Selected chapters: Uncatalyzed Additions of Nucleophilic Alkenes to C=X |
Allyl organometallics |
Heteroatom-stabilized allylic anions |
Propargyl and allenyl organometallics |
The Aldol reaction: general acid and base catalysis |
The Aldol reaction: group I and group II enolates |
The Aldol reaction: group III enolates |
Zinc enolates: the Reformatsky and Blaise Reactions |
The Aldol reaction: transition metal enolates |
The Knoevenagel reaction |
The Perkin reaction |
Darzens' glycidic ester condensation |
Use of enzymatic Aldol reactions in synthesis |
Metalloenamines |
Hydrazone anions |
Catalyzed Additions of Nucleophilic Alkenes to C=X |
The Prins and related reactions |
Allylsilanes, allylstannanes and related systems |
Asymmetric synthesis with enol ethers |
Reactions of activated dienes with aldehydes |
Addition-Elimination Reactions (Acylations) |
The aliphatic Friedel-Crafts reaction |
The biomolecular aromatic Friedel-Crafts reaction |
The Reimer-Tiemann reaction |
The Vilsmeier-Haack reaction |
Acylation of esters, ketones and nitriles |
The Eschenmoser coupling reaction |
Additions of Nucleophilic Alkenes to C=NR and C=NR 2 + |
The bimolecular aliphatic Mannich and related reactions |
The bimolecular aromatic Mannich reaction |
The intramolecular Mannich and related reactions |
Additions to Nlt;/i>-acyliminium ions |
The Passerini and Ugi reactions |
Author index |
Subject index |
Polar Additions to Activated Alkenes and Alkynes |
Stabilized nucleophiles with electron deficient alkenes and alkynes |
Conjugate additions of reactive carbanions to activated alkenes and alkynes |
Conjugate additions of carbon ligands to activated alkenes and alkynes mediated by Lewis acids |
Organocuprates in the conjugate addition reaction |
Asymmetric nucleophilic addition to electron deficient alkenes |
Nucleophilic addition-electrophilic coupling with a carbanion intermediate |
Addition of H-X reagents to alkenes and alkynes |
Electrophilic addition of X-Y reagents to alkenes and alkynes |
Electrophilic heteroatom cyclizations |
Nucleophilic Aromatic Substitutions |
Arene substitution via nucleophilic addition to electron deficient arenes |
Nucleophilic coupling with aryl radicals |
Nucleophilic coupling with arynes |
Nucleophilic addition to arene-metal complexes |
Polar Additions to Alkenes and Alkynes |
Heteroatom nucleophiles with metal-activated alkenes and alkynes |
Carbon nucleophiles with alkenes and alkynes |
Nucleophiles with allyl-metal complexes |
Nucleophiles with cationic pentadienyl-metal complexes |
Carbon electrophiles with dienes and polyenes promoted by transition metals |
Nonpolar Additions to Alkenes and Alkynes |
Radical addition reactions |
Radical cyclizations and sequential radical reactions |
Vinyl substitutions with organopalladium intermediates |
Carbometallation of alkenes and alkynes |
Hydroformylation and related additions of carbon monoxide to alkenes and alkynes |
Methylene and nonfunctionalized alkylidene transfer to form cyclopropanes |
Formation and further transformations of 1,1-dihalocyclopropanes |
Addition of ketocarbenes to alkenes, alkynes and aromatic systems |
Intermolecular 1,3-dipolar cycloadditions |
Intramolecular 1,3-dipolar cycloadditions |
Selected contents: Ene Reactions |
Ene reactions with alkenes as enophiles |
Metallo-ene reactions |
[2 + 2] Cycloadditions |
Thermal cyclobutane ring formation |
Formation of four-membered heterocycles |
Di-pgr;-methane photoisomerizations |
Oxa-di-pgr;-methane photoisomerizations |
[3 + 2] Cycloadditions |
Thermal cycloadditions |
Transition metal mediated cycloadditions |
[4 + 2] Cycloadditions |
Intermolecular Diels-Alder reactions |
Retrograde Diels-Alder reactions |
Higher-Order Cycloadditions |
[4 + 3] cycloadditions |
[4 + 4] and [6 + 4] cycloadditions |
[3 + 2] and [5 + 2] arene-alkene photocyloadditions |
Electrocyclic Processes |
Cyclobutene ring opening reactions |
1,3-cyclohexadiene formation reactions |
Nazarov and related cationic cyclizations |
Sigmatropic Processes |
Cope, oxy-cope and anionic oxy-cope rearrangements |
Claisen rearrangements |
Consecutive rearrangements |
Small-Ring Rearrangements |
Rearrangements of vinylcyclopropanes and related systems |
Charge-accelerated rearrangements |
Other Transition Metal Associated Reactions |
The Pauson-Khand reaction |
Metal-carbene cycloadditions |
Metal-catalyzed cycloaddition of small ring compounds |
Selected contents1 |
Additions to C-X pgr;-Bonds, |
Nonstabilized carbanion equivalents / Part 1: |
Heteroatom-stabilized carbanion equivalents |
Transformation of the carbonyl group into nonhydroxylic groups |
Uncatalyzed additions of nucleophilic alkenes to C=X / 2: |
Catalyzed additions of nulceophilic alkenes to C=X |
Addition-elimination reactions (acylations) |
Additions of nucleophilic alkenes to C=NR and C=NR 2 + |
Carbon-Carbon sgr;-Bond Formation / 3: |
Alkylation of carbon |
Coupling reactions |
Rearrangement reactions |
Other carbon-carbon bond forming reactions |
Additions to and Substitutions at C-C pgr;-Bonds / 4: |
Polar additions to activated alkenes and alkynes |
Nucleophilic aromatic substitutions |
Polar additions to alkenes and alkynes |
Nonpolar additions to alkenes and alkynes |
Combining C-C pgr;-Bonds / 5: |
Ene reactions |
[2+2] cycloadditions |
[3+2] cycloadditions |
[4+2] cycloadditions |
Higher-order cycloadditions |
Electrocyclic processes |
Sigmatropic processes |
Small-ring rearrangements |
Other transition metal associated reactions |
Heteroatom Manipulation / 6: |
Displacement by substitution processes |
Acylation-type reactions |
Protecting groups |
Functional group interconversion |
Elimination reactions |
Oxidation / 7: |
Oxidation of unactivated C-H bonds |
Oxidation of activated C-H bonds |
Oxidation of C=C bonds |
Oxidation of C-X bonds |
Oxidation of C-C bonds |
Oxidation of heteroatoms |
Special topics |
Reduction / 8: |
Reduction of C=X bonds |
Reduction of X=Y bonds |
Reduction of C=C and Cequiv;C bonds |
Reduction of C-X to C-H |
Indexes / 9: |
Cumulative author index |
Cumulative subject index |
Displacement by Substitution Processes |
Synthesis of alcohols and ethers |
Synthesis of glycosides |
Synthesis of amines and ammonium salts |
Synthesis of nitroso, nitro and related compounds |
Synthesis of sulfides, sulfoxides and sulfones |
Synthesis of phosphonium ylides |
Synthesis of halides |
Formation of pseudohalides, nitriles and related compounds |
Ritter-type reactions |
Acylation-Type Reactions |
Synthesis of acid halides, anhydrides and related compounds |
Synthesis of activated esters and related compounds |
Synthesis of amides and related compounds |
Synthesis of thioamides and thiolactams |
Synthesis of thioesters and thiolactones |
Selenoesters of all oxidation states |
Synthesis of iminium salts, orthoesters and related compounds |
Inorganic acid derivatives |
Protecting Groups |
Alcohols, amines and thiols, including multiple protecting groups |
Functional Group Interconversion |
Carbonyl group derivatization |
Use of carbonyl derivatives for heterocyclic synthesis |
Functional group transformations via carbonyl derivatives |
Degradation reactions |
Functional group transformation via allyl rearrangement |
2,3-sigmatropic rearrangements |
Polonovski- and Pummerer-type reactions and the Nef reaction |
Elimination Reactions |
Eliminations to form alkenes, allenes and alkynes and related reactions |
Reductive elimination, vicinal deoxygenation and vicinal desilylation |
The Cope elimination, sulfoxide elimination and related thermal reactions |
Fragmentation reactions |
Selected contents: Oxidation of Unactivated C-H Bonds |
Oxidation by chemical methods |
Oxidation by nitrene insertion |
Oxidation by microbial methods |
Oxidation of Activated C-H Bonds |
Oxidation adjacent to C=C bonds |
Oxidation adjacent to sulfur |
Oxidation adjacent to nitrogen |
Oxidation adjacent to oxygen of ethers |
Oxidation adjacent to oxygen of alcohols by other methods |
Synthesis of quinones |
Oxidation of C=C Bonds |
Addition reactions with formation of carbon-oxygen bonds: (i) General methods of epoxidation |
Addition reactions with formation of carbon-oxygen bonds: (iv) The Wacker oxidation and related reactions |
Addition reactions with formation of carbon-nitrogen bonds |
Cleavage reactions |
Oxidation of C-X Bonds |
Oxidation of carbon-boron bonds |
Oxidation of carbon-metal bonds |
Oxidation of carbon-halogen bonds |
Oxidation of C-C Bonds |
The Baeyer-Villiger reaction |
The Beckmann and related reactions |
Glycol cleavage reactions |
Oxidation of Heteroatoms |
Oxidation of nitrogen and phosphorus |
Oxidation of sulfur, selenium and tellurium |
Special Topics |
Oxidation by electrochemical methods |
Oxidative rearrangement reactions |
Electron transfer oxidation |
Selected contents: Reduction of C=X Bonds |
Reduction of C=O to CHOH by metal hydrides |
Reduction of C=N to CHNH by metal hydrides |
Reduction of C=X to CHXH by hydride delivery from carbon |
Reduction of C=X to CHXH by dissolving metals and related methods |
Reduction of C=X to CHXH by catalytic hydrogenation |
Reduction of carboxylic acids to alcohols, ethers and amines |
Reduction of carboxylic acids to aldehydes by metal hydrides |
Reduction of carboxylic acids to aldehydes by other methods |
Reduction of C=X to CH 2 by dissolving metals and related methods |
Reduction of X=Y Bonds |
Reduction of nitro and nitroso compounds |
Reduction of N=N, N-N, N-O and O-O bonds |
Reduction of S=O and SO 2 to S, of P=O to P, and of S-X to SH |
Reduction of C=C and Cequiv;C Bonds |
Heterogeneous catalytic hydrogenation of C=C and Cequiv;C |
Homogeneous catalytic hydrogenation of C=C and Cequiv;C |
Reduction of C=C and Cequiv;C by noncatalytic chemical methods |
Partial and complete reduction of pyridines and their benzo analogs |
Hydrozirconation of C=C and Cequiv;C, and hydrometallation by other metals |
Hydroboration of C=C and Cequiv;C |
Hydroalumination of C=C and Cequiv;C |
Hydrosilylation of C=C and Cequiv;C |
Reductions of C-X to C-H |
Reduction of saturated alkyl halides to alkanes |
Reduction of saturated alcohols and amines to alkenes |
Reduction of epoxides |
Reduction of ketones to alkenes |
Hydrogenolysis of allyl and benzyl halides and related compounds |
Reduction of agr;-substituted carbonyl compounds-CX-CO- to carbonyl compounds -CH-CO- |
Nonstabilized Carbanion Equivalents. |
Carbanions of alkali and alkaline earth cations |
synthesis and structural characterization / (i): |
selectivity of carbonyl addition reactions / (ii): |
Organoaluminum reagents |
Organocopper reagents |
Organo-titanium and organo-zirconium reagents |
Organochromium reagents |
Organo-zinc, -cadmium and -mercury reagents |
Organocerium reagents |
Samarium and ytterbium reagents |
Lewis acid carbonyl complexation |
Lewis acid promoted addition reactions of organometallic compounds |
Nucleophilic addition to imines and imine derivatives |
Nucleophilic addition to carboxylic acid derivatives |
Heteroatom-Stabilized Carbanion Equivalents |
Nitrogen stabilization |
Boron stabilization |
Sulfur stabilization |
The Benzoin and related reactions |
Silicon stabilization |
Selenium stabilization |
Transformation of the Carbonyl Group into Nonhydroxylic Groups |
Alkene synthesis |
Epoxidation and related processes |
Skeletal reorganizations: chain extension and ring expansion |
Alkylation of Carbon |
Alkylations of enols and enolates |
Alkylations of nitrogen-stabilized carbanions |
Alkylations of sulphur-and selenium-stabilized carbanions |
Alkylations of other heteroatom-stabilized carbanions |
Alkylations of nonstabilized carbanions |
Alkylations of vinyl carbanions |
Alkylations of alkynyl carbanions |
Friedel-Crafts alkylations |
Polyene cyclizations |
Transannular electrophilic cyclizations |
Coupling Reactions |
Coupling reactions between sp 3 carbon centers |
Coupling reactions between sp 3 and sp 2 carbon centers |
Coupling reactions between sp 2 carbon centers |
Coupling reactions between sp 2 and sp carbon centers |
Coupling reactions between sp carbon centers |
Pinacol coupling reactions |
Acyloin coupling reactions |
Kolbe reactions |
Oxidative coupling of phenols and phenol ethers |
Rearrangement Reactions |
Wagner-Meerwein rearrangements |
The Pinacol rearrangement |
Acid-catalyzed rearrangements of epoxides |
The semipinacol and other rearrangements |
Dienone-phenol rearrangements and related reactions |
Benzil-benzilic acid rearrangements |
The Favorskii rearrangement |
The Ramberg-Bauml;cklund rearrangement |
The Wolff rearrangement |
The Stevens and related rearrangements |
The Wittig rearrangement |
Other Carbon-Carbon Bond Forming Reactions |
Carbonylation and decarbonylation reactions |
Carbon-carbon bond formation by C-H insertion |