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Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 38

Peroxides
Georg Thieme Verlag KGerschienen am01.07.2014

Science of Synthesis: Houben-Weyl Methods of Molecular Transformations is the entirely new edition of the acclaimed reference series Houben-Weyl, the standard synthetic chemistry resource since 1909. This new edition is published in English and will comprise 48 volumes published between the years 2000 and 2008.

Science of Synthesis is a quality reference work developed by a highly esteemed editorial board to provide a comprehensive and critical selection of reliable organic and organometallic synthetic methods. This unique resource is designed to be the first point of reference when searching for a synthesis strategy.
Contains the expertise of presently 400 leading chemists worldwide Critically evaluates the preparative applicability and significance of the synthetic methods Discusses relevant background information and provides detailed experimental procedures
For full information on the Science of Synthesis series, visit the Science of Synthesis Homepagemehr
Verfügbare Formate
EUR2.589,99

Produkt

Klappentext
Science of Synthesis: Houben-Weyl Methods of Molecular Transformations is the entirely new edition of the acclaimed reference series Houben-Weyl, the standard synthetic chemistry resource since 1909. This new edition is published in English and will comprise 48 volumes published between the years 2000 and 2008.

Science of Synthesis is a quality reference work developed by a highly esteemed editorial board to provide a comprehensive and critical selection of reliable organic and organometallic synthetic methods. This unique resource is designed to be the first point of reference when searching for a synthesis strategy.
Contains the expertise of presently 400 leading chemists worldwide Critically evaluates the preparative applicability and significance of the synthetic methods Discusses relevant background information and provides detailed experimental procedures
For full information on the Science of Synthesis series, visit the Science of Synthesis Homepage
Details
Weitere ISBN/GTIN9783131721518
ProduktartE-Book
EinbandartE-Book
FormatPDF
Erscheinungsjahr2014
Erscheinungsdatum01.07.2014
Seiten582 Seiten
SpracheEnglisch
Dateigrösse7830
Artikel-Nr.1551551
Rubriken
Genre9200

Inhalt/Kritik

Inhaltsverzeichnis
1;Science of Synthesis - Volume 38: Peroxides;1
1.1;Title page;3
1.2;Imprint;5
1.3;Preface;6
1.4;Overview;8
1.5;Table of Contents;10
1.6;Introduction;28
1.7;38.1 Product Class 1: Alkyl and Cycloalkyl Hydroperoxides;36
1.7.1;38.1.1 Product Subclass 1: a-Unsubstituted Alkyl Hydroperoxides;36
1.7.1.1;38.1.1.1 Synthesis of Product Subclass 1;37
1.7.1.1.1;38.1.1.1.1 Method 1: Reactions of Alkanes with Molecular Oxygen;37
1.7.1.1.2;38.1.1.1.2 Method 2: Hydrolysis of Alkyl Metal and Alkyl Metalloid Peroxides;38
1.7.1.1.2.1;38.1.1.1.2.1 Variation 1: Via Oxidation of Alkylmagnesium Halides with Molecular Oxygen;38
1.7.1.1.2.2;38.1.1.1.2.2 Variation 2: Via Oxidation of Alkylboron Halides with Molecular Oxygen;39
1.7.1.1.3;38.1.1.1.3 Method 3: Reaction of Oxetanes with Hydrogen Peroxide;40
1.7.1.1.4;38.1.1.1.4 Method 4: Reaction of Epoxides with Hydrogen Peroxide;41
1.7.1.1.4.1;38.1.1.1.4.1 Variation 1: Catalyzed by Methyltrioctylammonium Tetrakis(oxodiperoxotungsto)phosphate;42
1.7.1.1.5;38.1.1.1.5 Method 5: Reaction of Alkyl Halides;43
1.7.1.1.5.1;38.1.1.1.5.1 Variation 1: With Hydrogen Peroxide in the Presence of Silver(I) Trifluoroacetate;43
1.7.1.1.5.2;38.1.1.1.5.2 Variation 2: With 2-Alkoxypropan-2-yl and 2-(2-Methoxyethoxy)propan-2-yl Hydroperoxides;44
1.7.1.1.5.3;38.1.1.1.5.3 Variation 3: With Potassium Superoxide;45
1.7.1.1.6;38.1.1.1.6 Method 6: Reaction of Alcohols with Hydrogen Peroxide;46
1.7.1.1.6.1;38.1.1.1.6.1 Variation 1: Without Catalysts;46
1.7.1.1.6.2;38.1.1.1.6.2 Variation 2: With Acid Catalysis;47
1.7.1.1.7;38.1.1.1.7 Method 7: Reaction of Dialkyl Sulfates with Hydrogen Peroxide;47
1.7.1.1.8;38.1.1.1.8 Method 8: Reaction of Alkyl Methanesulfonates with Hydrogen Peroxide;48
1.7.1.1.8.1;38.1.1.1.8.1 Variation 1: Reaction of Homoallylic Methanesulfonates with Hydrogen Peroxide;49
1.7.1.1.8.2;38.1.1.1.8.2 Variation 2: Reaction of Cyclic Homoallylic 4-Bromobenzenesulfonates with Hydrogen Peroxide;50
1.7.1.1.9;38.1.1.1.9 Method 9: Reaction of 1-Substituted 1-Sulfonylhydrazines with Molecular Oxygen under Basic Conditions;50
1.7.1.1.10;38.1.1.1.10 Method 10: Reaction of 1-Alkyl-2-tosylhydrazines with Hydrogen Peroxide and Sodium Peroxide;51
1.7.1.1.11;38.1.1.1.11 Method 11: Synthesis from Alkenes;52
1.7.1.1.11.1;38.1.1.1.11.1 Variation 1: With Triethylsilane and Oxygen with a Cobalt(II) Catalyst;53
1.7.1.1.11.2;38.1.1.1.11.2 Variation 2: Photooxygenation with Methylene Blue Sensitizer;54
1.7.1.1.11.3;38.1.1.1.11.3 Variation 3: Photooxygenation with 4-Chlorobenzenethiol;55
1.7.1.1.11.4;38.1.1.1.11.4 Variation 4: With N-Bromosuccinimide and Hydrogen Peroxide;55
1.7.1.1.11.5;38.1.1.1.11.5 Variation 5: With 1,3-Dibromo-5,5-dimethylhydantoin and Hydrogen Peroxide;56
1.7.1.1.12;38.1.1.1.12 Method 12: Synthesis from Conjugated Dienes;57
1.7.1.1.13;38.1.1.1.13 Method 13: Synthesis from Peroxy Esters;57
1.7.1.2;38.1.1.2 Applications of Product Subclass 1 in Organic Synthesis;58
1.7.2;38.1.2 Product Subclass 2: a-Halogen-Substituted Alkyl Hydroperoxides;58
1.7.2.1;38.1.2.1 Synthesis of Product Subclass 2;59
1.7.2.1.1;38.1.2.1.1 a-Fluoroalkyl Hydroperoxides;59
1.7.2.1.1.1;38.1.2.1.1.1 Method 1: Decomposition of Hexafluoroacetone Perhydrate;59
1.7.2.1.1.2;38.1.2.1.1.2 Method 2: Reaction of Perfluoroperoxy Derivatives with Water;59
1.7.2.1.2;38.1.2.1.2 a-Chloroalkyl Hydroperoxides;60
1.7.2.1.2.1;38.1.2.1.2.1 Method 1: Reaction of Chloroalkenes with Ozone;60
1.7.3;38.1.3 Product Subclass 3: a-Oxygen-Substituted Alkyl Hydroperoxides;61
1.7.3.1;38.1.3.1 Synthesis of Product Subclass 3;61
1.7.3.1.1;38.1.3.1.1 a-Hydroxyalkyl Hydroperoxides;61
1.7.3.1.1.1;38.1.3.1.1.1 Method 1: Reaction of Aldehydes with Hydrogen Peroxide and Iodine;61
1.7.3.1.1.2;38.1.3.1.1.2 Method 2: Reaction of a-Halo Ketones with Hydrogen Peroxide;62
1.7.3.1.2;38.1.3.1.2 a-Alkoxyalkyl Hydroperoxides;63
1.7.3.1.2.1;38.1.3.1.2.1 Method 1: Ozonolysis of Alkenes;63
1.7.3.1.2.2;38.1.3.1.2.2 Method 2: Reaction of Vinyl Ethers with Ozone and Alcohols;65
1.7.3.1.2.2.1;38.1.3.1.2.2.1 Variation 1: With Hydrogen Peroxide;67
1.7.3.1.2.2.2;38.1.3.1.2.2.2 Variation 2: With Hydrogen Peroxide and Silica Gel;67
1.7.3.1.2.2.3;38.1.3.1.2.2.3 Variation 3: With Hydrogen Peroxide and Molybdenum(VI) Oxide;68
1.7.3.1.2.3;38.1.3.1.2.3 Method 3: Reaction of Dialkyl Ethers with Molecular Oxygen;69
1.7.3.1.2.4;38.1.3.1.2.4 Method 4: a-Reaction of Cyclopropyl Alcohols with Hydrogen Peroxide;69
1.7.3.1.2.5;38.1.3.1.2.5 Method 5: Reaction of Ketones and Alcohols with Hydrogen Peroxide;71
1.7.3.1.2.6;38.1.3.1.2.6 Method 6: Reaction of Hydroxy Ketones and Diketones with Hydrogen Peroxide;71
1.7.3.1.2.7;38.1.3.1.2.7 Method 7: Reaction of Ketones with Hydrogen Peroxide Catalyzed by Iodine;72
1.7.3.1.2.8;38.1.3.1.2.8 Method 8: Reaction of Homoallylic 4-Bromobenzenesulfonates and Hydrogen Peroxide;73
1.7.3.1.2.9;38.1.3.1.2.9 Method 9: Ring Opening of Oxetanes with Hydrogen Peroxide;74
1.7.3.1.3;38.1.3.1.3 a-Peroxyalkyl Hydroperoxides;74
1.7.3.1.3.1;38.1.3.1.3.1 Method 1: Reaction of Alkenes and Vinyl Ethers with Ozone;74
1.7.3.1.3.1.1;38.1.3.1.3.1.1 Variation 1: Intramolecular Reaction of Alkyl Hydroperoxides with Carbonyl Oxides Generated by Ozonolysis of Alkenes;75
1.7.3.1.3.2;38.1.3.1.3.2 Method 2: Reaction of Ketones with Hydrogen Peroxide;76
1.7.3.1.3.3;38.1.3.1.3.3 Method 3: Reaction of Acetals with Hydrogen Peroxide Mediated by Boron Trifluoride--Diethyl Ether Complex;76
1.7.3.1.3.4;38.1.3.1.3.4 Method 4: Reaction of Dialkyl Ethers with Molecular Oxygen;77
1.7.3.1.4;38.1.3.1.4 a-(Triorganosiloxy)alkyl Hydroperoxides;78
1.7.3.1.4.1;38.1.3.1.4.1 Method 1: Reaction of Trialkylsilyl Vinyl Ethers and Hydrogen Peroxide;78
1.7.3.1.5;38.1.3.1.5 a-(Acyloxy)alkyl Hydroperoxides;78
1.7.3.1.5.1;38.1.3.1.5.1 Method 1: Photooxidation of an Enol Lactone;78
1.7.3.1.6;38.1.3.1.6 1,1-Bis(hydroperoxy)alkanes;79
1.7.3.1.6.1;38.1.3.1.6.1 Method 1: Reaction of Ketones with Hydrogen Peroxide with Acid Catalysts;79
1.7.3.1.6.1.1;38.1.3.1.6.1.1 Variation 1: With 1,2-Bis(diphenylphosphoryl)ethane;80
1.7.3.1.6.1.2;38.1.3.1.6.1.2 Variation 2: Catalyzed by Ammonium Cerium(IV) Nitrate;81
1.7.3.1.6.1.3;38.1.3.1.6.1.3 Variation 3: Catalyzed by Methyltrioxorhenium(VII) in Trifluoroethanol;82
1.7.3.1.6.1.4;38.1.3.1.6.1.4 Variation 4: Catalyzed by Molecular Iodine;82
1.7.3.1.6.1.5;38.1.3.1.6.1.5 Variation 5: Catalyzed by Tungstic Acid;83
1.7.3.1.6.2;38.1.3.1.6.2 Method 2: Reaction of Tosylhydrazones with Hydrogen Peroxide;84
1.7.3.1.6.3;38.1.3.1.6.3 Method 3: Reaction of Vinyl Ethers with Ozone and Hydrogen Peroxide;85
1.7.3.1.6.4;38.1.3.1.6.4 Method 4: Reaction of Ketals with Hydrogen Peroxide;86
1.7.3.1.6.5;38.1.3.1.6.5 Method 5: Ring Opening of Bicyclic Benzyl Alcohols with Hydrogen Peroxide;87
1.7.3.2;38.1.3.2 Applications of Product Subclass 3 in Organic Synthesis;87
1.7.4;38.1.4 Product Subclass 4: a-Sulfur-Substituted Alkyl Hydroperoxides;88
1.7.4.1;38.1.4.1 Synthesis of Product Subclass 4;88
1.7.4.1.1;38.1.4.1.1 Method 1: Photooxidation of Thiazolidines with Molecular Oxygen in the Presence of Tetraphenylphorphyrin;88
1.7.5;38.1.5 Product Subclass 5: a-Nitrogen-Substituted Alkyl Hydroperoxides;88
1.7.5.1;38.1.5.1 Synthesis of Product Subclass 5;89
1.7.5.1.1;38.1.5.1.1 a-Aminoalkyl Hydroperoxides;89
1.7.5.1.1.1;38.1.5.1.1.1 Method 1: Reaction of Carbonyl Compounds with Ammonia or Amines and Hydrogen Peroxide;89
1.7.5.1.2;38.1.5.1.2 a-(Acylamino)alkyl Hydroperoxides;91
1.7.5.1.2.1;38.1.5.1.2.1 Method 1: Reaction of Cyclic Amides and N-Alkylamides with Oxygen;91
1.7.5.1.2.2;38.1.5.1.2.2 Method 2: Reaction of N-Heterocycles with Hydrogen Peroxide;91
1.7.5.1.3;38.1.5.1.3 a-Hydrazinoalkyl Hydroperoxides;92
1.7.5.1.3.1;38.1.5.1.3.1 Method 1: Oxidation of Hydrazoalkanes;92
1.7.5.1.4;38.1.5.1.4 a-(N-Alkyl-N-nitrosoamino)alkyl Hydroperoxides;92
1.7.5.1.4.1;38.1.5.1.4.1 Method 1: Reaction of Dialkylnitrosamines with Lithium Diisopropylamide and Oxygen;92
1.7.5.1.4.2;38.1.5.1.4.2 Method 2: Reaction of 1-Acetoxyalkyl(alkyl)nitrosamines with Hydrogen Peroxide;93
1.7.5.1.5;38.1.5.1.5 4-Hydroperoxy-1,3,2-oxazaphosphorinane 2-Oxides;94
1.7.5.1.5.1;38.1.5.1.5.1 Method 1: Reaction of 4-Hydroxy-1,3,2-oxazaphosphorinane 2-Oxides with Hydrogen Peroxide;94
1.7.5.1.5.2;38.1.5.1.5.2 Method 2: Reaction of a Phosphoric Amide Diester Bearing O- or N-Alkenyl Residues and Ozone;94
1.7.5.2;38.1.5.2 Applications of Product Subclass 5 in Organic Synthesis;95
1.8;38.2 Product Class 2: Allylic Hydroperoxides;100
1.8.1;38.2.1 Synthesis of Product Class 2;105
1.8.1.1;38.2.1.1 Method 1: Synthesis from Alkenes;105
1.8.1.1.1;38.2.1.1.1 Variation 1: With Triplet Dioxygen;105
1.8.1.1.2;38.2.1.1.2 Variation 2: With Singlet Dioxygen;107
1.8.1.2;38.2.1.2 Method 2: Synthesis from Arenes;120
1.8.1.2.1;38.2.1.2.1 Variation 1: Reaction with Dioxygen under Basic Conditions;120
1.8.1.2.2;38.2.1.2.2 Variation 2: Reaction with Triplet Dioxygen in the Presence of Transition Metal Compounds;122
1.8.1.2.3;38.2.1.2.3 Variation 3: Reaction with Singlet Dioxygen;123
1.8.1.3;38.2.1.3 Method 3: Synthesis from Allylic Halides;125
1.8.1.3.1;38.2.1.3.1 Variation 1: Reaction with Hydrogen Peroxide;125
1.8.1.4;38.2.1.4 Method 4: Synthesis from Allyl Sulfonates;126
1.8.1.4.1;38.2.1.4.1 Variation 1: Reaction with Hydrogen Peroxide;126
1.8.1.5;38.2.1.5 Method 5: Synthesis from Endoperoxides;127
1.8.1.5.1;38.2.1.5.1 Variation 1: Reaction with Nucleophiles;127
1.8.1.6;38.2.1.6 Method 6: Synthesis from Allyl Hydroperoxides;128
1.8.1.6.1;38.2.1.6.1 Variation 1: Via Rearrangement;128
1.8.1.6.2;38.2.1.6.2 Variation 2: Separation of Racemates via HPLC;129
1.8.1.6.3;38.2.1.6.3 Variation 3: Enzymatic Kinetic Resolution of Racemates;130
1.9;38.3 Product Class 3: Benzylic Hydroperoxides;136
1.9.1;38.3.1 Synthesis of Product Class 3;137
1.9.1.1;38.3.1.1 Method 1: Synthesis from Aryl- or Hetarylalkanes with Retention of the Carbon Skeleton;139
1.9.1.1.1;38.3.1.1.1 Variation 1: Autoxidation;139
1.9.1.1.2;38.3.1.1.2 Variation 2: Reaction with Dioxygen in the Presence of Metal Ions;144
1.9.1.1.3;38.3.1.1.3 Variation 3: Reaction with Dioxygen in the Presence of Bases;145
1.9.1.1.4;38.3.1.1.4 Variation 4: Reaction with Dioxygen in the Presence of N-Hydroxyphthalimide;146
1.9.1.1.5;38.3.1.1.5 Variation 5: Reaction with tert-Butyl Hydroperoxide and a Transition-Metal Catalyst;146
1.9.1.1.6;38.3.1.1.6 Variation 6: Reaction with Dioxygen in the Presence of Photochemically Excited Electron-Transfer Reagents;147
1.9.1.2;38.3.1.2 Method 2: Synthesis from Arylalkanes in Combination with C--C Bond Cleavage;148
1.9.1.2.1;38.3.1.2.1 Variation 1: Photochemically Induced Reaction;148
1.9.1.3;38.3.1.3 Method 3: Synthesis from Alkenes;149
1.9.1.3.1;38.3.1.3.1 Variation 1: With Triplet Dioxygen in the Presence of Thiols;149
1.9.1.3.2;38.3.1.3.2 Variation 2: Reaction with Triplet Dioxygen in the Presence of Cobalt(II) Compounds and Silanes;149
1.9.1.3.3;38.3.1.3.3 Variation 3: Reaction with Triplet Dioxygen and Boranes;150
1.9.1.3.4;38.3.1.3.4 Variation 4: Via Electron-Transfer Processes;151
1.9.1.3.5;38.3.1.3.5 Variation 5: Reaction with Singlet Dioxygen;152
1.9.1.3.6;38.3.1.3.6 Variation 6: Reaction with Hydrogen Peroxide and Mercury(II) Salts;152
1.9.1.4;38.3.1.4 Method 4: Synthesis from Arenes;153
1.9.1.4.1;38.3.1.4.1 Variation 1: From Phenols with Dioxygen in the Absence of Catalysts;153
1.9.1.4.2;38.3.1.4.2 Variation 2: Reaction with Singlet Dioxygen;155
1.9.1.5;38.3.1.5 Method 5: Synthesis from Haloalkanes;156
1.9.1.5.1;38.3.1.5.1 Variation 1: With Hydrogen Peroxide under Acidic Conditions;156
1.9.1.5.2;38.3.1.5.2 Variation 2: With Hydrogen Peroxide under Basic Conditions;157
1.9.1.6;38.3.1.6 Method 6: Synthesis from Alcohols;157
1.9.1.6.1;38.3.1.6.1 Variation 1: By Reaction with Hydrogen Peroxide under Acidic Conditions;157
1.9.1.7;38.3.1.7 Method 7: Synthesis from Carboxylic Acid Esters;158
1.9.1.7.1;38.3.1.7.1 Variation 1: Reaction with Hydrogen Peroxide;158
1.9.1.8;38.3.1.8 Method 8: Synthesis from Ethers;159
1.9.1.8.1;38.3.1.8.1 Variation 1: Reaction of Acyclic Ethers with Hydrogen Peroxide;159
1.9.1.9;38.3.1.9 Method 9: Synthesis from Peroxy Esters;160
1.9.1.9.1;38.3.1.9.1 Variation 1: Hydrolysis in the Presence of Bis(tributyltin) Oxide;160
1.9.1.10;38.3.1.10 Method 10: Synthesis from Other Benzylic Hydroperoxides;160
1.9.1.10.1;38.3.1.10.1 Variation 1: Separation of Racemates via HPLC;160
1.9.1.10.2;38.3.1.10.2 Variation 2: Kinetic Resolution of Racemates Using Enantiopure Phosphines;161
1.9.1.10.3;38.3.1.10.3 Variation 3: Lipase-Catalyzed Kinetic Resolution of Racemates;161
1.9.1.10.4;38.3.1.10.4 Variation 4: Kinetic Resolution of Racemates Using Native Peroxidases;162
1.9.1.10.5;38.3.1.10.5 Variation 5: Enzymatic Kinetic Resolution of Racemates Using a Semisynthetic Peroxidase;164
1.9.1.10.6;38.3.1.10.6 Variation 6: Kinetic Resolution of Racemates Using Microorganisms;165
1.10;38.4 Product Class 4: Salts of Alkyl Hydroperoxides;170
1.10.1;38.4.1 Product Subclass 1: Group 15 Salts of Alkyl Hydroperoxides;171
1.10.1.1;38.4.1.1 Synthesis of Product Subclass 1;171
1.10.1.1.1;38.4.1.1.1 Method 1: Synthesis of (Alkylperoxy)antimony Compounds;171
1.10.2;38.4.2 Product Subclass 2: Group 14 Salts of Alkyl Hydroperoxides;171
1.10.2.1;38.4.2.1 Synthesis of Product Subclass 2;172
1.10.2.1.1;38.4.2.1.1 Method 1: Synthesis of (Alkylperoxy)silanes;172
1.10.2.1.1.1;38.4.2.1.1.1 Variation 1: Reaction of Silyl Enol Ethers with Singlet Oxygen;172
1.10.2.1.1.2;38.4.2.1.1.2 Variation 2: Reaction of Chlorotriorganosilanes or Triorganosilyl Trifluoromethanesulfonates with Alkyl Hydroperoxides;173
1.10.2.1.1.3;38.4.2.1.1.3 Variation 3: Reaction of N,O-Bis(triorganosilyl)acetamides with Alkyl Hydroperoxides;177
1.10.2.1.1.4;38.4.2.1.1.4 Variation 4: Reaction of .-Silyl Allylic Alcohols with Ozone;177
1.10.2.1.1.5;38.4.2.1.1.5 Variation 5: Reaction of Alkenes with Oxygen and Triethylsilane Promoted by Cobalt(II) Catalysts;178
1.10.2.1.2;38.4.2.1.2 Method 2: Synthesis of Germanium Alkyl Peroxides;180
1.10.2.1.2.1;38.4.2.1.2.1 Variation 1: Reaction of Halogermanes with Alkyl Hydroperoxides and Ammonia or Tertiary Amines;180
1.10.2.1.3;38.4.2.1.3 Method 3: Synthesis of Tin Alkyl Peroxides;181
1.10.2.1.3.1;38.4.2.1.3.1 Variation 1: Reaction of Triorganostannanes with Alkyl Hydroperoxides;181
1.10.2.1.3.2;38.4.2.1.3.2 Variation 2: Reaction of Hydroxytriorganostannanes or Oxytriorganostannanes with Alkyl Hydroperoxides;181
1.10.2.1.3.3;38.4.2.1.3.3 Variation 3: Synthesis of 1,3-Bis(alkylperoxy)-1,1,3,3-tetraorganodistannoxanes and (Alkylperoxy)(chloro)-1,1,3,3-tetraorganodistannoxanes;182
1.10.3;38.4.3 Product Subclass 3: Group 13 Salts of Alkyl Hydroperoxides;183
1.10.3.1;38.4.3.1 Synthesis of Product Subclass 3;183
1.10.3.1.1;38.4.3.1.1 Method 1: Synthesis of (Alkylperoxy)boron Compounds;183
1.10.3.1.1.1;38.4.3.1.1.1 Variation 1: Reaction of Trialkylboranes with Oxygen;183
1.10.3.1.1.2;38.4.3.1.1.2 Variation 2: Reaction of Boron Halides with Alkyl Hydroperoxides;185
1.10.3.1.1.3;38.4.3.1.1.3 Variation 3: Reaction of Tetraacetyl Diborate with Alkyl Hydroperoxides;185
1.10.3.1.1.4;38.4.3.1.1.4 Variation 4: Reaction of Alkyldichloroboranes or Chlorodicyclopentylborane with Molecular Oxygen;186
1.10.3.1.1.5;38.4.3.1.1.5 Variation 5: Oxidation of Trialkylboroxins;186
1.10.3.1.2;38.4.3.1.2 Method 2: Synthesis of Aluminum Alkyl Peroxides;187
1.10.3.1.3;38.4.3.1.3 Method 3: Synthesis of Indium Alkyl Peroxides;187
1.10.4;38.4.4 Product Subclass 4: Group 2 Salts of Alkyl Hydroperoxides;188
1.10.4.1;38.4.4.1 Synthesis of Product Subclass 4;188
1.10.4.1.1;38.4.4.1.1 Method 1: Synthesis of Magnesium Alkyl Peroxides;188
1.10.4.1.1.1;38.4.4.1.1.1 Variation 1: Reaction of Organomagnesium Halides with Oxygen;188
1.10.4.1.2;38.4.4.1.2 Method 2: Synthesis of Strontium Alkyl Peroxides;189
1.10.4.1.3;38.4.4.1.3 Method 3: Synthesis of Barium Alkyl Peroxides;189
1.10.5;38.4.5 Product Subclass 5: Group 1 Salts of Alkyl Hydroperoxides;189
1.10.5.1;38.4.5.1 Synthesis of Product Subclass 5;189
1.10.5.1.1;38.4.5.1.1 Method 1: Synthesis of Lithium Alkyl Peroxides;190
1.10.5.1.2;38.4.5.1.2 Method 2: Synthesis of Sodium Alkyl Peroxides;190
1.10.5.1.2.1;38.4.5.1.2.1 Variation 1: Reaction of Sodium tert-Butoxide with Alkyl Hydroperoxides;190
1.10.5.1.3;38.4.5.1.3 Method 3: Synthesis of Potassium Alkyl Peroxides;190
1.10.6;38.4.6 Product Subclass 6: Transition Metal Salts of Alkyl Hydroperoxides;191
1.10.6.1;38.4.6.1 Synthesis of Product Subclass 6;191
1.10.6.1.1;38.4.6.1.1 Method 1: Synthesis of Zinc Alkyl Peroxides;191
1.10.6.1.2;38.4.6.1.2 Method 2: Synthesis of Cadmium Alkyl Peroxides;191
1.10.6.1.2.1;38.4.6.1.2.1 Variation 1: Reaction of Alkylcadmium(II) Compounds with Alkyl Hydroperoxides;192
1.10.6.1.3;38.4.6.1.3 Method 3: Synthesis of Mercury Alkyl Peroxides;192
1.10.6.1.4;38.4.6.1.4 Method 4: Synthesis of Palladium Alkyl Peroxides;193
1.10.6.1.4.1;38.4.6.1.4.1 Variation 1: Reaction of Palladium(II) Carboxylates with Alkyl Hydroperoxides;193
1.10.6.1.4.2;38.4.6.1.4.2 Variation 2: Reaction of an Alkyl(bisphosphine)(hydroxy)palladium(II) Complex with an Alkyl Hydroperoxide;193
1.10.6.1.4.3;38.4.6.1.4.3 Variation 3: Reaction of (Dioxygen)bis(triphenylphosphine)palladium(II) with Electron-Deficient Alkenes;194
1.10.6.1.5;38.4.6.1.5 Method 5: Synthesis of Platinum Alkyl Peroxides;194
1.10.6.1.5.1;38.4.6.1.5.1 Variation 1: Reaction of Hydroxy(organo)bis(triorganophosphine)platinum(II) Complexes with Alkyl Hydroperoxides;194
1.10.6.1.5.2;38.4.6.1.5.2 Variation 2: Reaction of (Dioxygen)bis(triphenylphosphine)platinum(II) Complexes with Electron-Deficient Alkenes;195
1.10.6.1.5.3;38.4.6.1.5.3 Variation 3: Reaction of (Dioxygen)bis(triphenylphosphine)platinum(II) Complexes with Carbonyl Compounds;196
1.10.6.1.6;38.4.6.1.6 Method 6: Synthesis of Cobalt Alkyl Peroxides;197
1.10.6.1.6.1;38.4.6.1.6.1 Variation 1: Reaction of Organocobaloximes with Oxygen;197
1.10.6.1.6.2;38.4.6.1.6.2 Variation 2: Reaction of Cobalt(II) Complexes with Alkyl Hydroperoxides;198
1.10.6.1.6.3;38.4.6.1.6.3 Variation 3: Reaction of Cobalt(II) Complexes with Oxygen and Phenols;198
1.10.6.1.6.4;38.4.6.1.6.4 Variation 4: Reaction of Cobalt(II) Superoxo Complexes with Phenoxyl Radicals;200
1.10.6.1.7;38.4.6.1.7 Method 7: Synthesis of Iridium Alkyl Peroxide;200
1.10.6.1.8;38.4.6.1.8 Method 8: Synthesis of Titanium and Zirconium Alkyl Peroxides;201
1.10.6.1.9;38.4.6.1.9 Method 9: Synthesis of Molybdenum and Tungsten Alkyl Peroxides;201
1.10.6.1.10;38.4.6.1.10 Method 10: Synthesis of Hafnium Alkyl Peroxides;202
1.10.6.1.11;38.4.6.1.11 Method 11: Synthesis of Vanadium Alkyl Peroxides;203
1.11;38.5 Product Class 5: Alkyl and Cycloalkyl Peroxides;206
1.11.1;38.5.1 Synthesis of Product Class 5;207
1.11.1.1;38.5.1.1 Method 1: Nucleophilic Substitution;207
1.11.1.1.1;38.5.1.1.1 Variation 1: Reaction of Alkyl Hydroperoxides with Alkyl Bromides or Methanesulfonates under Basic Conditions;207
1.11.1.1.2;38.5.1.1.2 Variation 2: Reaction of Alkyl Bromides or Sulfonates with Potassium Superoxide;209
1.11.1.1.3;38.5.1.1.3 Variation 3: Phase-Transfer-Catalyzed Synthesis of Primary--Tertiary Bisperoxides;210
1.11.1.1.4;38.5.1.1.4 Variation 4: Reaction between Germanium or Tin Peroxides and Alkyl Trifluoromethanesulfonates;211
1.11.1.1.5;38.5.1.1.5 Variation 5: Acid-Catalyzed Reaction of Alkyl Hydroperoxides with Tertiary Alkyl Trichloroacetimidates;212
1.11.1.1.6;38.5.1.1.6 Variation 6: Reaction of Alkyl Hydroperoxides with Alkyl Bromides in Ionic Liquids;214
1.11.1.1.7;38.5.1.1.7 Variation 7: 1,1-Bis(alkylperoxy)alkanes via Alkylation of 1,1-Bis(hydroperoxy)alkanes;214
1.11.1.2;38.5.1.2 Method 2: Addition to a Double Bond;217
1.11.1.2.1;38.5.1.2.1 Variation 1: Acid-Catalyzed Addition of Alkyl Hydroperoxides to Enol Ethers;217
1.11.1.2.2;38.5.1.2.2 Variation 2: Base-Catalyzed Addition of Alkyl Hydroperoxides to Electron-Deficient Alkenes;218
1.11.1.2.3;38.5.1.2.3 Variation 3: Peroxymercuration of Alkenes Followed by Bromodemercuration;219
1.11.1.2.4;38.5.1.2.4 Variation 4: Cobalt-Catalyzed Triethylsilylperoxidation of Alkenes with Molecular Oxygen;220
1.11.1.3;38.5.1.3 Method 3: Peroxycarbenium-Mediated C--C Bond Formation from Monoperoxyketals and Monoperoxyacetals;221
1.11.1.3.1;38.5.1.3.1 Variation 1: Allylation of Monoperoxyketals and Monoperoxyacetals;223
1.11.1.3.2;38.5.1.3.2 Variation 2: Crotylation of Monoperoxyacetals;224
1.11.1.3.3;38.5.1.3.3 Variation 3: Synthesis of 3-Peroxy Ketones;225
1.11.1.3.4;38.5.1.3.4 Variation 4: Synthesis of 3-Peroxy Esters;226
1.11.1.4;38.5.1.4 Method 4: Opening of Oxetanes with Alkyl Hydroperoxides;226
1.11.1.5;38.5.1.5 Method 5: Opening of Epoxides with Alkyl Hydroperoxides;227
1.11.1.6;38.5.1.6 Method 6: Ruthenium-Catalyzed Oxidation of Tertiary Amines with Alkyl Hydroperoxides;228
1.11.1.7;38.5.1.7 Method 7: Epoxy Alkyl Peroxides from Allylic Alcohols Bearing an Appropriately Positioned Lactam Ring;229
1.12;38.6 Product Class 6: Allylic Peroxides;232
1.12.1;38.6.1 Synthesis of Product Class 6;232
1.12.1.1;38.6.1.1 Method 1: Nucleophilic Substitution;232
1.12.1.1.1;38.6.1.1.1 Variation 1: Reaction of Allylic Bromides with Alkyl Hydroperoxides under Basic Conditions;232
1.12.1.1.2;38.6.1.1.2 Variation 2: Alkylation of Hydroperoxyacetals under Basic Conditions;233
1.12.1.1.3;38.6.1.1.3 Variation 3: Diallylation of 1,1-Bis(hydroperoxy)alkanes under Basic Conditions;234
1.12.1.1.4;38.6.1.1.4 Variation 4: Alkylation of Allylic Hydroperoxides with an Alkyl Halide or Sulfonate under Basic Conditions;235
1.12.1.1.5;38.6.1.1.5 Variation 5: Reaction of Allylic Alcohols with tert-Butyl Hydroperoxide under Acidic Conditions;235
1.12.1.1.6;38.6.1.1.6 Variation 6: Reaction of Allylic Alcohols with tert-Butyl Hydroperoxide Catalyzed by a Polyoxometalate;236
1.12.1.1.7;38.6.1.1.7 Variation 7: Reaction of Alkyl Hydroperoxides and Tertiary Alkyl Trichloroacetimidates under Acidic Conditions;237
1.12.1.2;38.6.1.2 Method 2: Synthesis of Allylic Peroxides via Tritylation and Methoxymethylation of Allylic Stannyl Peroxides;238
1.12.1.3;38.6.1.3 Method 3: Allylic Peroxyketals via the Acid-Catalyzed Addition of Allylic Hydroperoxides to Enol Ethers;239
1.12.1.4;38.6.1.4 Method 4: Allylic Peroxidation of Alkenes with tert-Butyl Hydroperoxide;240
1.12.1.4.1;38.6.1.4.1 Variation 1: Palladium-Catalyzed Allylic Peroxidation of Cycloalkenes;240
1.12.1.4.2;38.6.1.4.2 Variation 2: Palladium/Carbon-Catalyzed Allylic Peroxidation of 1,4-Dienes;241
1.12.1.4.3;38.6.1.4.3 Variation 3: Palladium(II) Hydroxide/Carbon Catalyzed Allylic Peroxidation of Enones;242
1.12.1.4.4;38.6.1.4.4 Variation 4: Allylic Peroxidation of Cyclohexene Catalyzed by Manganese(II), Cobalt(II), Nickel(II), Copper(II), and Vanadyl Complexes Supported on Alumina;242
1.12.1.4.5;38.6.1.4.5 Variation 5: Allylic Peroxidation of Cyclohexene Catalyzed by Molybdenum Oxide and Vanadium Oxide Clusters;244
1.12.1.4.6;38.6.1.4.6 Variation 6: Allylic Peroxidation of Cycloalkenes with tert-Butyl Hydroperoxide Catalyzed by Pyridinium Chlorochromate or Pyridinium Dichromate;245
1.12.1.5;38.6.1.5 Method 5: Reaction of Conjugated Dienes and Trienes with Pyridinium Dichromate and tert-Butyl Hydroperoxide;245
1.12.1.6;38.6.1.6 Method 6: Hexacarbonylmolybdenum(0)-Catalyzed Oxidation of Enediones with tert-Butyl Hydroperoxide To Form Peroxypyranones;246
1.12.1.7;38.6.1.7 Method 7: Synthesis of Functionalized Allylic Peroxides from Allylic Peroxy Vinylstannanes;247
1.12.1.7.1;38.6.1.7.1 Variation 1: N-Iodosuccinimide-Mediated Formation of Allylic Peroxy Vinyl Iodides;248
1.12.1.7.2;38.6.1.7.2 Variation 2: Palladium-Mediated C--C Bond-Forming Reactions for the Synthesis of Functionalized Allylic Peroxides;248
1.12.1.8;38.6.1.8 Method 8: Synthesis of Allylic Peroxides via the Wittig Alkenation of a-Peroxy-Substituted Aldehydes;250
1.12.1.9;38.6.1.9 Method 9: Formation of 4-(tert-Butylperoxy)cyclohexadienones by Oxidation of Phenols;251
1.12.1.9.1;38.6.1.9.1 Variation 1: Metal-Catalyzed Oxidation of Phenols with tert-Butyl Hydroperoxide;251
1.12.1.9.2;38.6.1.9.2 Variation 2: Free-Radical Oxidation of Phenols by a Hypervalent (tert-Butylperoxy)iodane and tert-Butyl Hydroperoxide;253
1.12.1.10;38.6.1.10 Method 10: Formation of Allylic 1,4-Diperoxides from the Chloroperoxidase-Catalyzed Oxidation of Conjugated Dienoic Esters;253
1.13;38.7 Product Class 7: Benzylic Peroxides;258
1.13.1;38.7.1 Synthesis of Product Class 7;258
1.13.1.1;38.7.1.1 Oxidation with Oxygen;258
1.13.1.1.1;38.7.1.1.1 Method 1: Oxidation of Arylalkanes;258
1.13.1.1.2;38.7.1.1.2 Method 2: Oxidation of Triarylmethyl Chlorides;259
1.13.1.1.3;38.7.1.1.3 Method 3: Oxidation of Arylalkenes via Trapping Reactions;259
1.13.1.1.3.1;38.7.1.1.3.1 Variation 1: Intramolecular Cyclization in the Presence of a Cobalt(II) Complex;259
1.13.1.1.3.2;38.7.1.1.3.2 Variation 2: Intermolecular Cycloaddition with Carbonyl Compounds;260
1.13.1.1.3.3;38.7.1.1.3.3 Variation 3: Intermolecular Cyclization with ß-Oxo Carbonyl Compounds in the Presence of Manganese Catalysts;261
1.13.1.1.3.4;38.7.1.1.3.4 Variation 4: Intermolecular Cyclization with Heterocyclic 1,3-Dicarbonyl Compounds in the Presence of Manganese Catalysts;263
1.13.1.2;38.7.1.2 Oxidation with Hydroperoxides;265
1.13.1.2.1;38.7.1.2.1 Method 1: Oxidation of Arylalkanes under Metal Catalysis;265
1.13.1.2.1.1;38.7.1.2.1.1 Variation 1: Using Chromium;265
1.13.1.2.1.2;38.7.1.2.1.2 Variation 2: Using Cobalt;266
1.13.1.2.1.3;38.7.1.2.1.3 Variation 3: Using Copper;267
1.13.1.2.1.4;38.7.1.2.1.4 Variation 4: Using Lead;270
1.13.1.2.2;38.7.1.2.2 Method 2: Nucleophilic Substitution Using Hydroperoxides;271
1.13.1.2.2.1;38.7.1.2.2.1 Variation 1: Of Halides;271
1.13.1.2.2.2;38.7.1.2.2.2 Variation 2: Of Alcohols;274
1.13.1.2.2.3;38.7.1.2.2.3 Variation 3: Of Imidates;276
1.13.1.2.2.4;38.7.1.2.2.4 Variation 4: Of Oxiranes;276
1.13.1.2.3;38.7.1.2.3 Method 3: Addition Reactions of Hydroperoxides;277
1.13.1.2.3.1;38.7.1.2.3.1 Variation 1: Acid-Mediated Addition to Alkenes;277
1.13.1.2.3.2;38.7.1.2.3.2 Variation 2: Base-Mediated Addition to Alkenes;278
1.13.1.2.3.3;38.7.1.2.3.3 Variation 3: Palladium-Mediated Addition to Alkenes;279
1.13.1.2.3.4;38.7.1.2.3.4 Variation 4: Mercury-Mediated Addition to Alkenes;280
1.13.1.2.3.5;38.7.1.2.3.5 Variation 5: Addition to Cyclopropanes;281
1.13.1.2.3.6;38.7.1.2.3.6 Variation 6: Addition to Carbonyl Compounds;283
1.13.1.3;38.7.1.3 Photooxygenation;284
1.13.1.3.1;38.7.1.3.1 Method 1: Photooxygenation of Arylalkenes;284
1.13.1.3.2;38.7.1.3.2 Method 2: Photooxygenation of Three-Membered Heterocycles via Photoinduced Electron Transfer;285
1.13.1.3.3;38.7.1.3.3 Method 3: Photooxygenation of Cyclopropanes via Photoinduced Radical Production;287
1.13.1.4;38.7.1.4 Other Methods;287
1.13.1.4.1;38.7.1.4.1 Method 1: Oxidative Fluorodesulfuration;287
1.13.1.4.2;38.7.1.4.2 Method 2: Ozonization of Unsaturated Benzylic Hydroperoxides;288
1.13.1.4.3;38.7.1.4.3 Method 3: Oxygenation of Aryl Azo Hydroperoxides;289
1.13.1.4.4;38.7.1.4.4 Method 4: Acid-Catalyzed Reaction of Peroxyketals with Ketene Silyl Acetals;289
1.13.2;38.7.2 Applications of Product Class 7 in Organic Synthesis;291
1.13.2.1;38.7.2.1 Method 1: Oxidation to Carbonyl Derivatives;291
1.13.2.2;38.7.2.2 Method 2: Reduction to Alcohols;292
1.13.2.3;38.7.2.3 Method 3: Heterolysis of an O--O or C--O Bond;292
1.13.2.3.1;38.7.2.3.1 Variation 1: Trapping with Alkenes;294
1.13.2.3.2;38.7.2.3.2 Variation 2: Trapping with Carbonyl Compounds;295
1.13.2.3.3;38.7.2.3.3 Variation 3: Trapping with Hydrazine Derivatives or Hydroxylamine;296
1.13.2.4;38.7.2.4 Method 4: Homolysis of the O--O Bond: Radical Production;297
1.14;38.8 Product Class 8: Monocyclic Peroxides;302
1.14.1;38.8.1 Product Subclass 1: Three-Membered Cyclic Peroxides (Dioxiranes);302
1.14.1.1;38.8.1.1 Synthesis of Product Subclass 1;302
1.14.1.1.1;38.8.1.1.1 Method 1: Preparation of Dioxiranes Using Oxone;303
1.14.1.2;38.8.1.2 Applications of Product Subclass 1 in Organic Synthesis;305
1.14.1.2.1;38.8.1.2.1 Method 1: Oxidation of Heteroatoms by Dioxiranes;305
1.14.1.2.1.1;38.8.1.2.1.1 Variation 1: Synthesis of Sulfinic Acids;306
1.14.1.2.1.2;38.8.1.2.1.2 Variation 2: Synthesis of Sulfoxides and Sulfones;306
1.14.1.2.1.3;38.8.1.2.1.3 Variation 3: Synthesis of Sulfoximides;310
1.14.1.2.1.4;38.8.1.2.1.4 Variation 4: Synthesis of N-Oxides and Nitro Compounds;310
1.14.1.2.1.5;38.8.1.2.1.5 Variation 5: Synthesis of Hydroxylamines;314
1.14.1.2.1.6;38.8.1.2.1.6 Variation 6: Synthesis of Nitrones and Nitroxide Radicals;316
1.14.1.2.1.7;38.8.1.2.1.7 Variation 7: Synthesis of Hydroxamic Acids;319
1.14.1.2.1.8;38.8.1.2.1.8 Variation 8: Cleavage of C==N Bonds;320
1.14.1.2.1.9;38.8.1.2.1.9 Variation 9: Cleavage of C==P Bonds;324
1.14.1.2.1.10;38.8.1.2.1.10 Variation 10: Cleavage of C==S Bonds;325
1.14.1.2.2;38.8.1.2.2 Method 2: Oxidation of C==C p-Bonds by Dioxiranes;327
1.14.1.2.2.1;38.8.1.2.2.1 Variation 1: Oxidation of Alkenes;327
1.14.1.2.2.2;38.8.1.2.2.2 Variation 2: Oxidation of Allenes;327
1.14.1.2.2.3;38.8.1.2.2.3 Variation 3: Oxidation of Enolates;330
1.14.1.2.2.4;38.8.1.2.2.4 Variation 4: Oxidation of Arenes;333
1.14.1.2.2.5;38.8.1.2.2.5 Variation 5: Oxidation of Alkynes;337
1.14.1.2.3;38.8.1.2.3 Method 3: Oxidation of X--H s-Bonds by Dioxiranes;337
1.14.1.2.3.1;38.8.1.2.3.1 Variation 1: Oxidation of Si--H s-Bonds;337
1.14.1.2.3.2;38.8.1.2.3.2 Variation 2: Oxidation C--H s-Bonds of Saturated Alkanes;338
1.14.1.2.3.3;38.8.1.2.3.3 Variation 3: Oxidation of Activated C--H s-Bonds;341
1.14.1.2.4;38.8.1.2.4 Method 4: Oxidation of Organometallic Compounds by Dioxiranes;343
1.14.2;38.8.2 Product Subclass 2: Four-Membered Cyclic Peroxides (1,2-Dioxetanes and 1,2-Dioxetanones);350
1.14.2.1;38.8.2.1 Synthesis of Product Subclass 2;351
1.14.2.1.1;38.8.2.1.1 Method 1: Cyclization of Halo Hydroperoxides;351
1.14.2.1.1.1;38.8.2.1.1.1 Variation 1: Cyclization of Epoxy Hydroperoxides;353
1.14.2.1.1.2;38.8.2.1.1.2 Variation 2: Cyclization of Unsaturated Hydroperoxides;353
1.14.2.1.1.3;38.8.2.1.1.3 Variation 3: By Cyclomercuration of Allylic Hydroperoxides;355
1.14.2.1.1.4;38.8.2.1.1.4 Variation 4: 1,2-Dioxetanones from a-Hydroperoxy Acids;355
1.14.2.1.2;38.8.2.1.2 Method 2: Singlet Oxygenation of Alkenes;356
1.14.2.1.2.1;38.8.2.1.2.1 Variation 1: By Sensitized Photooxygenation;357
1.14.2.1.2.2;38.8.2.1.2.2 Variation 2: Using Calcium Peroxide--Hydrogen Peroxide Complex;360
1.14.2.1.2.3;38.8.2.1.2.3 Variation 3: Using Sodium Molybdate/Hydrogen Peroxide;361
1.14.2.1.2.4;38.8.2.1.2.4 Variation 4: Using Triethylsilyl Hydrotrioxide;362
1.14.2.1.3;38.8.2.1.3 Method 3: Triplet Oxygenation of Cyclobutadienes;362
1.14.2.1.4;38.8.2.1.4 Method 4: Photocatalytic Oxygenation;363
1.14.2.1.5;38.8.2.1.5 Method 5: Ozonolysis of Vinylsilanes;364
1.14.2.1.6;38.8.2.1.6 Method 6: Oxygenation Using Phosphite Ozonides;365
1.14.2.1.6.1;38.8.2.1.6.1 Variation 1: 1,2-Dioxetanones from Photooxygenation of Ketenes;367
1.14.2.1.7;38.8.2.1.7 Method 7: Electron-Transfer Oxygenation;367
1.14.3;38.8.3 Product Subclass 3: Five-Membered Cyclic Peroxides with No Further Heteroatoms in the Ring (1,2-Dioxolanes and 1,2-Dioxolan-3-ones);372
1.14.3.1;38.8.3.1 Synthesis of Product Subclass 3;373
1.14.3.1.1;38.8.3.1.1 Method 1: Cyclization of Hydroperoxides;373
1.14.3.1.1.1;38.8.3.1.1.1 Variation 1: Of Bromo Hydroperoxides;373
1.14.3.1.1.2;38.8.3.1.1.2 Variation 2: Of Epoxy Hydroperoxides;374
1.14.3.1.1.3;38.8.3.1.1.3 Variation 3: Of Vinyl Hydroperoxides;374
1.14.3.1.1.4;38.8.3.1.1.4 Variation 4: Of Stannylalkenyl Hydroperoxides;376
1.14.3.1.1.5;38.8.3.1.1.5 Variation 5: Of a-Alkoxy Hydroperoxides;377
1.14.3.1.1.6;38.8.3.1.1.6 Variation 6: Lead(IV) Acetate Mediated Cyclization of 3-Phenylpropyl Hydroperoxides;377
1.14.3.1.2;38.8.3.1.2 Method 2: Cyclization of Haloalkyl Peroxides;378
1.14.3.1.3;38.8.3.1.3 Method 3: Cyclization of Oxetane Hydroperoxyacetals;378
1.14.3.1.4;38.8.3.1.4 Method 4: Oxidation of a,ß-Unsaturated Ketones by Hydrogen Peroxide;380
1.14.3.1.5;38.8.3.1.5 Method 5: Peroxymercuration/Demercuration;382
1.14.3.1.6;38.8.3.1.6 Method 6: Cycloaddition of Carbonyl Oxides to C--C Multiple Bonds;383
1.14.3.1.6.1;38.8.3.1.6.1 Variation 1: From 1,2,4-Trioxolanes;383
1.14.3.1.6.2;38.8.3.1.6.2 Variation 2: Via Peroxycarbenium Ions;385
1.14.3.1.7;38.8.3.1.7 Method 7: Singlet Oxygenation;386
1.14.3.1.7.1;38.8.3.1.7.1 Variation 1: Of 2-Methylacrylic Acids, Leading to 3-Hydroperoxy Acids;386
1.14.3.1.7.2;38.8.3.1.7.2 Variation 2: Of Enones;387
1.14.3.1.7.3;38.8.3.1.7.3 Variation 3: Of Cyclopropanes;388
1.14.3.1.7.4;38.8.3.1.7.4 Variation 4: Of a,ß-Unsaturated Aldimines;389
1.14.3.1.8;38.8.3.1.8 Method 8: Radical-Mediated Oxygenation;389
1.14.3.1.8.1;38.8.3.1.8.1 Variation 1: Addition of Molecular Oxygen to Cyclopropanes;389
1.14.3.1.8.2;38.8.3.1.8.2 Variation 2: From Stable Schlenk Hydrocarbon Diradicals;393
1.14.3.1.8.3;38.8.3.1.8.3 Variation 3: Peroxidation of 1,4-Dienes and Vinylcyclopropanes with Cobalt(II)/Oxygen/Triethylsilane;394
1.14.3.1.8.4;38.8.3.1.8.4 Variation 4: Photolysis or Thermolysis of Alkylidene Azoalkanes;395
1.14.3.1.8.5;38.8.3.1.8.5 Variation 5: Thiol--Alkene Co-oxygenation;396
1.14.3.1.8.6;38.8.3.1.8.6 Variation 6: Halogen-Mediated Peroxidations;397
1.14.3.1.9;38.8.3.1.9 Method 9: ß-Fragmentation of Alkoxy Radicals;397
1.14.3.1.10;38.8.3.1.10 Method 10: Synthesis from Benzo-Fused Bicyclic Sulfonium Salts;399
1.14.3.1.11;38.8.3.1.11 Method 11: Ozonolysis;400
1.14.3.1.12;38.8.3.1.12 Method 12: Peroxide Addition;402
1.14.4;38.8.4 Product Subclass 4: Five-Membered Cyclic Peroxides with One Further Oxygen Atom in the Ring (1,2,4-Trioxolanes);406
1.14.4.1;38.8.4.1 Synthesis of Product Subclass 4;407
1.14.4.1.1;38.8.4.1.1 Method 1: Ozonolysis of Alkenes;407
1.14.4.1.2;38.8.4.1.2 Method 2: Cycloaddition of Carbonyl Oxides to C==O Bonds;412
1.14.4.1.2.1;38.8.4.1.2.1 Variation 1: From the Ozonolysis of Cycloalkadienes in the Presence of Carbonyl Compounds;414
1.14.4.1.2.2;38.8.4.1.2.2 Variation 2: Griesbaum Co-ozonolysis;414
1.14.4.1.3;38.8.4.1.3 Method 3: Ozonolysis of Acetylenic Substrates;416
1.14.4.1.4;38.8.4.1.4 Method 4: Photooxygenation;417
1.14.4.1.4.1;38.8.4.1.4.1 Variation 1: Of Epoxides;417
1.14.4.1.4.2;38.8.4.1.4.2 Variation 2: Of Furans;418
1.14.4.1.4.3;38.8.4.1.4.3 Variation 3: Of Diazo Compounds and Azines;419
1.14.5;38.8.5 Product Subclass 5: Six-Membered Cyclic Peroxides with No Further Heteroatoms in the Ring (1,2-Dioxanes and 3,6-Dihydro-1,2-dioxins);424
1.14.5.1;38.8.5.1 Synthesis of Product Subclass 5;425
1.14.5.1.1;38.8.5.1.1 Method 1: Cyclization of Hydroperoxides;425
1.14.5.1.1.1;38.8.5.1.1.1 Variation 1: Cyclization of Halo Hydroperoxides;425
1.14.5.1.1.2;38.8.5.1.1.2 Variation 2: Cyclization of Epoxy Hydroperoxides;426
1.14.5.1.1.3;38.8.5.1.1.3 Variation 3: Cyclization of Vinyl Hydroperoxides;427
1.14.5.1.1.4;38.8.5.1.1.4 Variation 4: Cyclization of Oxetane Hydroperoxides;428
1.14.5.1.2;38.8.5.1.2 Method 2: Cyclization of Unsaturated Hydroperoxyacetals;429
1.14.5.1.3;38.8.5.1.3 Method 3: Cycloaddition of Carbonyl Oxides to C--C Multiple Bonds;431
1.14.5.1.4;38.8.5.1.4 Method 4: Ozonolysis of Alkylidenecyclopropanes;433
1.14.5.1.5;38.8.5.1.5 Method 5: Singlet Oxygenation of 1,3-Dienes and Related Compounds;434
1.14.5.1.6;38.8.5.1.6 Method 6: Radical-Mediated Oxygenation;436
1.14.5.1.6.1;38.8.5.1.6.1 Variation 1: Thiol--Alkene Co-oxygenation;436
1.14.5.1.6.2;38.8.5.1.6.2 Variation 2: Free-Radical Cyclization of Alkenes with Carbonyl Compounds;436
1.14.5.1.6.3;38.8.5.1.6.3 Variation 3: Peroxyl-Radical Cyclization;438
1.14.5.1.6.4;38.8.5.1.6.4 Variation 4: Peroxidation with Cobalt(II)/Oxygen/Triethylsilane;439
1.14.5.1.6.5;38.8.5.1.6.5 Variation 5: Oxygen Addition to Carbon-Centered Radicals;440
1.14.5.1.6.6;38.8.5.1.6.6 Variation 6: Lead(IV) Acetate Mediated Cyclization of .-Phenyl Hydroperoxides;441
1.14.5.1.6.7;38.8.5.1.6.7 Variation 7: Addition of Molecular Oxygen to Alkenes;441
1.14.5.1.7;38.8.5.1.7 Method 7: Photoenolization and Oxygenation of a,ß-Unsaturated Ketones;442
1.14.5.1.8;38.8.5.1.8 Method 8: Nucleophilic Addition of Peroxides;444
1.14.6;38.8.6 Product Subclass 6: Six-Membered Cyclic Peroxides with One Further Oxygen Atom in the Ring (1,2,4-Trioxanes);448
1.14.6.1;38.8.6.1 Synthesis of Product Subclass 6;449
1.14.6.1.1;38.8.6.1.1 Method 1: Synthesis from Hydroperoxides;449
1.14.6.1.1.1;38.8.6.1.1.1 Variation 1: Condensation of ß-Hydroperoxy Alcohols with Aldehydes or Ketones;449
1.14.6.1.1.2;38.8.6.1.1.2 Variation 2: Cyclization of Unsaturated Hydroperoxyacetals;454
1.14.6.1.1.3;38.8.6.1.1.3 Variation 3: Autoxidation of Unsaturated Hydroperoxyacetals;457
1.14.6.1.1.4;38.8.6.1.1.4 Variation 4: From Epoxy Hydroperoxides;458
1.14.6.1.2;38.8.6.1.2 Method 2: Cyclization of Allylic Peroxyhemiketals;458
1.14.6.1.2.1;38.8.6.1.2.1 Variation 1: Mercury(II)-Mediated Cyclization of Unsaturated Peroxyhemiketals;459
1.14.6.1.3;38.8.6.1.3 Method 3: Cyclization of Silyl Peroxyhemiketals in the Presence of Aldehydes and Ketones;460
1.14.6.1.3.1;38.8.6.1.3.1 Variation 1: 1,2,4-Trioxan-5-ones from a-(Trimethylsilylperoxy) Esters;460
1.14.6.1.4;38.8.6.1.4 Method 4: Photooxygenation;461
1.14.6.1.5;38.8.6.1.5 Method 5: Synthesis from 1,2-Dioxetanes: The Posner Reaction;462
1.14.6.1.6;38.8.6.1.6 Method 6: Miscellaneous Methods Employing Bridged Cyclic Peroxides;466
1.14.6.1.7;38.8.6.1.7 Method 7: Addition of Oxygen to Allylic Hydroperoxides;468
1.14.6.1.8;38.8.6.1.8 Method 8: Trapping of Paterno--Büchi 1,4-Diradicals by Molecular Oxygen;471
1.14.6.1.9;38.8.6.1.9 Method 9: Autoxidation of Imines in the Presence of Aldehydes;472
1.14.7;38.8.7 Product Subclass 7: Six-Membered Cyclic Peroxides with Two Further Oxygen Atoms in the Ring (1,2,4,5-Tetroxanes);476
1.14.7.1;38.8.7.1 Synthesis of Product Subclass 7;477
1.14.7.1.1;38.8.7.1.1 Method 1: Synthesis from Aldehydes or Ketones;477
1.14.7.1.1.1;38.8.7.1.1.1 Variation 1: Reaction of Aldehydes or Ketones with Bis(trimethylsilyl) Peroxide;483
1.14.7.1.2;38.8.7.1.2 Method 2: Synthesis by Ozonolysis;485
1.14.7.1.2.1;38.8.7.1.2.1 Variation 1: Of O-Methyloximes;488
1.14.7.1.3;38.8.7.1.3 Method 3: Synthesis from 1,2,4-Trioxolanes;489
1.14.7.1.4;38.8.7.1.4 Methods 4: Miscellaneous Methods;490
1.15;38.9 Product Class 9: Larger-Ring Cyclic Peroxides and Endoperoxides;496
1.15.1;38.9.1 Synthesis of Product Class 9;496
1.15.1.1;38.9.1.1 Method 1: Peroxidation with Triplet Molecular Oxygen;496
1.15.1.1.1;38.9.1.1.1 Variation 1: Cycloaddition of Triplet Dioxygen to Biradicals;496
1.15.1.1.2;38.9.1.1.2 Variation 2: Cycloaddition of Triplet Oxygen to an o-Quinodimethane System;497
1.15.1.1.3;38.9.1.1.3 Variation 3: Electron-Transfer-Induced Photooxidation of 1,6-Dienes with Triplet Oxygen;498
1.15.1.1.4;38.9.1.1.4 Variation 4: Lewis Acid Induced Peroxidation of 1,3-Dienes;500
1.15.1.1.5;38.9.1.1.5 Variation 5: Autoxidation of Nonconjugated 1,4-Dienes;501
1.15.1.1.6;38.9.1.1.6 Variation 6: Thiol--Alkene Co-oxygenation;502
1.15.1.1.7;38.9.1.1.7 Variation 7: Cobalt(II)-Catalyzed Peroxidation of 1,5-Dienes with Molecular Oxygen and Triethylsilane;505
1.15.1.2;38.9.1.2 Method 2: Oxidation of Cyclic Unsaturated Compounds with Photochemically Generated Singlet Oxygen;506
1.15.1.2.1;38.9.1.2.1 Variation 1: Photooxidation of Naphthalene Derivatives;507
1.15.1.2.2;38.9.1.2.2 Variation 2: Photooxidation of Anthracene and Pentacene Derivatives;510
1.15.1.2.3;38.9.1.2.3 Variation 3: Photooxidation of Strained Metacyclophanes;512
1.15.1.2.4;38.9.1.2.4 Variation 4: Photooxidation of Cyclopentadiene and Cyclohexa-1,3- or Cyclohexa-1,4-diene Systems;512
1.15.1.2.5;38.9.1.2.5 Variation 5: Photooxidation of Cycloheptadiene/triene Systems;515
1.15.1.2.6;38.9.1.2.6 Variation 6: Photooxidation of Cyclooctadiene/triene/tetraene Systems;519
1.15.1.3;38.9.1.3 Method 3: Oxidation of Cyclic Unsaturated Compounds by Chemically Generated Singlet Oxygen;520
1.15.1.4;38.9.1.4 Method 4: Cyclization of Hydroperoxides and Their Derivatives through Nucleophilic Substitution;521
1.15.1.4.1;38.9.1.4.1 Variation 1: Cyclization of Bromo Hydroperoxides;521
1.15.1.4.2;38.9.1.4.2 Variation 2: Acid-Catalyzed Cyclization of Epoxy Hydroperoxides;523
1.15.1.4.3;38.9.1.4.3 Variation 3: Trimethylsilyl Trifluoromethanesulfonate Catalyzed Intramolecular Cyclization of Silyl Peroxides;523
1.15.1.4.4;38.9.1.4.4 Variation 4: Peroxide Transfer from Bis(tributyltin) Peroxide;524
1.15.1.4.5;38.9.1.4.5 Variation 5: Cesium Hydroxide or Silver(I) Oxide Mediated Cycloalkylation of Alkane-1,1-diyl Dihydroperoxides and Dihaloalkanes;525
1.15.1.4.6;38.9.1.4.6 Variation 6: Base-Catalyzed Cyclization of Dihydroperoxides and Dialkyldichlorosilanes;526
1.15.1.5;38.9.1.5 Method 5: Cyclization of Unsaturated Hydroperoxides through Intramolecular Nucleophilic Addition;527
1.15.1.5.1;38.9.1.5.1 Variation 1: Halonium Ion Mediated Cyclization of Unsaturated Hydroperoxides;527
1.15.1.5.2;38.9.1.5.2 Variation 2: Base-Catalyzed Intramolecular Cyclization of Unsaturated Hydroperoxides;531
1.15.1.5.3;38.9.1.5.3 Variation 3: Ozonolysis of Unsaturated Hydroperoxides;532
1.15.1.5.4;38.9.1.5.4 Variation 4: Ozonolysis of Vinylsilanes;535
1.15.1.5.5;38.9.1.5.5 Variation 5: Peroxymercuration/Demercuration of Cyclic Dienes;536
1.15.1.5.6;38.9.1.5.6 Variation 6: Intramolecular Capture of ß-Hydroperoxy Cations;537
1.15.1.6;38.9.1.6 Method 6: Cycloaddition of Peroxides with Carbonyl Compounds;538
1.15.1.6.1;38.9.1.6.1 Variation 1: Trimethylsilylation of Dihydroperoxides Followed by Trimethylsilyl Trifluoromethanesulfonate Catalyzed Cyclocondensation with Carbonyl Compounds;538
1.15.1.6.2;38.9.1.6.2 Variation 2: Acid-Catalyzed Condensation of .- or d-Hydroxy Hydroperoxides and Ketones;539
1.15.1.6.3;38.9.1.6.3 Variation 3: Acid-Catalyzed Condensation of 3-Methyl-3-(triethylsilylperoxy)butan-1-ol and Carbonyl Compounds;541
1.15.1.7;38.9.1.7 Method 7: Synthesis with Retention of the Functional Group;542
1.15.1.7.1;38.9.1.7.1 Variation 1: Reduction of C==C Bonds in Unsaturated Bicyclic Peroxides;542
1.15.1.7.2;38.9.1.7.2 Variation 2: Chlorination of Unsaturated Bicyclic Peroxides;544
1.15.1.7.3;38.9.1.7.3 Variation 3: Selective Reduction of the Hydroperoxide Group in Hydroperoxy Endoperoxides;544
1.15.1.7.4;38.9.1.7.4 Variation 4: Dehydration of Hydroperoxy-Substituted Endoperoxides;544
1.15.1.7.5;38.9.1.7.5 Variation 5: Reduction of a Ketone Group in Endoperoxides;546
1.15.1.7.6;38.9.1.7.6 Variation 6: Oxidation of Hydroxy Endoperoxides;546
1.15.1.7.7;38.9.1.7.7 Variation 7: Diels--Alder Reaction with Dimethyl 1,2,4,5-Tetrazine-3,6-dicarboxylate;547
1.15.1.7.8;38.9.1.7.8 Variation 8: Reductive Debromination with Tributyltin Hydride;547
1.15.1.7.9;38.9.1.7.9 Variation 9: Silver(I) Oxide Mediated Methylation of Hydroperoxy-Substituted Endoperoxides;548
1.16;Keyword Index;552
1.17;Author Index;582
1.18;Abbreviations;604mehr

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