3 Review(s)

The development of more effective routes to known materials and the production of new materials are important goals in many areas, including electronics, agriculture, medicine and textiles. Organic synthesis is central to achieving these goals. Comprehensive Organic Synthesisdraws together the common themes that underlie the many apparently disparate areas of organic chemistry which underpin synthetic strategies, thus providing a comprehensive overview of this important discipline. The contributions have been organized to reflect the way in which synthetic chemists approach a problem. In terms of organic molecules, the work is divided into formation of carbon-carbon bonds, introduction of heteroatoms and heteroatom interconversions. Thus, Volumes 1-5 focus on carbon-carbon formation, but also include aspects of heteroatom introduction. Volumes 6-8 concentrate on interconversion of heteroatoms, but also deal with exchange of carbon-carbon bonds for carbon-heteroatom bonds. Organization of the chapters is along the theme of selectivity, which is a critical question in determining the suitability of a synthetic method. Volume 9 contains cumulative author and subject indexes. Comprehensive Organic Synthesis will appeal to a wide audience. The set will be an essential reference work for all those seeking information on the solution of synthetic problems, whether they be experienced practitioners or chemists whose major interests lie outside organic synthesis. In addition, synthetic chemists requiring the essential facts in new areas, as well as students completely new to the field, will find Comprehensive Organic Synthesis an invaluable source, providing authoritative accounts of the essential facts and concepts. Subjects of the book : Chemistry Contents of the book : Preface Contributors to Volume 1 Abbreviations Contents of All Volumes Nonstabilized Carbanion Equivalents 1.1 Carbanions of Alkali and Alkaline Earth Cations: (i) Synthesis and Structural Characterization 1.2 Carbanions of Alkali And Alkaline Earth Cations: (ii) Selectivity of Carbonyl Addition Reactions 1.3 Organoaluminum Reagents 1.4 Organocopper Reagents 1.5 Organotitanium and Organozirconium Reagents 1.6 Organochromium Reagents 1.7 Organozinc, Organocadmium and Organomercury Reagents 1.8 Organocerium Reagents 1.9 Samarium and Ytterbium Reagents 1.10 Lewis Acid Carbonyl Complexation 1.11 Lewis Acid Promoted Addition Reactions of Organometallic Compounds 1.12 Nucleophilic Addition to Imines and Imine Derivatives 1.13 Nucleophilic Addition to Carboxylic Acid Derivatives Heteroatom-stabilized Carbanion Equivalents 2.1 Nitrogen Stabilization 2.2 Boron Stabilization 2.3 Sulfur Stabilization 2.4 The Benzoin and Related Acyl Anion Equivalent Reactions 2.5 Silicon Stabilization 2.6 Selenium Stabilization Transformation of the Corbonyl Group into Nonhydroxylic Groups 3.1 Alkene Synthesis 3.2 Epoxidation and Related Processes 3.3 Skeletal Reorganizations: Chain Extension and Ring Expansion Author Index Subject Index Volume 2 Uncatalyzed Additions of Nucleophilic Alkenes to C=X 1.1 Allyl Organometallics 1.2 Heteroatom-stabilized Allylic Anions 1.3 Propargyl and Allenyl Organometallics 1.4 Formation of Enolates 1.5 The Aldol Reaction: Acid and General Base Catalysis 1.6 The Aldol Reaction: Group I and Group II Enolates 1.7 The Aldol Reaction: Group III Enolates 1.8 Zinc Enolates: the Reformatsky and Blaise Reactions 1.9 The Aldol Reaction: Transition Metal Enolates 1.10 The Henry (Nitroaldol) Reaction 1.11 The Knoevenagel Reaction 1.12 Darzens Glycidic Ester Condensation 1.14 Metal Homoenolates 1.15 Use of Enzymatic Aldol Reactions in Synthesis 1.16 Metalloenamines 1.17 Hydrazone Anions Catalyzed Additions of Nucleophilic Alkenes to C=X 2.1 The Prins and Carbonyl Ene Reactions 2.2 Allylsilanes, Allylstannanes and Related Systems 2.3 Formation and Addition Reactions of Enol Ethers 2.4 Asymmetric Synthesis with Enol Ethers 2.5 Reactions of Activated Dienes with Aldehydes Addition-Elimination Reactions (Acylations) 3.1 The Aliphatic Friedel-Crafts Reaction 3.2 The Bimolecular Aromatic Friedel-Crafts Reaction 3.3 The Intramolecular Aromatic Fridel-Crafts Reaction 3.4 The Reimer-Tiemann Reaction 3.5 The Vilsmeier-Haack Reaction 3.6 Acylation of Esters, Ketones and Nitriles 3.7 The Eschenmoser Coupling Reaction Additions of Nucleophilic Alkenes to C=NR and C=NR2+ 4.1 The Bimolecular Aliphatic Mannich and Related Reactions 4.2 The Bimolecular Aromatic Mannich Reaction 4.3 Reactions of Allyl and Propargyl/Allenic Organometallics with Imines and Iminium Ions 4.4 The Intramolecular mannich and related Reactions 4.5 Additions to N-Acyliminium Ions 4.6 The Passerini and Ugi Reactions Author Index Subject Index Volume 3 Alkylation of Carbon 1.1 Alkylations of Enols and Enolates 1.2 Alkylations of Nitrogen-stabilized Carbanions 1.3 Alkylations of Sulfur- and Selenium-containing Carbanions 1.4 Alkylations of Other Heteroatom-stabilized Carbanions 1.5 Alkylations of Nonstabilized Carbanions 1.6 Alkylations of Vinyl Carbanions 1.7 Alkylationa of Alkynyl Carbanions 1.8 Friedel-Crafts Alkylations 1.9 Transannular Electrophilic Cyclizations Coupling Reactions 2.1 Coupling Reactions Between sp3 Carbon Centers 2.2 Coupling Reactions Between sp3 and sp2 Carbon Centers 2.3 Coupling Reactions Between sp2 Carbon Centers 2.4 Coupling Reactions Between sp2 and sp Carbon Centers 2.5 Coupling Reactions Between sp Carbon Centers 2.6 Pinacol Coupling Reactions 2.7 Acyloin Coupling Reactions 2.8 Kolbe Reactions 2.9 Oxidative Coupling of Phenols and Phenol Ethers Rearrangement Reactions 3.1 Wagner-Meerwein Rearrangements 3.2 The Pinacol Rearrangement 3.3 Acid-catalyzed Rearrangements of Epoxides 3.4 The Semipinacol and other Rearrangements 3.5 Dienone-Phenol Rearrangements and Related Reactions 3.6 Benzil-Benzilic Acid Rearrangements 3.7 The Favorskii Rearrangement 3.8 The Ramberg-Backlund Rearrangement 3.9 The Wolff Rearrangement 3.10 The Stevens and Related Rearrangements 3.11 The Wittig Rearrangement Other Carbon-Carbon Bond Forming Reactions 4.1 Carbonylation and Decarbonylation Reactions 4.2 Carbon-Carbon Bond Formation by C-H insertion Author Index Subjet Index Volume 4 Polar Additions to Activated Alkenes and Alkynes 1.1 Stabilized Nucleophiles with Electron Deficient Alkenes and Alkynes 1.2 Sonjugate Additions of Reactive Carbanions to Activated Alkenes and Alkynes 1.3 Conjugate Additions of Carbon Ligands to Activated Alkenes and Alkynes Mediated by Lewis Acids 1.4 Organocuprates in the Conjugate Addition Reaction 1.5 Asymmetric Nucleophilic Additions to Electron Deficient Alkenes 1.6 Nucleophilic Addition-Electrophilic Coupling with a Carbanion Intermediate 1.7 Addition of H-X Reagents to Alkenes and Alkynes 1.8 Electrophilic Addition of X_Y Reagents to Alkenes and Alkynes 1.9 Electrophilic Heteroatom Cyclizations Nucleophilic Aromatic Substitutions 2.1 Arene Substitution via Nucleophilic Addition to Electron Deficient Arenes 2.2 Nucleophilic Coupling with Aryl Radicals 2.3 Nucleophilic Coupling with Arynes 2.4 Nucleophili Addition to Arene-Metal Complexes Polar Additions to Alkenes and Slkynes 3.1 Heteroatom Nucleophiles with Metal-activated alkenes and Alkynes 3.2 Carbon Nucleophiles with Alkenes and Alkynes 3.3 Nucleophiles with Allyl-Metal Complexes 3.4 Nucleophies with Cationic Pentadienyl-Metal Complexes 3.5 Carbon Electrophiles with Dienes and Polyenes Pormoted by Transition Metals Nonpolar Additions to Alkenes and Alkynes 4.1 Radical Addition Reactions 4.2 Radical Cyclizations and Sequential Radical Reactions 4.3 Vinyl Subtitutions with Organopalladium Intermediates 4.4 Carboetallation of Alkenes and Alkynes 4.5 Hydroformylation and Related Additions of Carbon Monoxide to Alkenes and Alkynes 4.6 Methylene and Nunfunctionalized alkylidene Transfer to Form Cyclopropanes 4.7 Formation and Further Transformations of 1,1-Dihalocyclopropanes 4.8 Addition of Ketocarbenes to Alkenes, Alkynes and Aromatic Systems 4.9 Intermolecular 1,3-Dipolar Cycloadditions 4.10 Intramolecular 1,3-Dipolar Cycloadditions Author Index Subject Index Volume 5 Ene Reactions 1.1 Ene Reactions with Alkenes as Enophiles 1.2 Metallo-ene Reactions [2 + 2] Cycloadditions 2.1 Thermal Cyclobutane Ring Formation 2.2 Formation of Four-membered Heterocycles 2.3 Photochemical Cycloadditions 2.4 The Paterno-Buchi Reaction 2.5 Di-?-methane Photoisomerizations 2.6 Oxa-di-?-methane Photoisomerizations [3 +2] Cycloadditions 3.1 Thermal Cycloadditons 3.2 Transition Metal Mediated Cycloadditions [4 + 2] Cycloadditions 4.1 Intermolecular Diels-Alder Reactions 4.2 Heterodienophile Additions to Dienes 4.3 Heterodiene Additions 4.4 Intramolecular Diels-Alder Reactions 4.5 Retrograde Diels-Alder Reactions Higher-order Processes 5.1 [4 + 3] Cycloadditions 5.2 [4 + 4] and [6 + 4] Cycloadditions 5.3 [3 + 2] and [5 + 2] Arene-Alkene Photocycloadditions Electrocyclic Processes 6.1 Cyclobutene Ring Opening Reactions 6.2 1,3-Cyclohexadiene Formation Reactions 6.3 Nazarov and Related Cationic Cyclizations Sigmatropic Processes 7.1 Cope, Oxy-Cope and Anionic Oxy-Cope Rearrangements 7.2 Claisen Rearrangements 7.3 Consecutive Rearrangements Small Ring Rearrangements 8.1 Rearrangements of Vinylcyclopropanes and Related Systems 8.2 Rearrangements of Divinylcyclopropanes 8.3 Charge-accelerated Rearrangements Other Transition Metal Associated Reactions 9.1 The Pauson-Khand Reaction 9.2 Metal-Carbene Cycloadditions 9.3 Alkene Metathesis and Related Reactions 9.4 [2 + 2 + 2] Cycloadditions 9.5 Zirconium-promoted Bicyclization of Enynes 9.6 Metal-catalyzed Cycloadditions of Small Ring Compounds Author Index Subject Index Volume 6 Displacement by substitution Processes 1.1 Synthesis of Alcohols and Ethers 1.2 Synthesis of Glycosides 1.3 Synthesis of Amines and Ammonium Salts 1.4 Synthesis of Nitroso, Nitro and Related Compounds 1.5 Synthesis of Sulfides, Sulfoxides and Sulfones 1.6 Synthesis of Phosphonium Ylides 1.7 Synthesis of Halides 1.8 synthesis of Pseudohalides, Nitriles and Related Compounds 1.9 Ritter-type Reactions Acylation-type Reactions 2.1 Synthesis of Acid Halides, Anhydrides and Related Compounds 2.2 Synthesis of Esters, Activated Esters and Lactones 2.3 Synthesis of Amides and Related Compounds 2.4 Synthesis of Thioamides and Thiolactams 2.5 Synthesis of Thioesters and Thiolactones 2.6 Selenoesters of All Oxidation States 2.7 Synthesis of Iminium Salts, Orthoesters And Related Compounds 2.8 Inorganic Acid Derivatives Protecting Groups 3.1 Protecting Groups Functional Group interconversion 4.1 Carbonyl Group Derivatization 4.2 Use of Carbonyl Derivatives for Heterocyclic Synthesis 4.3 Functional Group Transformations via Carbonyl Derivatives 4.4 Degradation Reactions 4.5 Functional Group Transformations via Allyl Rearrangement 4.6 2,3-Sigmatropic Rearrangements 4.7 Polonovski- and Pummerer-type Reactions and the Nef Reaction Elimination Reactions 5.1 Eliminations to Form Alkenes, Allenes and Alkynes and Related Reactions 5.2 Reductive Elimination, Vicinal Deoxygenation and Vicinal Desilylation 5.3 The Cope Elimination, Sulfoxide Elimination and Related Thermal Reactions 5.4 Fragmentation Reactions Author Index Subject Index Volume 7 Oxidation of Unactivated C-H Bonds 1.1 Oxidation by Chemical Methods 1.2 Oxidation by Nitrene Insertion 1.3 Oxidation by Remote Functionalization Methods 1.4 Oxidation by Microbial Methods Oxidation of Activated C-H Bonds 2.1 Oxidation Adjacent to C=C Bonds 2.2 Oxidation Adjacent to C=X Bonds by Dehydrogenation 2.3 Oxidation Adjacent to C=X Bonds by Hydroxylation Methods 2.4 Oxidation Adjacent to Sulfur 2.5 Oxidation Adjacent to Nitrogen 2.6 Oxidation Adjacent to Oxygen of Ethers 2.7 Oxidation Adjacent to Oxygen of Alcohols by Chromium Reagents 2.8 Oxidation Adjacent to Oxygen of Alcohols by Activated DMSO Methods 2.9 Oxidation Adjacent to Oxygen of Alcohols by Other Methods 2.10 Vinylic and Arylic C-H Oxidation 2.11 Synthesis of Quinones Oxidation of C=C Bonds 3.1 Addition Reactions with Formation of Carbon-Oxygen Bonds: (i) General Methods of Epoxidation 3.2 Addition Reactions with Formation of Carbon-Oxygen Bonds: (ii) Asymmetric Methods of Epoxidation 3.3 Addition Reactions with Formation of Carbon-Oxygen Bonds: (iii) Glycol Forming Reactions 3.4 Addition Reactions with Formation of Carbon-Oxygen Bonds: (iv) The Wacker Oxidation and Related Reactions 3.5 Addition Reactions with Formation of Carbon-Nitrogen Bonds 3.6 Addition Reactions with Formation of Carbon-Sulfur or Carbon-Selenium Bonds 3.7 Addition Reactions with Formation of Carbon-Halogen Bonds 3.8 Cleavage Reactions Oxidation of C-X Bonds 4.1 Oxidation of Carbon-Boron Bonds 4.2 Oxidation of Carbon-Metal Bonds 4.3 Oxidation of Carbon-Silicon Bonds 4.4 Oxidation of Carbon-Halogen Bonds Oxidation Of C-C Bonds 5.1 The Baeyer- Villiger Reaction 5.2 The Beckmann and Related Reactions 5.3 Glycol Cleavage Reactions 5.4 The Hunsdiecker and Related Reactions Oxidation of Heteroatoms 6.1 Oxidation of Nitrogen and Phosphorus 6.2 Oxidation of Sulfur, Selenium and Tellurium Special Topics 7.1 Oxidation by Electrochemical Mehtods 7.2 Oxidative Rearrangement Reactions 7.3 Solid-supported Oxidants 7.4 Electron-transfer Oxidation Author Index Subject Index Volume 8 Reduction of C=X Bonds 1.1 Reduction of C=O to CHOH by Metal Hydrides 1.2 Reduction of C=N to CHNH by Metal Hydrides 1.3 Reduction of C=X to CHXH by Hydride Delivery from Carbon 1.4 Reduction of C=X to CHXH by Dissolving Metals and Related Methods 1.5 Reduction of C=X to CHXH Electrolytically 1.6 Reduction of C=X to CHXH by Catalytic Hydrogenation 1.7 Reduction of C=X to CHXH by Chirally Modified Hydride Reagents 1.8 Reduction of C=X to CHXH Using Enzymes and Microorganisms 1.9 Reduction of Acetals, Azaacetals and Thioacetals to Ethers 1.10 Reduction of Carboxylic Acid Derivatives to Alcohols, Ethers and Amines 1.11 Reduction of Carboxylic Acids to Aldehydes by Metal Hydrides 1.12 Reduction of Carboxylic Acids to Aldehydes by Other Methods 1.13 Reduction of C=X to CH2 by Dissolving Metals and Related Methods 1.14 Reduction of C=X to CH2 by Wolff-Kishner and Other Hydrazone Methods Reduction Of X=Y Bonds 2.1 Reduction of Nitro and Nirtroso Compounds 2.2 Reduction of N=N, N-N, N-O and O-O Bonds 2.3 Reduction of S=O and SO2 to S, P=O to P, and of S-X to S-H Reduction of C=C and C=C Bonds 3.1 Heterogeneous Catalytic Hydrogenation of C=C and C=C 3.2 Homogeneous Catalytic Hydrogenation of C=C and C=C 3.3 Reduction of C=C and C=C by Noncatalytic Chemical Methods 3.4 Partial Reduction of Aromatic Rings by Dissolving Metals and Other Methods 3.5 partial reduction of Enones, Styrenes and Related Systems 3.6 Partial and Complete Reduction of Pyridines and their Benzo Analogs 3.7 Partial and Complete Reduction of Pyrroles, Furans, Thiophenes and Their Benzo Analogs 3.8 Partial and Complete Reduction of Heterocycles Containing More than One Heteroatom 3.9 hydrozirconation of C=C and C=C, and Hydrometallation by Other Metals 3.10 Hydroboration of C=C and C=C 3.11 Hydroalumination of C=C and C=C 3.12 Hydrosilylation of C=C and C=C Reduction of C-X to C-H 4.1 Reduction of Saturated Alkyl Halides to Alkanes 4.2 Reduction og Saturated Alcohols and Amines to Alkanes 4.3 Reduction of Heteroatoms Bonded to Tetrahedral Carbon 4.4 Reduction of Epoxides 4.5 Reduction of Vinyl Halides to Alkenes, and of Aryl Halides to Arenes 4.6 Reduction of Ketones to Alkenes 4.7 Hydrogenolysis of Allyl and Benzyl Halides and Related Compounds 4.8 Reduction of ?-Substituted Carbonyl Compounds-CX-CO- to Carbonyl Compounds-CH-CO- Author Index Subject Index Voulme 9 Cumulative Author Index Cumulative Subject Index