxides with Chloro(organo)stannanes
pp. 1
Using Sulfuryl Chloride
pp. 1
Reaction with Chlorine under Irradiation
pp. 1
Synthesis from Iodoalkenes
pp. 1
Allylic Chlorides from Allyloxybenzenes
pp. 1
Hydrochlorination of Thiiranes Using Hydrogen Chloride
pp. 1
Reaction with Chlorine Monoxide
pp. 1
Reaction with -Butyl Hypochlorite
pp. 1
Hydrochlorination of Aziridines Using Chlorotrimethylsilane
pp. 1
Carbohydrates
pp. 1
Via Hydroalumination
pp. 1
Asymmetric Hydrobromination of Functionalized Alkenes
pp. 1
Synthesis from Bromocarbenes
pp. 1
Chloroalkylation with Aldehydes
pp. 1
Cleavage of an Acyloxy or α-Chloroalkyl Carbonate Group with Metal Iodides
pp. 1
Reaction of Carboxylic Esters with Hydrogen Bromide
pp. 1
Reaction of Alcohols with Triphenylphosphine–Carbon Tetrabromide and Related Reagents
pp. 1
Aminobromination of Alkenes
pp. 1
In the Presence of an Equimolar Amount of Pyridine
pp. 1
Alkane Functionalization in the Presence of Iodine and (Diacetoxyiodo)benzene in Alcohols
pp. 1
Chloromethylation with Paraformaldehyde and Hydrogen Chloride
pp. 1
Synthesis from Iodocarbenes
pp. 1
Chloromethylation with Methoxyacetyl Chloride and Aluminum Trichloride
pp. 1
Reactions with Chloroamines
pp. 1
Hydroxy- or Alkoxyiodination of Alkenes
pp. 1
Chloroalkylation with Acetaldehyde
pp. 1
Substitution of Sulfonyloxy Groups
pp. 1
Reaction with Ammonium Cerium(IV) Nitrate/Bromide or Cobalt(III) Acetate/Bromide
pp. 1
In the Presence of Selenium Dioxide
pp. 1
Reactions with Molecular Chlorine
pp. 1
Hydrobromination of Thiiranes Using Bromo(organo)stannanes
pp. 1
Reaction with Hypochlorous Acid
pp. 1
Bromination of 1,3-Dienes
pp. 1
Hydrobromination of Epoxides Using Magnesium Bromide
pp. 1
Ring Opening and Fragmentation Reactions of Cyclopropyl Alcohols
pp. 1
Cleavage with Iodosilane Reagents
pp. 1
Substitution of Alcoholic Hydroxy Groups
pp. 1
Reaction of Arenesulfonates with Metal Bromides
pp. 1
Synthesis from Organomercury Compounds
pp. 1
Hydrobromination of Epoxides Using Boron Bromides
pp. 1
Carboxylic Acids and Carboxylic Acid Derivatives
pp. 1
Reaction of Ethers with Hydrobromic Acid
pp. 1
Synthesis from Chloro- and Bromoalkanes under Phase-Transfer Catalysis
pp. 1
Replacement of an Alcoholic Hydroxy Group with Chlorides of Phosphoric Acid and Related Compounds
pp. 1
Synthesis from Propargylic Alcohols and Thionyl Chloride
pp. 1
Reaction with a Bromine Complex of Poly(styrene--4-vinylpyridine)
pp. 1
Synthesis from Hydrazines by Iodinolysis
pp. 1
Activation with -Alkylisoureas
pp. 1
Hydrochlorination of 1,3-Dienes
pp. 1
Reaction of Alcohols with Phosphorus Tribromide
pp. 1
Hydrobromination of Symmetrical Alkenes and Cycloalkenes
pp. 1
Bromodecarboxylation of Silver(I) Carboxylates
pp. 1
Synthesis Using 4-Toluenesulfonyl Chloride
pp. 1
Synthesis with Metal Chlorides
pp. 1
Synthesis from Cyclic Alcohols or Ketones, Lactols, or Hydroxymethyl-Substituted Cycloalkanes by Isomerization and Fragmentation
pp. 1
Iodination To Form Iodo Acetates
pp. 1
Synthesis from Nitroalkanes by Substitution
pp. 1
Ring Opening of Vinylcyclopropanes
pp. 1
Substitution of Oxygen Functionalities
pp. 1
Synthesis with Hydrogen Chloride
pp. 1
Reactions with Sulfuryl Chloride
pp. 1
Hydrochlorination of Thiiranes Using Chlorocarbonylated Compounds
pp. 1
Replacement of an Alcoholic Hydroxy Group with Acetyl Chloride
pp. 1
Hydroiodination of Aziridines Using Alkali Metal Iodides
pp. 1
Metal-Catalyzed Iodinolysis
pp. 1
Benzylic Chlorides from Benzylic Ethers
pp. 1
Reaction of Alcohols with Phosphorus Tribromide and Pyridine
pp. 1
Chlorination of 1,1-Diacetylcyclopropane
pp. 1
Using Pyridinium Hydrochloride
pp. 1
Allylic Chlorides from Allylic Phosphates
pp. 1
Reaction of Ethers with 9-Bromo-9-borabicyclo[3.3.1]nonane
pp. 1
Iodination with Metal Iodides and 70% Hydrogen Fluoride/Pyridine
pp. 1
-Butyl Hypochlorite as Chlorine-Atom Donor
pp. 1
Synthesis of Product Subclass 4
pp. 1
Hydrobromination of Unsymmetrical Alkenes (Markovnikov Addition)
pp. 1
Hydroiodination of Epoxides Using Alkali Metal Iodides
pp. 1
Hydrobromination of Methylenecyclopropanes
pp. 1
Iodination of 1,1-Diacetylcyclopropane
pp. 1
With Thionyl Chloride
pp. 1
Phase-Transfer-Catalyzed Cleavage of a Sulfonyloxy Group
pp. 1
Reaction with -Butyl Hypobromite
pp. 1
Hydrochlorination of Polyenes
pp. 1
Iodination of Epoxides and Other Cyclic Ethers
pp. 1
Using Benzeneselenenyl Bromide and Hydrogen Peroxide
pp. 1
Synthesis from Alcohols
pp. 1
Hydroiodination of Alkenes and Cycloalkenes (anti-Markovnikov Addition)
pp. 1
Reaction with Trichloromethanesulfonyl Chloride
pp. 1
Chemoselective Substitution of Heteroatoms
pp. 1
Reactions with Steroids
pp. 1
Synthesis by Regioselective Addition to the Carbon Skeleton
pp. 1
Using Hydrogen Chloride
pp. 1
Synthesis Using Chlorotrimethylsilane
pp. 1
Reactions of Iodoalkanes with Hypervalent Iodo Compounds
pp. 1
Hydrochlorination of Aziridines Using Other Metal Chlorides
pp. 1
[2+4]-Cycloaddition Reactions
pp. 1
Hydrobromination of Tetrahydrofurans and Oxetanes
pp. 1
Reactions with Manganese(III) Acetate and Lithium Chloride
pp. 1
(Dichloroiodo)benzene as Chlorine-Atom Donor
pp. 1
Synthesis by Bromination of Thiiranes
pp. 1
Hydroiodination of Aziridines Using Hydrogen Iodide
pp. 1
Synthesis from Bromoalkynes by Hydrogenation
pp. 1
Synthesis from Amines via Diazonium Salts
pp. 1
Alkane Functionalization in the Presence of -Butyl Hypoiodite
pp. 1
Direct Iodination of the Tetrahydropyran-2-yloxy Group
pp. 1
Hydrobromination of Aziridines Using Tetraalkylammonium Bromides
pp. 1
Replacement of an Alcoholic Hydroxy Group with Selenium Tetrachloride
pp. 1
With 1-Chloro-,,2-trimethylprop-1-enylamine
pp. 1
Catalyzed by Lewis Acids
pp. 1
Reaction of Alcohols with Bromotrimethylsilane
pp. 1
Synthesis from Haloalkanes with Hydriodic Acid
pp. 1
Synthesis by Substitution of σ-Bonded Heteroatoms
pp. 1
Bromodecarboxylation of Thallium(I) Carboxylates
pp. 1
Reaction with -Chloro--cyclohexylbenzenesulfonamide
pp. 1
Reaction with Bromomalonates
pp. 1
Using Sodium Chloride
pp. 1
Reaction with Trichloromethanesulfonyl Bromide
pp. 1
Brominating Reagents Containing a C—Br Bond
pp. 1
Activation with Phosphine Reagents
pp. 1
Iodohydrins Using Hypervalent Iodine Compounds
pp. 1
Substitution of Alcohols with Isomerization
pp. 1
Reaction with Trichloromethyl Chloroformate or Bis(trichloromethyl) Carbonate
pp. 1
[2+3]-Cycloaddition Reactions
pp. 1
Hydroiodination of Epoxides Using Magnesium Iodide
pp. 1
Iodination in Ionic Liquids
pp. 1
Reactions of Chloroalkanes with Metal Bromides and a Phase-Transfer Catalyst
pp. 1
Reaction with a Vilsmeier Reagent and Hydrogen Peroxide
pp. 1
Benzylic Chlorides from Benzylic Alcohols
pp. 1
Synthesis from Alkylamines via Formation of Trialkylammonium Salts
pp. 1
Hydrobromination of Aziridines with Bromotrimethylsilane
pp. 1
Aldehydes and Ketones
pp. 1
Alkylation of Arenes with 1,2-Dibromo-1-ethoxyethane
pp. 1
Chlorodecarboxylation in the Presence of Lithium Chloride
pp. 1
Reactions with Trichloromethanesulfonyl Chloride
pp. 1
Replacement of an Alcoholic Hydroxy Group with -Butyl Chloride in an Ionic Liquid
pp. 1
Using Phosphorus Tribromide on Silica Gel
pp. 1
With -Chlorosuccinimide and Dimethyl Sulfide
pp. 1
Photochemical Iodination at the Benzylic Position
pp. 1
Bromotrichloromethane as Bromine-Atom Donor
pp. 1
Hydrochlorination of Epoxides Using Elemental Chlorine
pp. 1
Coupling Reactions
pp. 1
Preparation of 4-Chlorobuta-1,2-diene from But-1-en-3-yne
pp. 1
Chlorination Using Hydrochloric Acid, Calcium Chloride, Copper(I) Chloride, and Copper Metal
pp. 1
Synthesis from Organozinc Reagents
pp. 1
Substitution of Chlorine
pp. 1
Using Chlorine
pp. 1
Synthesis by Heteroatom Substitution
pp. 1
Reaction of Alcohols with Hydrobromic Acid/Sulfuric Acid
pp. 1
Synthesis via Hydrozirconation
pp. 1
Ethers
pp. 1
Hydrochlorination of Aziridines Using Hydrogen Chloride
pp. 1
Synthesis from Organostannane Compounds
pp. 1
Chlorination Reagents Containing an I—Cl Bond
pp. 1
Activation with Phosphite Esters or Phosphorus Amides
pp. 1
Chlorination of Alkenes
pp. 1
Using Calcium Chloride
pp. 1
Reaction with Carbon Tetrabromide
pp. 1
Chlorination with (Dichloroiodo)arenes
pp. 1
Azido- and Aminoiodination of Alkenes
pp. 1
Synthesis from Propargylic Alcohols and 1-Chloro-,,2-trimethylprop-1-en-1-amine
pp. 1
Reaction of Alcohols with Polymer-Bound Phosphorus Tribromide
pp. 1
Synthesis from -Alkyl--tosylhydrazines
pp. 1
Reaction with Benzenesulfonyl Chloride
pp. 1
Hydroiodination of Aziridines Using Iodotrimethylsilane
pp. 1
Iodomethylation of an Arene Using Chloromethyl Methyl Ether and Hydrogen Iodide
pp. 1
Synthesis from Bromoalkenes
pp. 1
Chlorodecarboxylation of Carboxylic Acids by Lead(IV) Acetate
pp. 1
Reaction with 4-Bromo-2,4,6-tri--butylhexa-2,5-dienone
pp. 1
Reactions with Isoprenoids
pp. 1
Synthesis by Substitution of σ-Bonded Heteroatoms
pp. 1
Reaction with Chlorine
pp. 1
Synthesis from Chlorocarbenes
pp. 1
Chlorodecarboxylation of the Heavy Metal Salts of Carboxylic Acids
pp. 1
Synthesis from Organo-Group 15 Derivatives
pp. 1
Replacement of an Alcoholic Hydroxy Group with Thionyl Chloride
pp. 1
Substitution of Hydroxy Groups
pp. 1
Chloroalkylation of Arenecarbaldehydes Using Alkylboron Dichlorides in the Presence of Oxygen
pp. 1
Replacement of an Alcoholic Hydroxy Group with Chloromethylenedimethyliminium Chloride and Related Reagents
pp. 1
Reaction with Liquid Chlorine
pp. 1
Synthesis from Mercury(II) Carboxylates of Aliphatic Acids
pp. 1
Using Triphenylphosphine/2,3-Dichloro-5,6-dicyanobenzo-1,4-quinone and a Quaternary Ammonium Chloride
pp. 1
Replacement of an Alcoholic Hydroxy Group via Oxyphosphonium Intermediates
pp. 1
Hydrochlorination of Aziridines Using Activated Dimethylformamide Complexes
pp. 1
Using an Inorganic Support
pp. 1
Hydrobromination of Aziridines Using Alkali Metal Bromides
pp. 1
Aminochlorination of Alkenes
pp. 1
Using Triphenylphosphine and Tetrachloromethane
pp. 1
Synthesis from Alkylamines via Pyrolysis of 1-Alkylpyridinium Salts
pp. 1
Chlorination Reagents Containing an O—Cl Bond
pp. 1
Replacement of an Alcoholic Hydroxy Group with Hydrogen Chloride or a Metal Halide
pp. 1
Hydroiodination of Aziridines Using Indium(III) or Zinc(II) Iodide
pp. 1
Reaction with Trichloroacetyl Chloride, Chloroacetyl Chloride, Benzoyl Chloride, or Ethyl Chloroformate
pp. 1
Cleavage of Esters or Amides of Mononuclear Oxyacids of Phosphorus
pp. 1
Hydrochlorination of Epoxides Using Cerium(III) Chloride
pp. 1
Reactions with -Chlorosuccinimide
pp. 1
Activation with Diazolides
pp. 1
With Chlorotrimethylsilane in the Presence of Bismuth(III) Chloride
pp. 1
With Methanesulfonyl Chloride
pp. 1
Bromodecarboxylation of Carboxylic Acids
pp. 1
Synthesis from Alkanesulfonates and a Source of Chloride Ion
pp. 1
Iodocyclization of Enols
pp. 1
Synthesis Using Carbon Tetrachloride
pp. 1
Synthesis of Product Subclass 2
pp. 1
Hydroiodination of Methylenecyclopropanes
pp. 1
By Polymerization
pp. 1
Alkanes and Cycloalkanes
pp. 1
Cleavage of Alkyl Ethers
pp. 1
Hydrochlorination of Epoxides Using Chloro(imido)metal Complexes
pp. 1
Via Hydroboration
pp. 1
Carboxylic Acids and Derivatives
pp. 1
Hydrochlorination of Aziridines Using Alkali Metal Chlorides
pp. 1
Iodination of Alkenes
pp. 1
Synthesis from Haloalkanes with Iodosilanes
pp. 1
Hydrobromination of Epoxides Using Lithium Tetrabromonickelate(II)
pp. 1
Iodination with Iodosilane Reagents
pp. 1
Hydroiodination of Epoxides Using Elemental Iodine
pp. 1
Chlorination of Arenes
pp. 1
Synthesis from Compounds of the Alkali or Alkaline Earth Metals
pp. 1
Hydrobromination of Cyclopropanes
pp. 1
Using Titanium(IV) Bromide
pp. 1
In the Presence of Excess Triethylamine
pp. 1
Synthesis Using Silica Chloride
pp. 1
Chlorodecarboxylation of 1-(Acyloxy)pyridine-2(1)-thiones
pp. 1
Using Paraformaldehyde and Hydrogen Bromide
pp. 1
Chloromethylation with Chloromethyl Methyl Ether or Bis(chloromethyl) Ether
pp. 1
Enantioselective Hydrochlorination Reactions
pp. 1
Amines
pp. 1
Synthesis by Electrochemical Chlorination
pp. 1
Reactions with Halogenated -Bromoacetamides
pp. 1
Alcohols
pp. 1
Using Hydrogen Bromide
pp. 1
Hydrochlorination of Epoxides Using Niobium(V) Chloride
pp. 1
Hydroiodination of Aziridines Using Other Metal Iodides
pp. 1
Using Triphenylphosphine and Dichloroselenuranes
pp. 1
Nucleophilic Substitution in Ionic Liquids
pp. 1
Hydroiodination of Epoxides Using Hydrogen Iodide
pp. 1
Reaction with Allyl(trimethyl)silane
pp. 1
Hydrobromination of Aziridines Using Hydrogen Bromide
pp. 1
With Dimethyl Sulfoxide
pp. 1
Cleavage with Hydriodic Acid
pp. 1
Hydrochlorination of Epoxides Using Phosphorus Chlorides, Phosphonium Chlorides, Thionyl Chloride, and Related Compounds
pp. 1
Decarbonylation of Acyl Bromides
pp. 1
Hydrobromination of Aziridines Using Benzyl Bromides
pp. 1
Ring-Opening Reactions of Cyclobutanones
pp. 1
Enantioselective Hydroiodination of Epoxides Using Trialkylazidosilanes and Allyl Iodide
pp. 1
Reaction with Copper(II) Bromide
pp. 1
Synthesis from Chloroalkenes
pp. 1
Iodohydrins Using Hypoiodous Acid
pp. 1
Synthesis from Esters of Sulfur, Nitrogen, or Phosphorus Oxyacids
pp. 1
By Cycloaddition Reactions
pp. 1
Hydrobromination of Epoxides Using Alkali Metal Bromides
pp. 1
Decarboxylation of a Chloroformate Group
pp. 1
Hydrobromination of Epoxides Using Tin(II) Bromide
pp. 1
Hydrochlorination of Alkynes or Allenes
pp. 1
Ring Opening of Cyclopropanes Using Mercury(II) Salts and Iodine
pp. 1
Direct Iodinolysis
pp. 1
Chlorination with Sulfuryl Chloride
pp. 1
Reaction of 1-Cyclopropylalkan-1-ols with Magnesium Bromide
pp. 1
Bromochlorination of Alkenes
pp. 1
With Tellurium Dioxide
pp. 1
Reaction of 1-Cyclopropylalkan-1-ols with Bromotrimethylsilane–Zinc(II) Bromide
pp. 1
Azidobromination of Alkenes
pp. 1
Chlorination with Chlorine Monoxide
pp. 1
Carbobromination
pp. 1
Synthesis from Aliphatic Peroxyacids and Hydroperoxides by Degradation
pp. 1
Bromocyclization
pp. 1
Reaction with Bromine in the Absence of a Catalyst
pp. 1
Reaction with Sodium Bromide and Hydrogen Peroxide
pp. 1
Reaction of Alcohols with Triphenylphosphine–Bromine
pp. 1
Isocyanates and Isothiocyanates
pp. 1
Synthesis from Organosilicon Compounds
pp. 1
Hydrobromination of Aziridines Using Other Metal Bromides
pp. 1
Synthesis by Regioselective Substitution of Heteroatoms
pp. 1
Synthesis from Iodoalkynes
pp. 1
Using Phosphorus Pentachloride
pp. 1
Hydrobromination of Epoxides Using Hydrogen Bromide
pp. 1
Synthesis from Organoboranes or Organoaluminum Compounds
pp. 1
Synthesis from -Alkyl-Substituted Amides
pp. 1
Chloroalkylation Reactions
pp. 1
Synthesis from Aliphatic Carbonyl Compounds or Acetals
pp. 1
Reactions with Unsaturated Esters, Nitriles, and Heterocycles
pp. 1
Carbochlorination
pp. 1
Chlorination Using Gaseous Hydrogen Chloride
pp. 1
Hydroiodination of 1,3-Dienes
pp. 1
Hydrochlorination of Unsymmetrical Alkenes and Cycloalkenes (anti-Markovnikov Addition)
pp. 1
In the Absence of Catalyst
pp. 1
Modification of the Carbon Skeleton
pp. 1
Reaction with Sulfuryl Chloride and a Catalyst
pp. 1
Reaction of Alcohols with Triphenylphosphine–-Bromosuccinimide
pp. 1
By Isomerization Reactions
pp. 1
Using Hydrochloric Acid or Hydrogen Chloride
pp. 1
Hydrobromination of Alkynes or Allenes
pp. 1
Synthesis from Alkyl Xanthates (-Alkyldithiocarbonates) or from Thionocarbonates (,-Dialkylthiocarbonates)
pp. 1
Benzylic Chlorides from Other Benzylic Halides
pp. 1
In the Presence of Dimethyl Sulfoxide
pp. 1
Addition of Chlorodimethylsilane to Ketones
pp. 1
Chloromethylation with Formaldehyde and Hydrogen Chloride
pp. 1
Synthesis from -(Acyloxy)pyridine-2(1)-thiones by Degradation
pp. 1
Elimination of Benzeneseleninic Acid
pp. 1
Synthesis from Propargylic Alcohols and Hydrochloric Acid
pp. 1
Substitution of Acyloxy Groups in Carboxylic Esters
pp. 1
Cleavage of Ammonioalkanesulfonate Esters
pp. 1
Reaction with 3-Methylimidazolium Tribromide
pp. 1
Intermolecular Addition
pp. 1
Synthesis from Haloalkanes by Iodide-Catalyzed Exchange Reactions
pp. 1
Cleavage of Silyl Ethers
pp. 1
Aldehydes
pp. 1
Allylic Bromination Using -Bromosuccinimide
pp. 1
Reactions with Phosphorus Pentachloride
pp. 1
With Carbon Tetrachloride or Hexachloroacetone and Triphenylphosphine
pp. 1
Using Lithium Chloride
pp. 1
Using Tetraalkylammonium Chlorides
pp. 1
Synthesis from Lead(IV) Salts of Aliphatic Acids
pp. 1
By Hydrogenation
pp. 1
By Bromoalkylation
pp. 1
Using Tin(IV) Chloride
pp. 1
Synthesis from Aliphatic Acids by Decarboxylation with Hypervalent Iodine Compounds
pp. 1
Cleavage with Carboxylic Acid Iodides
pp. 1
Ring-Expanded Iodides by Wagner–Meerwein Rearrangement
pp. 1
Chlorodecarboxylation in the Presence of -Chlorosuccinimide
pp. 1
Reactions with Lewis Acids
pp. 1
Hydrobromination of Epoxides Using Lithium Tetrabromocuprate(II)
pp. 1
Synthesis from Chloro- or Bromoalkanes with Alkali Metal Iodides
pp. 1
Bromination of Aromatic Compounds
pp. 1
Reactions of Chloroalkanes with Gaseous Hydrogen Bromide in the Presence of Iron(III) Bromide
pp. 1
Haloalkanes and Halocycloalkanes
pp. 1
Alkane Functionalization with Iodine in the Presence of Aluminum Triiodide and Tetrahalomethanes
pp. 1
Substitution of Iodine
pp. 1
Using Triphenylphosphine and Cyclic -Chloroimides
pp. 1
Reactions of Iodoalkanes with Bromine
pp. 1
Substitution of Bromine or Iodine
pp. 1
Carboiodination
pp. 1
Allylic Bromination Using Bromine
pp. 1
Synthesis from Iodoalkanes
pp. 1
Synthesis by Deoxidative Halogenation of Ketones
pp. 1
Replacement of an Alcoholic Hydroxy Group with Chlorotrimethylsilane
pp. 1
Reaction of Carboxylic Esters with Triphenylphosphine–Bromine
pp. 1
Chloroalkanes from Alkyl Phenyl Tellurides
pp. 1
Decarboxylation of Chloroformates
pp. 1
Reaction of Chloroalkanes with Aqueous Hydrogen Bromide
pp. 1
Bromination of Alkenes
pp. 1
Activation with Onium Salts of 2-Fluoroazaarenes
pp. 1
Synthesis from Alkyl Sulfides via Formation of Sulfonium Salts
pp. 1
Hydrobromination of Epoxides Using Phosphorus Tribromide or Phosphonium Bromides
pp. 1
Synthesis from Trialkylboranes
pp. 1
Iodination with Hydriodic Acid
pp. 1
Synthesis from Ethers
pp. 1
Using Phosphoryl Chloride
pp. 1
Using Other Reagents
pp. 1
Iodination with Phosphorus and Iodine or with Phosphorus Triiodide
pp. 1
Miscellaneous Reactions
pp. 1
Using Paraformaldehyde, Hydrogen Bromide, and Ultrasound
pp. 1
Bromodecarboxylation of Carboxylic Acids with (Diacetoxyiodo)benzene and Bromine
pp. 1
Cleavage of an Acyloxy, Formyloxy, or Carbamate Group with Iodotrimethylsilane
pp. 1
Hydrochlorination of Epoxides Using Organoaluminum Chlorides
pp. 1
Iodination with Metal Iodides and Acid as a Source of Hydriodic Acid
pp. 1
By Iodoalkylation Reactions
pp. 1
Reaction of Silyl Ethers with Triphenylphosphine/2,4,4,6-Tetrabromocyclohexa-2,5-dienone
pp. 1
Cleavage of a Trimethylsiloxy Group
pp. 1
Synthesis via Hydroboration
pp. 1
Fluorochlorination of Alkenes
pp. 1
Generation of Electrophilic Bromine by In Situ Oxidation of Bromide
pp. 1
Bromination with -Bromosuccinimide
pp. 1
Hydroiodination of Epoxides Using Phosphorus Iodides and Phosphonium Iodides
pp. 1
Bromodecarboxylation of Carboxylic Acids in the Presence of Mercury(II) Oxide
pp. 1
Reaction of 1-Cyclopropylalkan-1-ols with Hydrogen Bromide
pp. 1
Reactions with Hypohalites
pp. 1
Reaction with Pyridinium Tribromide
pp. 1
Bromomethylation of Arenes
pp. 1
Reaction of Methanesulfonates with Metal Bromides
pp. 1
Hydrochlorination of Epoxides Using Hydrogen Chloride
pp. 1
Reaction with Aqueous Hydrogen Bromide
pp. 1
Hydrochlorination of Epoxides Using Chloroorganostannanes
pp. 1
Hydroiodination of Aziridines Using Samarium(II) Iodide
pp. 1
Hydrochlorination of Unsymmetrical Alkenes and Cycloalkenes (Markovnikov Addition)
pp. 1
Synthesis by Iodination of Thiiranes
pp. 1
Reactions with Aliphatic and Alicyclic Alkenes
pp. 1
Iodosulfonation of Alkenes
pp. 1
Reaction with -Bromosuccinimide
pp. 1
Bromination of Pentafluoro(vinyl)cyclopropanes
pp. 1
Iodination with Metal Iodides
pp. 1
Conversion of Natural and Synthetic Rubbers
pp. 1
Using Triphenylphosphine, Diethyl Azodicarboxylate, and Zinc(II) Chloride
pp. 1
Using Hydrogen Bromide and a Radical Source
pp. 1
Iodine Trichloride as Chlorine-Atom Donor
pp. 1
Activation with Metal-Containing Lewis Acids
pp. 1
Cleavage of Dialkyl Sulfates
pp. 1
Hydrobromination of Epoxides Using Bromo(imido)metal Complexes
pp. 1
Synthesis from Bromoalkanes
pp. 1
Synthesis from Aliphatic Acids by Decarboxylation with Organic Peroxides
pp. 1
Oxychlorination of Alkenes
pp. 1
Allylic Chlorides from Allylic Alcohols
pp. 1
Synthesis from Aliphatic Carboxylic Acid Esters
pp. 1
Intermolecular Additions
pp. 1
Reaction with Benzyltrimethylammonium Tetrachloroiodate
pp. 1
Hydrochlorination of Epoxides Using Alkali Metal Chlorides
pp. 1
Intramolecular Cyclization
pp. 1
Hydrobromination of Unsymmetrical Alkenes (anti-Markovnikov Addition)
pp. 1
Reaction of Alcohols with Aqueous Hydrobromic Acid
pp. 1
Hydrochlorination of Epoxides Using Titanium(IV) Chloride
pp. 1
Chlorination with Phosphorus Pentachloride
pp. 1
Via Hydrozirconation
pp. 1
Synthesis from Aliphatic Esters or Acid Chlorides by O-Silylation
pp. 1
Bromoalkanes from Organo-Group 15 Derivatives
pp. 1
In an Inert Solvent in the Absence of a Base
pp. 1
Hydrochlorination of Symmetrical Alkenes and Cycloalkenes
pp. 1
Iodochlorination of Alkenes
pp. 1
Synthesis with Aqueous Hydrogen Chloride
pp. 1
Selenochlorination of Alkenes
pp. 1
Reaction with Bromine in the Presence of a Catalyst
pp. 1
Reaction with Iodomethane
pp. 1
Decarbonylation of Acyl Chlorides
pp. 1
Hydrochlorination of Methylenecyclopropanes
pp. 1
Synthesis under Phase-Transfer Conditions
pp. 1
Hydrochlorination of Epoxides Using Chlorocarbonylated Compounds
pp. 1
Preparation of Bromoalkanes from Alcohols by a Modified Mitsunobu Procedure
pp. 1
Reaction with Phosphoryl Chloride
pp. 1
Allylic Chlorides from Other Allylic Halides
pp. 1
Iodine Transfer from Organic or Organometallic Iodides
pp. 1
Reaction with -Chlorosuccinimide
pp. 1
Cleavage with Alkali Metal Iodides and Acids
pp. 1
Using Phase-Transfer Conditions
pp. 1
Iodohydrins Using -Iodosuccinimide
pp. 1
Hydrochlorination of Epoxides Using Tetraalkylammonium Chlorides
pp. 1
Synthesis from Alkylamines via Formation of -Alkyl-,-disulfonylamines
pp. 1
Synthesis of 1-Chloro-3-methylbut-2-ene Using Thionyl Chloride/Silica Gel
pp. 1
By Insertion of Methylene into C—Cl Bonds
pp. 1
Hydrochlorination of Cyclopropanes
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