كتاب Organic Chemistry - Theory, Reactivity and Mechanisms in Modern Synthesis

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Organic Chemistry - Theory, Reactivity and Mechanisms in Modern Synthesis
With a Foreword by Robert H. Grubbs
Pierre Vogel , Kendall N. Houk

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Contents
Preface xv
Foreword xxix
Equilibria and thermochemistry
. Introduction
. Equilibrium-free enthalpy: reaction-free energy or Gibbs energy
. Heat of reaction and variation of the entropy of reaction (reaction entropy)
. Statistical thermodynamics
Contributions from translation energy levels
Contributions from rotational energy levels
Contributions from vibrational energy levels
Entropy of reaction depends above all on the change of the number of molecules between products
and reactants
Additions are favored thermodynamically on cooling, fragmentations on heating
. Standard heats of formation
. What do standard heats of formation tell us about chemical bonding and ground-state properties of
organic compounds?
Effect of electronegativity on bond strength
Effects of electronegativity and of hyperconjugation
?-Conjugation and hyperconjugation in carboxylic functions
Degree of chain branching and Markovnikov’s rule
. Standard heats of typical organic reactions
Standard heats of hydrogenation and hydrocarbation
Standard heats of C–H oxidations
Relative stabilities of alkyl-substituted ethylenes
Effect of fluoro substituents on hydrocarbon stabilities
Storage of hydrogen in the form of formic acid
. Ionization energies and electron affinities
. Homolytic bond dissociations; heats of formation of radicals
Measurement of bond dissociation energies
Substituent effects on the relative stabilities of radicals
?-Conjugation in benzyl, allyl, and propargyl radicals
. Heterolytic bond dissociation enthalpies
. . Measurement of gas-phase heterolytic bond dissociation enthalpies
. . Thermochemistry of ions in the gas phase
. . Gas-phase acidities
. Electron transfer equilibria
. Heats of formation of neutral, transient compounds
. . Measurements of the heats of formation of carbenes
. . Measurements of the heats of formation of diradicals
. . Keto/enol tautomerism
. . Heat of formation of highly reactive cyclobutadiene
. . Estimate of heats of formation of diradicals vi Contents
. Electronegativity and absolute hardness
. Chemical conversion and selectivity controlled by thermodynamics
. . Equilibrium shifts (Le Chatelier’s principle in action)
. . Importance of chirality in biology and medicine
. . Resolution of racemates into enantiomers
. . Thermodynamically controlled deracemization
. . Self-disproportionation of enantiomers
. Thermodynamic (equilibrium) isotopic effects
.A Appendix, Table .A. to Table .A.
References
Additivity rules for thermodynamic parameters and deviations
. Introduction
. Molecular groups
. Determination of the standard group equivalents (group equivalents)
. Determination of standard entropy increments
. Steric effects
Gauche interactions: the preferred conformations of alkyl chains
(E)- vs. (Z)-alkenes and ortho-substitution in benzene derivatives
. Ring strain and conformational flexibility of cyclic compounds
Cyclopropane and cyclobutane have nearly the same strain energy
Cyclopentane is a flexible cycloalkane
Conformational analysis of cyclohexane
Conformational analysis of cyclohexanones
Conformational analysis of cyclohexene
Medium-sized cycloalkanes
Conformations and ring strain in polycycloalkanes
Ring strain in cycloalkenes
Bredt’s rule and “anti-Bredt” alkenes
Allylic , - and , -strain: the model of banana bonds
. ??/?-, n/?-, ?/?-, and n/?-interactions
Conjugated dienes and diynes
Atropisomerism in , -dienes and diaryl compounds
??,?-Unsaturated carbonyl compounds
Stabilization by aromaticity
Stabilization by n(Z:)/?? conjugation
??/?-Conjugation and ??/?-hyperconjugation in esters, thioesters, and amides
Oximes are more stable than imines toward hydrolysis
Aromatic stabilization energies of heterocyclic compounds
Geminal disubstitution: enthalpic anomeric effects
Conformational anomeric effect
. Other deviations to additivity rules
. Major role of translational entropy on equilibria
Aldol and crotonalization reactions
Aging of wines
. Entropy of cyclization: loss of degrees of free rotation
. Entropy as a synthetic tool
. . Pyrolysis of esters
. . Method of Chugaev
. . Eschenmoser–Tanabe fragmentation
. . Eschenmoser fragmentation
. . Thermal , -eliminations
. . Retro-Diels–Alder reactions
.A Appendix, Table .A. to Table .A.
References Contents vii
Rates of chemical reactions
. Introduction
. Differential and integrated rate laws
Order of reactions
Molecularity and reaction mechanisms
Examples of zero order reactions
Reversible reactions
Parallel reactions
Consecutive reactions and steady-state approximation
Consecutive reactions: maximum yield of the intermediate product
Homogeneous catalysis: Michaelis–Menten kinetics
Competitive vs. noncompetitive inhibition
Heterogeneous catalysis: reactions at surfaces
. Activation parameters
Temperature effect on the selectivity of two parallel reactions
The Curtin–Hammett principle
. Relationship between activation entropy and the reaction mechanism
Homolysis and radical combination in the gas phase
Isomerizations in the gas phase
Example of homolysis assisted by bond formation: the Cope rearrangement
Example of homolysis assisted by bond-breaking and bond-forming processes: retro–carbonyl–ene
reaction
Can a reaction be assisted by neighboring groups?
. Competition between cyclization and intermolecular condensation
Thorpe–Ingold effect
. Effect of pressure: activation volume
Relationship between activation volume and the mechanism of reaction
Detection of change of mechanism
Synthetic applications of high pressure
Rate enhancement by compression of reactants along the reaction coordinates
Structural effects on the rate of the Bergman rearrangement
. Asymmetric organic synthesis
Kinetic resolution
Parallel kinetic resolution
Dynamic kinetic resolution: kinetic deracemization
Synthesis starting from enantiomerically pure natural compounds
Use of recoverable chiral auxiliaries
Catalytic desymmetrization of achiral compounds
Nonlinear effects in asymmetric synthesis
Asymmetric autocatalysis
. Chemo- and site-selective reactions
. Kinetic isotope effects and reaction mechanisms
Primary kinetic isotope effects: the case of hydrogen transfers
Tunneling effects
Nucleophilic substitution and elimination reactions
Steric effect on kinetic isotope effects
Simultaneous determination of multiple small kinetic isotope effects at natural
abundance
References
Molecular orbital theories
. Introduction
. Background of quantum chemistry
. Schr?dinger equation
. Coulson and Longuet-Higgins approach viii Contents
Hydrogen molecule
Hydrogenoid molecules: The PMO theory
. Hückel method
?-Molecular orbitals of ethylene
Allyl cation, radical, and anion
Shape of allyl ?-molecular orbitals
Cyclopropenyl systems
Butadiene
Cyclobutadiene and its electronic destabilization (antiaromaticity)
Geometries of cyclobutadienes, singlet and triplet states
Pentadienyl and cyclopentadienyl systems
Cyclopentadienyl anion and bishomocyclopentadienyl anions
Benzene and its aromatic stabilization energy
, -Dimethylidenecyclobutene is not stabilized by ?-conjugation
Fulvene
[N]Annulenes
Cyclooctatetraene
?-systems with heteroatoms
. Aromatic stabilization energy of heterocyclic compounds
. Homoconjugation
Homoaromaticity in cyclobutenyl cation
Homoaromaticity in homotropylium cation
Homoaromaticity in cycloheptatriene
Bishomoaromaticity in bishomotropylium ions
Bishomoaromaticity in neutral semibullvalene derivatives
Barrelene effect
. Hyperconjugation
Neutral, positive, and negative hyperconjugation
Hyperconjugation in cyclopentadienes
Nonplanarity of bicyclo[ ]hept- -ene double bond
Conformation of unsaturated and saturated systems
Hyperconjugation in radicals
Hyperconjugation in carbenium ions
Hyperconjugation in carbanions
Cyclopropyl vs. cyclobutyl substituent effect
. Heilbronner M?bius aromatic [N]annulenes
. Conclusion
References
Pericyclic reactions
. Introduction
. Electrocyclic reactions
Stereochemistry of thermal cyclobutene-butadiene isomerization: four-electron electrocyclic
reactions
Longuet-Higgins correlation of electronic configurations
Woodward–Hoffmann simplification
Aromaticity of transition states in cyclobutene/butadiene electrocyclizations
Torquoselectivity of cyclobutene electrocyclic reactions
Nazarov cyclizations
Thermal openings of three-membered ring systems
Six-electron electrocyclic reactions
Eight-electron electrocyclic reactions
. Cycloadditions and cycloreversions
Stereoselectivity of thermal [?? +?? ]-cycloadditions: Longuet-Higgins model Contents ix
Woodward–Hoffmann rules for cycloadditions
Aromaticity of cycloaddition transition structures
Mechanism of thermal [?? +?? ]-cycloadditions and [?? +?? ]-cycloreversions: , -diradical/zwitterion
intermediates or diradicaloid transition structures
Cycloadditions of allenes
Cycloadditions of ketenes and keteniminium salts
Wittig olefination
Olefinations analogous to the Wittig reaction
Diels–Alder reaction: concerted and non-concerted mechanisms compete
Concerted Diels–Alder reactions with synchronous or asynchronous transition states
Diradicaloid model for transition states of concerted Diels–Alder reactions
Structural effects on the Diels–Alder reactivity
Regioselectivity of Diels–Alder reactions
Stereoselectivity of Diels–Alder reactions: the Alder “endo rule”
?-Facial selectivity of Diels–Alder reactions
Examples of hetero-Diels–Alder reactions
, -Dipolar cycloadditions
Sharpless asymmetric dihydroxylation of alkenes
Thermal ( + + )-cycloadditions
Noncatalyzed ( + )- and ( + )-cycloadditions
Thermal higher order (m+n)-cycloadditions
. Cheletropic reactions
Cyclopropanation by ( + )-cheletropic reaction of carbenes
Aziridination by ( + )-cheletropic addition of nitrenes
Decarbonylation of cyclic ketones by cheletropic elimination
Cheletropic reactions of sulfur dioxide
Cheletropic reactions of heavier congeners of carbenes and nitrenes
. Thermal sigmatropic rearrangements
( , )-Sigmatropic rearrangement of carbenium ions
( , )-Sigmatropic rearrangements of radicals
( , )-Sigmatropic rearrangements of organoalkali compounds
( , )-Sigmatropic rearrangements
( , )-Sigmatropic rearrangements
( , )-Sigmatropic rearrangements
( , )-Sigmatropic rearrangements
( , )-Sigmatropic rearrangements
( , )-Sigmatropic rearrangements
. Fischer indole synthesis ( , -diaza-Cope rearrangement)
. Claisen rearrangement and its variants ( -oxa-Cope rearrangements)
. Aza-Claisen rearrangements ( -aza-Cope rearrangements)
. Overman rearrangement ( -oxa- -aza-Cope rearrangement)
. Thia-Claisen rearrangement ( -thia-Cope rearrangement)
. Cope rearrangements
. Facile anionic oxy-Cope rearrangements
. Acetylenic Cope rearrangements
. Other hetero-Cope rearrangements
. Dyotropic rearrangements and transfers
Type I dyotropic rearrangements
Alkene and alkyne reductions with diimide
Type II dyotropic rearrangements
. Ene-reactions and related reactions
Thermal Alder ene-reactions
Carbonyl ene-reactions
Other hetero-ene reactions involving hydrogen transfers x Contents
Metallo-ene-reactions
Carbonyl allylation with allylmetals: carbonyl metallo-ene-reactions
Aldol reaction
Reactions of metal enolates with carbonyl compounds
References
Organic photochemistry
. Introduction
. Photophysical processes of organic compounds
UV–visible spectroscopy: electronic transitions
Fluorescence and phosphorescence: singlet and triplet excited states
Bimolecular photophysical processes
. Unimolecular photochemical reactions of unsaturated hydrocarbons
Photoinduced (E)/(Z)-isomerization of alkenes
Photochemistry of cyclopropenes, allenes, and alkynes
Electrocyclic ring closures of conjugated dienes and ring opening of cyclobutenes
The di-?-methane (Zimmerman) rearrangement of , -dienes
Electrocyclic interconversions of cyclohexa- , -dienes and hexa- , , -trienes
. Unimolecular photochemical reactions of carbonyl compounds
Norrish type I reaction (?-cleavage)
Norrish type II reaction and other intramolecular hydrogen transfers
Unimolecular photochemistry of enones and dienones
. Unimolecular photoreactions of benzene and heteroaromatic analogs
Photoisomerization of benzene
Photoisomerizations of pyridines, pyridinium salts, and diazines
Photolysis of five-membered ring heteroaromatic compounds
. Photocleavage of carbon–heteroatom bonds
Photo-Fries, photo-Claisen, and related rearrangements
Photolysis of , -diazenes, H-diazirines, and diazo compounds
Photolysis of alkyl halides
Solution photochemistry of aryl and alkenyl halides
Photolysis of phenyliodonium salts: formation of aryl and alkenyl cation intermediates
Photolytic decomposition of arenediazonium salts in solution
. Photocleavage of nitrogen—nitrogen bonds
Photolysis of azides
Photo-Curtius rearrangement
Photolysis of geminal diazides
Photolysis of , , -triazoles and of tetrazoles
. Photochemical cycloadditions of unsaturated compounds
Photochemical intramolecular ( + )-cycloadditions of alkenes
Photochemical intermolecular ( + )-cycloadditions of alkenes
Photochemical intermolecular ( + )-cycloadditions of dienes and alkenes
Photochemical cycloadditions of benzene and derivatives to alkenes
Photochemical cycloadditions of carbonyl compounds
Photochemical cycloadditions of imines and related C=N double-bonded compounds
. Photo-oxygenation
Reactions of ground-state molecular oxygen with hydrocarbons
Singlet molecular oxygen
Diels–Alder reactions of singlet oxygen
Dioxa-ene reactions of singlet oxygen
( + )-Cycloadditions of singlet oxygen
, -Dipolar cycloadditions of singlet oxygen
Nonpericyclic reactions of singlet oxygen
. Photoinduced electron transfers Contents xi
. . Marcus model
. . Catalysis through photoreduction
. . Photoinduced net reductions
. . Catalysis through photo-oxidation
. . Photoinduced net oxidations
. . Generation of radical intermediates by PET
. . Dye-sensitized solar cells
. Chemiluminescence and bioluminescence
. . Thermal isomerization of Dewar benzene into benzene
. . Oxygenation of electron-rich organic compounds
. . Thermal fragmentation of , -dioxetanes
. . Peroxylate chemiluminescence
. . Firefly bioluminescence
References
Catalytic reactions
. Introduction
. Acyl group transfers
Esterification and ester hydrolysis
Acid or base-catalyzed acyl transfers
Amphoteric compounds are good catalysts for acyl transfers
Catalysis by nucleofugal group substitution
N-heterocyclic carbene-catalyzed transesterifications
Enzyme-catalyzed acyl transfers
Mimics of carboxypeptidase A
Direct amide bond formation from amines and carboxylic acids
. Catalysis of nucleophilic additions
Catalysis of nucleophilic additions to aldehydes, ketones and imines
Bifunctional catalysts for nucleophilic addition/elimination
?- and ?-Nucleophiles as catalysts for nucleophilic additions to aldehydes and ketones
Catalysis by self-assembled encapsulation
Catalysis of , -additions (conjugate additions)
. Anionic nucleophilic displacement reactions
Pulling on the leaving group
Phase transfer catalysis
. Catalytical Umpolung C—C bond forming reactions
Benzoin condensation: Umpolung of aldehydes
Stetter reaction: Umpolung of aldehydes
Umpolung of enals
Umpolung of Michael acceptors
Rauhut–Currier reaction
Morita–Baylis–Hillman reaction
Nucleophilic catalysis of cycloadditions
Catalysis through electron-transfer: hole-catalyzed reactions
Umpolung of enamines
Catalysis through electron-transfer: Umpolung through electron capture
. Br?nsted and Lewis acids as catalysts in C—C bond forming reactions
Mukaiyama aldol reactions
Metallo-carbonyl-ene reactions
Carbonyl-ene reactions
Imine-ene reactions
Alder-ene reaction
Diels–Alder reaction
Br?nsted and Lewis acid-catalyzed hetero-Diels-Alder reactions xii Contents
Acid-catalyzed ( + )-cycloadditions
Lewis acid catalyzed ( + )- and ( + )-cycloadditions
Lewis acid promoted ( + )-cycloadditions
. Bonding in transition metal complexes and their reactions
The ?-complex theory
The isolobal formalism
?-Complexes of dihydrogen
?-Complexes of C—H bonds and agostic bonding
?-Complexes of C—C bonds and C—C bond activation
Reactions of transition metal complexes are modeled by reactions of organic chemistry
Ligand exchange reactions
Oxidative additions and reductive eliminations
?-Insertions/?-eliminations
?-Insertions/?-eliminations
?-Cycloinsertions/?-cycloeliminations: metallacyclobutanes, metallacyclobutenes
Metallacyclobutenes: alkyne polymerization, enyne metathesis, cyclopentadiene synthesis
Metallacyclobutadiene: alkyne metathesis
Matallacyclopentanes, metallacyclopentenes, metallacyclopentadienes: oxidative cyclizations
(?-cycloinsertions) and reductive fragmentations (?-cycloeliminations)
. Catalytic hydrogenation
Heterogeneous catalysts for alkene, alkyne, and arene hydrogenation
Homogeneous catalysts for alkene and alkyne hydrogenation
Dehydrogenation of alkanes
Hydrogenation of alkynes into alkenes
Catalytic hydrogenation of arenes and heteroarenes
Catalytic hydrogenation of ketones and aldehydes
Catalytic hydrogenation of carboxylic acids, their esters and amides
Hydrogenation of carbon dioxide
Catalytic hydrogenation of nitriles and imines
Catalytic hydrogenolysis of C–halogen and C–chalcogen bonds
. Catalytic reactions of silanes
Reduction of alkyl halides
Reduction of carbonyl compounds
Alkene hydrosilylation
. Hydrogenolysis of C—C single bonds
. Catalytic oxidations with molecular oxygen
. . Heme-dependent monooxygenase oxidations
. . Chemical aerobic C—H oxidations
. . Reductive activation of molecular oxygen
. . Oxidation of alcohols with molecular oxygen
. . Wacker process
. Catalyzed nucleophilic aromatic substitutions
. . Ullmann–Goldberg reactions
. . Buchwald–Hartwig reactions
References
Transition-metal-catalyzed C—C bond forming reactions
. Introduction
. Organic compounds from carbon monoxide
Fischer–Tropsch reactions
Carbonylation of methanol
Hydroformylation of alkenes
Silylformylation
Reppe carbonylations Contents xiii
Pd(II)-mediated oxidative carbonylations
Pauson–Khand reaction
Carbonylation of halides: synthesis of carboxylic derivatives
Reductive carbonylation of halides: synthesis of carbaldehydes
Carbonylation of epoxides and aziridines
Hydroformylation and silylformylation of epoxides
. Direct hydrocarbation of unsaturated compounds
Hydroalkylation of alkenes: alkylation of alkanes
Alder ene-reaction of unactivated alkenes and alkynes
Hydroarylation of alkenes: alkylation of arenes and heteroarenes
Hydroarylation of alkynes: alkenylation of arenes and heteroarenes
Hydroarylation of carbon-heteroatom multiple bonds
Hydroalkenylation of alkynes, alkenes, and carbonyl compounds
Hydroacylation of alkenes and alkynes
Hydrocyanation of alkenes and alkynes
Direct reductive hydrocarbation of unsaturated compounds
Direct hydrocarbation via transfer hydrogenation
. Carbacarbation of unsaturated compounds and cycloadditions
Formal [?? +?? ]-cycloadditions
( + )-Cycloadditions
Ohloff–Rautenstrauch cyclopropanation
[?? +?? ]-Cycloadditions
( + )-Cycloadditions
( + )-Cycloadditions
( + )-Cycloadditions
( + + )-Cycloadditions
[?? +?? ]-Cycloadditions of unactivated cycloaddents
( + + )-Cycloadditions
( + )-Cycloadditions
( + + )-Cycloadditions
( + )-Cycloadditions
( + )-Cycloadditions
( + )-Cycloadditions
( + + )-Cycloadditions
( + )-Cycloadditions
( + + + )-Cycloadditions
( + + )-Cycloadditions
( + )-Cycloadditions
Further examples of high-order catalyzed cycloadditions
Annulations through catalytic intramolecular hydrometallation
Oxidative annulations
. Didehydrogenative C—C-coupling reactions
Glaser–Hay reaction: oxidative alkyne homocoupling
Oxidative C—C cross-coupling reactions
Oxidative aryl/aryl homocoupling reactions
Oxidative aryl/aryl cross-coupling reactions
TEMPO-cocatalyzed oxidative C—C coupling reactions
Oxidative aminoalkylation of alkynes and active C—H moieties
. Alkane, alkene, and alkyne metathesis
Alkane metathesis
Alkene metathesis
Enyne metathesis: alkene/alkyne cross-metathesis
Alkyne metathesis
. Additions of organometallic reagents xiv Contents
Additions of Grignard reagents
Additions of alkylzinc reagents
Additions of organoaluminum compounds
Additions of organoboron, silicium , and zirconium compounds
. Displacement reactions
Kharash cross-coupling and Kumada–Tamao–Corriu reaction
Negishi cross-coupling
Stille cross-coupling and carbonylative Stille reaction
Suzuki–Miyaura cross-coupling
Hiyama cross-coupling
Tsuji–Trost reaction: allylic alkylation
Mizoroki–Heck coupling
Sonogashira–Hagihara cross-coupling
Arylation of arenes(heteroarenes) with aryl(heteroaryl) derivatives
?-Arylation of carbonyl compounds and nitriles
Direct arylation and alkynylation of nonactivated C—H bonds in alkyl groups
Direct alkylation of nonactivated C—H bonds in alkyl groups
References
Index

Index
A
aaptosine ,
ab initio Hartree–Fock (HF) calculations
absolute asymmetric synthesis ,
absolute electronegativity
absolute hardness – ,
absolute softness
absorbance
absorption complex ,
absorption on crystalline quartz
acetaldehyde , , , , , , ,
,

acetamide , , , ,
acetic acid , , , , ,
, – ,
acetic anhydride ,
acetone , , , , , , , , , ,
, – , – ,
,
,
, , , ,
,
acetophenone
-acetoxy- and -chlorocyclopentadiene
acetoxypyranone
acetyl chloride , ,
acetylenes, Pd-catalyzed carbonylation of
acetylide anions
achiral alkene
achiral allenamide
acid catalyzed cationic cyclization
acid-catalyzed ( + )-cycloadditions ,
acid or base-catalyzed acyl transfers –
acrolein ,
acrylic derivative , ,
acrylic ester ,
, , , , ,
acrylonitrile , ,
, ,
activation enthalpy , –
,

activation entropy , –

activation entropy and reaction mechanism
– Cope rearrangement
– gas phase
– – homolysis and radical combination –
– – isomerizations –
– neighboring group directing effects
– retro-carbonyl-ene reaction –
activation parameters
– Curtin–Hammett principle –
– temperature effect, two parallel reactions
acyclic ??,??- and ??,??-enones ,
acyclic alkylaminocarbene
acyclic diene ,
acyclic , -dienes
acyclic dithiosilylene
acyclic peroxides
( , )-acyloxy shifts
acyl group transfers , –
acyl transfers – , – ,
, -(adamant- -yl)- H-diazirine
(adamant- -yl)nitrene
addition
– of alkylzinc reagents –
– of Grignard reagents –
– of organoaluminum compounds –
– of organoboron –
– of silicium –
– of zirconium compounds –
addition–elimination mechanism
,
additivity rules
– ??,??-unsaturated carbonyl compounds
– atropisomerism in , -dienes and diaryl compounds
–
– conjugated dienes and diynes –
– molecular groups
– – additivity of, molecular properties
additivity rules (contd.)
– – group additivity methods
– – toluene formation
– oximes
– standard entropy increments –
– standard group equivalents –
– steric effects
– – allylic , -strain ,
– – anti-Bredt alkenes –
– – Bredt’s rule ,
– – cyclobutane –
– – cyclohexane –
– – cyclohexanones –
– – cyclohexene
– – cyclopentane ,
– – cyclopropane
– – (E)- vs.(Z)-alkenes
– – Gauche interactions –
– – medium-sized cycloalkanes –
– – polycycloalkanes, conformations and ring strain

– – ring strain and conformational flexibility ,
– – ring strain in cycloalkenes
– translational entropy on equilibria
– – ageing of wines ,
– – aldol reaction –
– – and crotonalization reactions –
adiabatic transition
adsorption on achiral surfaces
aerobic C–H oxidations –
aerobic didehydrogenative coupling reaction ,

ageing of wines –
alcohols oxidation with molecular oxygen –
alcoholysis ,
aldehydes – , , , , , , – ,
, – , – ,
, – , – ,
, – , – ,
,
, – , – , – , – ,
– – ,
, –
Alder endo rule
Alder-ene-reactions ,
– , , –
– of unactivated alkynes and alkenes
aldol and crotonalization reactions – ,
aliphatic alkylation
alkanes, dehydrogenation of
alkenes
– enantioselective carbomagnesiation
– heterogeneous catalysts for –
– homogeneous catalysts for –
– hydroacyclation of
– hydroarylation of –
– hydrocyanation of –
– hydroformylation of
– hydrosilylation –
– intermolecular hydroacylation of ,
– isomerization
– metallacarbation
– metathesis –
– Pd(II)-mediated oxidative carbonylations –
alkene–silver cation complex
-alkenylallenyl silyl ethers ,
alkenylbenzocyclobutenes
alkenyl cation intermediates –
-alkenylcyclohexa- , -dienes
alkenylidenecyclopropanes
alkenyl mechanism ,
-alkoxy- -acyloxy- , -dienes
-alkoxyalkyllithium
-alkoxy- and -halogenophospholes
-alkoxy- , -bis(silyloxy)- , -butadienes
alkoxy radicals , ,
alkoxy-substituted aldehydes
alkyl ??-D-glucopyranosides
alkylaluminum halides
alkyl arylaminoacetate
alkyl aryloxyacetate
alkylate technology
alkylation, of alkanes –
alkyl azides
alkyl disubstituted silylene
alkyl halides
– photolysis of –
– reduction of –
alkylidene carbenes
alkylidene- H-pyran (E)
-alkylideneoxetane
alkyl iodides , , , , ,
, , ,
alkylithium ,
alkyl mechanism ,
alkyl/peroxyl , -diradical ,
-alkyl- -phenyl- H-diazirines
alkyl-substituted alkenes , , , , , ,

alkyl-substituted alkynes , , ,
alkyl-substituted , -dioxetane
alkylzinc reagents, addition of –
alkyne/alkene cross-metathesis ,
alkynes
– Cu +-catalyzed oxidative homocoupling of
– heterogeneous catalysts for –
– hydroacylation of
– hydroarylation of Index
– hydrocyanation of –
– hydroformylation of
– hydrogenation, homogeneous catalysts for –
– hydrogenation of –
– metathesis – , –
– oxidative aminoalkylation of –
– palladium-catalyzed hydroalkenylation of
– polymerization –
– Ru-catalyzed ( + )-cycloadditions of
– silylformylation –
– Zr-catalyzed ethylalumination
– Zr-catalyzed methylalumination
allenamides ,
allene–alkene intermediates
allene cycloaddition –
allowed ??(CO) ? ?? *(CO) transition
allowed thermal [?? c] electrocyclization
allowed transitions
allylcyclopropane
allylic alcohol
,
, ,
allylic alkylation –
allylic boron compounds
allylic cations , , ,
allylic hydroperoxides ,
allylic hydroxy group
allylic , -strain
allyl methyl thioether into methyl (E)-prop- -en- -yl
thioether
allyl/peroxyl diradical
allyl ??-molecular orbitals
allyl (prop- -enyl) ethers
allylsilanes synthetic
??,???-dibromoketones
??-amino acids
??-arylation of carbonyl compounds and nitriles
??,??-epoxyketones
??,??-unsaturated aldehydes , ,
??,??-unsaturated carbonyl compounds ,
,
??,??-unsaturated nitriles , ,
??-chlorocyclohexanone
(–)-??-cuprarenone
??-cuprarenone/??-cycloeliminations
??-diazocarbonyl compounds
??-diazocarboxamides
??-diazoketones
??-eliminations
??-epimerization
??-halogenation of ketones
??-iminocarbonitriles
??-iminocycloalkanecarbonitriles
??-insertion/??-eliminations
??-ionone
??-ketoaziridines
??-ketoepoxides
??-methoxydibenzyl ketone
??-methylbenzyl azide
??-pyridones
??-pyrones ,
??-santonin
??-silyl stabilized carbanions
??-stannylated thionocarbamates, alkynylation of
ambimodal transition states
amines
– and carboxylic acids ,
-aminoadamantane
amino-alcohols ,
aminoalkyl radical , ,
-amino-, -aminophenones
aminoarenethiolate
-aminodiene ,
-aminopenta- , -dienal
aminophenols
-aminophthalate salt
ammonium detergents
amphoteric compounds
, - and , -dihydroarenes
, -, , - and , -dimethylbenzene
-, -, and -methylpyrimidines
, , - and , , -triphenyltrichlorobenzene
Anelli–Montanari protocol
anharmonicity ,
anhydride formation
anilines , , , , ,
, ,
annulation reaction , ,
annulenes – ,
anodic oxidation of N-aminophthalimide
antarafacial [?? a+?? s]-cheletropic additions
antarafacial/suprafacial [?? a+?? s]-cycloaddition
anthelmintic (toxic) drug
anthracene- , -dicarbonitrile (DCA)
anthracenemagnesium
anti-AIDS
antiaromatic cyclopentadienone
antiaromaticity , ,
–
antibonding MO

anti-Bredt alkenes
anti-flu
anti-Markovnikov hydrosilylations
anti-Markovnikov products ,
antimicrobial agents
-anti-norbornenyl acetate
antiperiplanar conformation Index
antiperiplanar conformers
anti stereoisomers
anti-stereotriads
(+)-Aphanamol I
appearance potential or appearance energy AP(A+)
arene- and heteroaromatic diazonium salts
areneboronic acids, decabonylative coupling of
arenecarbonitrile , ,
arenediazonium anthracenesulfonates
arenediazonium salts – ,
arene hydrogenation –
arenepolynitriles
arene radical cation intermediates
arenes and heteroarenes
– alkenylation of –
– alkylation of –
arenesulfonanilides
argentoazomethine ylide
aromatic compounds , , , ,
,
aromatic electrophilic substitutions
–
aromaticity
– of benzene
– of cycloaddition transition structure
– of transition states in cyclobutene/butadiene
electrocyclizations
aromaticity/antiaromaticity ,
aromatic oxalic esters
aromatic stabilization energy (ASE) , –

– benzene
– of heterocyclic compounds ,
aromatic thiones
aroyl-??-cyclodextrins
Arrhenius activation energies
Arrhenius equation
aryl and alkenyl halides, solution photochemistry of
–
arylation of arenes(heteroarenes)
arylboronates
aryl carbamates
aryl chlorides , ,
– catalytic dehalogenation of
– Pd-catalyzed aminocarbonylation
– trifluoromethylation of
aryldiazenyl radical
aryldiazonium salt , ,
-aryl- , -diphenylimidazoles
arylimines ,
aryl iodides , , ,
, , , , , , , – ,

aryliodonium ylides
aryl ketones ,
arylnitrenes ,
arylnitrenyl
-aryl- -oxazolines
aryloxyacetones
(arylphosphine)copper(I) halides
aryl radical , , ,
aryl-substituted alkenes , , ,
(±)-ascaridole
ascorbic acid
associative mechanism

associative processes
asymmetric alkene + ketene cycloaddition
asymmetric alkene metathesis
asymmetric alkylfluoration
asymmetric carboalumination
asymmetric carbomagnesiation
asymmetric catalytic dihydrogenation ,

asymmetric conjugate additions , ,
,
asymmetric cyclopropanation , –
asymmetric diastereoselective propargylations
asymmetric Hosomi–Sakurai reaction
asymmetric intramolecular enolate arylations
asymmetric Mannich-type reaction
asymmetric organocatalysis
asymmetric Reformatsky reaction ,
asymmetric synthesis
– autocatalysis –
– catalytic desymmetrization, achiral compounds
–
– definition
– deracemization , –
– enantiomerically pure natural compounds , – ,
–
– Kiliani–Fischer aldose chain elongation method
– kinetic resolution –
– nonlinear effects –
– parallel kinetic resolution –
– recoverable chiral auxiliaries –
asymmetric version, of cyclopropanation
asynchronous transition structures – ,

atomic orbitals (AO) – ,
atorvastatin
atropisomerism , -dienes and diaryl compounds,
–
atroposelectivity
autocatalysis –
auto-oxidation of lophine
average heat of reaction
average nuclear frequency factor
Avogadro constant , Index
Avogadro’s number ,
-aza and -azabicyclo[ ]hexa- , -dienes
-azabicyclo[ ]hex- -ene
-azabicyclo[ ]hex- -en- -exo-ol
-azabicyclo[ ]hexenyl cation intermediate
-azabornane
-azacyclohepta- , , , -tetraene
aza-Diels–Alder reaction
-aza- , -dienes ,
aza-di-??-methane
aza-di-??-rearrangement
-azahepta- , , , -tetraenes
aza-ortho-xylydenes
aza-prismanes
azaruthenabicyclo[ ]heptatriene
azepins
azicemicins
azides, photolysis of –
-azidoadamantane
azidoalcohols ,
azidopyridines
azinomycins
aziridination by ( + )-cheletropic addition of nitrenes
–
aziridines –
– , , , , ,
– carbonylation of
azoles , , , ,
azomethine ylides
azulene ,
B
back electron transfer
Back strain (B-strain) , ,
B?ckvall’s ruthenium catalyst
Baeyer strain –
Baeyer–Villiger oxidation
Baker’s yeast ,
Balz–Schiemann reaction
banana bond (?? bonds)
,
barrelene
– derivative
– effect ,
base-catalyzed hydrolysis of esters
bathochromic shift
Bayer strain (angle strain)
Beer–Lambert law ,
Beller’s reductive carbonylation, of aryl and heteroaryl
bromides
Bell–Evans–Polanyi (BEP) theory ,
, – ,
,
bench-stable compounds
Benson’s group additivity method ,
benzaldehyde ,
,
, , ,
benzazirine
benzene , , , , , , ,
,
– aromatic stabilization energy (ASE)
– Dewar , –
–
– direct photo-oxidation of
– Hückel method
– photoisomerization of –
– thermal isomerization of Dewar benzene into
–
benzene- , -diyl diradical ,
benzene- , -diyl diradical
benzenesulfonylnitrene
benzene- , , , -tetracarbonitrile ,
benzobicyclo[ ]hepta- , -diene
benzo[c]cycloheptatriene
benzocyclobutenes , – ,
, , ,
benzoic acid , ,
benzoin condensation – ,
benzonitrile
benzophenone
,
benzophenone O-oxide
, ?, , ?-benzophenonetetracarboxylic dianhydride

benzothiazol- -yl sulfones
benzvalene – ,
-(benzylamino)adamantane
-benzyl- , -dihydronicotinamide
benzyl-protected exoglycal
Bergman rearrangement , –
Bertrand’s carbene
Bertrand’s phosphinosilylcarbene
??-anomers
??-arylketones
??,??-trehalose (??-D-glucopyranosyl-( ? ?)-
??-D-glucopyranose)
??-bromohydroperoxide
??-carotene ,
??-chloroalkyl radicals
??-cholestanol
(–)-??-citronellol
??-cycloeliminations ,
??-cycloinsertions ,
??,??-unsaturated iminium triflate
??,??-unsaturated ketones ,
??-haloalkyl radicals
??-hydroxyacetal Index
??-hydroxy and ??-aminoketones
??-hydroxy carbonyl compounds
betaine/lithium salt complexes
betaines ,
??-insertion/??-elimination
?? -ketosulfones
??-lactams –
,
??-lactones ,
??-naphthols
– enantioselective oxidative homocoupling
– oxidative cross-coupling of
??-naphthylamine, oxidative cross-coupling of
??-pinene ,
??-silicon effect
??-silylalcoholates
??-silyl effect ,
??-silyloxyaldehydes
??-stannyl effect ,
??-sultine
biaryl catalyst
,
, , , , , , , , ,
, ,
biaryl products , , , ,

bicyclic azocines
bicyclic , -dienes
bicyclo[ ]butanes ,
bicyclo[ ]hepta- , -dienes
bicyclo[ ]hepta- , -dien- -one
bicyclo[ ]hept- -ene double bond
bicyclo[ ]hept- -ene gives
(Z,Z)-cyclohepta- , -diene
bicyclo[ ]hexa- , -diene
bicyclo[ ]hexane
bicyclo[ ]hexane
bicyclo[ ]hex- -ene
bicyclo[ ]hex- ( )-ene
bicyclo[ ]hex- -ene
bicyclo[ ]hex- -ene
bicyclo[ ]hex- -en- -ones
bicyclo[ ]hex- -en- -yl cation
bicyclo[n ]alkenes
bicyclo[ ]non- -ene
bicyclo[ ]octa- , -dienes
bicyclo[ ]octa- , , -triene
bicyclo[ ]oct- -ene
bicyclo[ ]pent- -ene
Bielawski’s diaminocarbene[ ]ferrocenophane
bifunctional catalyst ,
Bigeleisen treatment
bimolecular diffusion rate constant
bimolecular photophysical processes –
bimolecular reactions ,

BINAP , , , ,
binding energy ,
BINOL , ,
biocatalysts ,
bioluminescence (BL) ,
– firefly –
– oxygenation of electron-rich organic compounds
–
– peroxylate chemiluminescence
– thermal fragmentation of , -dioxetanes –
– thermal isomerization of Dewar benzene into
benzene –
bioluminescent imaging (BLI)
biomass , , , ,
bipyramidal transition state
bis(diazirine)
, -bis(chloromethyl)benzene
, -bis(chloromethyl)benzene
, -bis(chloromethyl)benzene
, -bis(t-butyl)bicyclo[ ]butane
, -bis(t-butyl)butadiene
, -, , -, and , -bis(chloromethyl)naphthalenes
bisenone
bishomoaromaticity
– in bishomotropylium ions –
– in neutral semibullvalene derivatives –
bishomoaromatic stabilization energy ,
bishomobenzene derivative
bishomocyclopentadienyl anions –
bishomotropylium ions –
, -bishomotropylium ions
bis[(methoxy)dimethyl]disilane
bis( , , -trichlorophenyl) oxalate
bisphenol A ( , -di( -hydroxyphenyl)propane)
bis(diazomethyl)silane
, -bis( -oxazolinyl)-( , -tert-butyl- , -dimethyl)- Hxanthenes
bite angle , , – ,
blood-brain barrier
blue luminescence
boat-like transition structure ,
Boche’s kinetic measurements
Bode’s asymmetric synthesis
Bode’s enantioselective synthesis
Boltzmann constant
Boltzmann–Planck equation
Boltzmann relationship ,
bond-coupled electron transfer (BCET)
bond dissociation energies , , – , , , – ,
,
bond dissociation enthalpies , ,
bond lengths – , Index
bonding MO
bond lengths, sulfides
bond stretching anharmonicity
Born–Haber cycles ,
Born–Oppenheimer approximation ,
Bouveault–Blanc reduction
BP Chemicals
branched alkenes
Brassard-type diene
Bredt’s rule –
Breit’s diphosphine ligands
Breslow intermediate
Breslow’s mechanism
bridged annulenes
bromonium ions
Br?nsted acid-mediated Nazarov cyclization
( , )-Brook rearrangement ,
Bucherer–Bergs reaction
Büchner reaction
Buchwald–Hartwig reactions , – ,
bulky ester derivatives
bulky
, , , , , -hexamethyl- , -dimethylidenecyclopentane

bulky Lewis acid catalysts
bullvalene
butadiene , , , ,
, , , , –
butadiene ? bicyclo[ ]butane
buta- , -diene
butadiene + ethylene ? hex- -ene- , -diyl diradical

butadiene hydrocyanation mechanism
C
cacodyl oxide
Cahn–Ingold–Prelog (CIP) rule , ,
calorimetry , , ,
cantharidin ,
CaO
•(H O )
carbaldehydes, synthesis of
carbanion PhMe
C–
carbanions – , , –
, –
carbazole
carbene limiting structure
carbene mechanism ,
carbenemetal complexes ,
carbenes , , ,
–
, , , , , ,

carbenium ions
– clock
– hyperconjugation in
– intermediates
– ( , )-sigmatropic rearrangement of –
carboalumination
carbon-heteroatom multiple bonds, hydroarylation of
,
carbonitriles ,
, , , , ,
carbon monoxide
– carbaldehydes –
– carboxylic derivatives –
– Fischer–Tropsch reactions –
– hydroformylation and silylformylation
– hydroformylation of alkenes –
– Pauson–Khand reaction –
– Reppe carbonylations –
– silylformylation –
carbonylations
– of ??,??-unsaturated imines
– of aryl arenesulfonates and mesylates
– of epoxides and aziridines –
– of halides
– of methanol –
– Pd(II)-mediated oxidative –
– Reppe carbonylations
carbonyl compounds reduction
carbonyl–ene reactions
carbonyl oxides
carbonyl ylides
carboxylic derivatives, synthesis of
carboxylic esters , ,
, , , , , ,
carboxypeptidase A
Carroll reaction
Carr–Parrinello method
carvone camphor
Cassar–Dieck–Heck alkynylation
Castro’s reagent
catalysis through photo-oxidation –
catalysis through photoreduction – ,
catalysts, of (Z)-stereoselective alkene metatheses
catalytic asymmetric cyclopropanations ,
catalytic asymmetric nitroso-Diels–Alder reaction
catalytic cycles, for iridium-catalyzed methanol
carbonylation
catalytic enantioselective synthesis
catalytic hydrogenation ,
– of arenes and heteroarenes
– of carbon dioxide –
– of carboxylic acids –
– of ketones and aldehydes –
– of nitriles and imines –
– their esters and amides –
catalytic hydrogenation of alkenes – Index
catalytic hydrogenation of alkynes into alkenes
catalytic oxidations with molecular oxygen –
catalyzed asymmetric Diels–Alder reaction
catalyzed asymmetric Nazarov cyclizations
catalyzed hydrocarbation, of unsaturated compounds

Catellani cascade reaction
CativaTM
C
-axis of symmetry
C—C bond forming reactions , – ,
, –
C–chalcogen bonds
CC single bonds, hydrogenolysis of ,
CF
substituents
chair ? chair interconversion
chair-shape , -dimethylidenecyclohexane
C–halogen bonds
change in enthalpy/heat of reaction
change in entropy/reaction entropy
charge transfer absorption
charge transfer complex
,
charge transfer configuration , ,
,
C–H bond, methane
chelation-assisted hydroarylations
( + )-cheletropic addition
( + )-cheletropic addition
cheletropic elimination , –

cheletropic reactions
– aziridination by ( + )-cheletropic addition of
nitrenes –
– cyclopropanation by ( + )-cheletropic reaction of
carbenes –
– decarbonylation of cyclic ketones by cheletropic
elimination –
– of heavier congeners of carbenes and nitrenes
–
– sulfur dioxide –
chemical conversion
chemically initiated electron-exchange luminescence
(CIEEL)
chemical quenching
chemiluminescence (CL)
– firefly –
– oxygenation of electron-rich organic compounds
–
– peroxylate chemiluminescence
– thermal fragmentation of , -dioxetanes –
– thermal isomerization of Dewar benzene into benzene
–
chemoselectivity
, , ,
Chevron process
chiral acid ,
chiral acid catalyst ,
,

chiral amplification ,
chiral anion phase-transfer (CAPT)
chiral auxiliary , – , – ,

chiral base , ,
,
chiral base catalyst ,
,
chiral cobalt(II) complex
chiral diaminocarbene catalyst ,
,
chiral diene ligand
chirality transfer , – ,
chiral menthyloxyfuranone
chiral oxazolidinethiones
chiral photochemistry
chiral surfaces ,
chiral tertiary amines
-chloroallyl cation intermediate
-chloro- -isopropyldiazirine
-(chloromethyl)benzyl radical
chlorophyll ,
chloroprene ,
-chloro- -propyldiazirine
C—H nucleophiles
chromatographic separation methods
Chugaev method
chymotrypsin
cis- and trans- , -diaryloxiranes
cis- and trans- , -diphenyl- , -dimethyldioxetane
cis- and trans- -oxabicyclo[ ]nonane
cis- and trans- -phenylcyclopentyl chloride
cis-bicyclo[ ]hept- -en- -one
cis,cis- , , -trimethylcyclohexane- , , -tricarboxylic
acid
cis-cyclopent- -ene- , -diol
cis-cyclopropanes
cis- , -diarylethylenes
cis- , -dideuterioacrylonitrile
cis-diepoxides
cis- , -dimethylcyclobutene ,
cis- , -dimethylcyclohexa- , -diene
cis- , -dimethylcyclopent- -enone
cis- , -diphenyl- , , -dioxazolidine
, -cis-disubstituted ??-lactams
cis- , -dithienylethylenes
cis- , -divinylcyclobutane ,
cis-effect
C-isotrehalose , Index
cis rule
cis- , , , -tetrachloro- , , , -tetraphenyltricyclo
[ . , ]octa- , -diene
cis- , , , -tetramethylcyclobutene
C-labeled bromoalkene
Claisen-type products
C-linked disaccharide
Coates’ mechanism, of epoxide carbonylation
Co
(CO) -catalyzed hydroformylation, of epoxides

CO
fixation ,
collisional efficiencies
collision-induced dissociation: CID
collisions with jets
combinatorial ligand library generation
common ion effect
competitive inhibition
competitive radical and ionic reactions
concentrations of products
concerted and synchronous [?? s+?? s]-cycloaddition

concerted anionic suprafacial ( , )-sigmatropic
rearrangement
concerted asynchronous mechanisms ,

concerted ( + )-cycloaddition
concerted Diels–Alder reactions –
concerted pericyclic reactions ,
concerted [?? s+?? a]-cycloadditions
concerted reactions , ,
,
concerted suprafacial ( , )-methyl sigmatropic
rearrangement
concurrent E/Z isomerization, of carbonyl ylides
condensation of tannins
conformational anomeric effects – ,

conglomerates ,
Conia-ene reaction ,
conical intersection ,
conjugate base ,
, ,
,
conjugated cyclohexenones
conjugated dienes
, – ,
,
– and diynes –
conjugation stabilization energy – ,
conjugation, with a triple C?C bond
conrotatory C—C ring opening of the oxirane
conrotatory electrocyclic reactions
conrotatory mode – , – ,
conrotatory [?? C] isomerization –
conrotatory ?? electron cyclization
consecutive irreversible reactions ,
contrasteric effects ,
coordinating solvents
Cope rearrangement ,
, – ,

copper(I)acetylide
copper carbenoid
copper-catalyzed carbene transfer
Corey–Chaykovsky reaction
Corey’s general synthesis of prostaglandins
corner-cutting tunneling effect
corner-protonated cyclopropane –
cosensitizer ,
Cossee’s mechanism
coulombic potential energy
Coulomb integral ,
Coulomb’s law
Coulson approach
– hydrogen molecule –
– hydrogenoid molecules, PMO theroy –
coumarin/polyene-type organic dyes
cross-conjugated dienones
crossed cycloadducts
crossed [?? +?? ]-cycloaddition
cross-enyne metathesis
cross-metathesis, of -hexyne with nitriles
(±)-crotepoxide
crotyl double bond
crowded silylenes
crystalline spirophosphorane
cubane ,
Cu(I)-catalyzed azide/alkyne cyclocondensation
(CuAAC)
Cu-catalyzed Mirozoki–Heck coupling
CuCl
reoxidizing agent
Curtin–Hammett principle – ,
C
v symmetrical cyclic four-electron transition structure

-cyanoanthracene
cyanobenzoate (S) ,
-cyano- , -diphenylcyclopropylithium
-cyano- -methylquinolium perchlorate
-cyanonaphthalene
cyclic ??-diazoketones
cyclic ??-conjugation
cyclic product
cycloaddents , – ,
– , –
, , – ,
, , , , ,
cycloaddition , ,
, -cycloaddition Index
( + )-cycloaddition –
( + )-cycloaddition ,
, – , – ,
–

– of singlet oxygen
( + + )-cycloaddition , , , –
( + + )-cycloaddition , –
( + + + )-cycloaddition –
( + )-cycloaddition –
( + )-cycloaddition – , –
, , –
( + + )-cycloaddition ,
( + )-cycloaddition , –
( + )-cycloaddition –
( + )-cycloaddition ,
,
( + + )-cycloaddition ,
( + )-cycloaddition –
( + )-cycloaddition ,
( + )-cycloaddition , –
( + + )-cycloaddition
( + )-cycloaddition ,
( + )-cycloaddition , , ,
( + )-cycloaddition
(m+n)-cycloaddition –
(n+ )-cycloaddition
cycloadditions and cycloreversions
– allene cycloaddition –
– aromaticity –
– cheletropic elimination
– concerted Diels–Alder reactions –
– (m+n)-cycloadditions –
– , -dipolar –
– diradicaloid model –
– , -diradical/zwitterion intermediates or diradicaloid
transition structures –
– hetero-Diels–Alder reactions –
– ketenes and keteniminium salts –
– Longuet–Higgins model –
– noncatalyzed ( + )- and ( + )-cycloadditions
–
– olefinations analogous to Wittig reaction –
– ??-facial selectivity of Diels–Alder reactions –
– regioselectivity of Diels–Alder reactions –
– sharpless asymmetric dihydroxylation of alkenes
–
– stereoselectivity of Diels–Alder reactions –
– structural effects on the Diels–Alder reactivity
–
– thermal ( + + )-cycloadditions –
– thermal higher order (m+n)-cycloadditions –
– Wittig olefination –
– Woodward–Hoffmann rules –
cycloadduct
, -cycloadducts
( + )-cycloadducts
( + )-cycloadducts ,
( + )-cycloadducts
cycloalkenes, ring strain
cyclobutadiene
– antiaromatic destabilization energy ,
– argon matrix isolation of
– four ??-MOs of
– gas-phase standard heat formation of ,
– geometries of –
– hemicarcerand ,
– Pettit’s experiments
– photochemical generation of
– PMO diagram
– proton affinity of
– structure of
– total ?? energy of
cyclobuta- , -dione ,
cyclobutane , , , –
–
,
cyclobutane pyrimidine dimers
cyclobutanone , , , –
cyclobutene , , , , – ,
, – ,
cyclobutene- , -diyl dication ,
cyclobutenyl zwitterion
cyclobutyleniminium adduct
cyclodecane
cyclodimerization – ,
–
, , , ,
cycloheptadecane
cycloheptane
cycloheptatriene ,
cyclohepta- , , -trien- -one
cycloheptatrienyl cation ,
cyclohexa- , - and , -dienones
cyclohexa- , -diene ,
,

cyclohexa- , -diene ,
cyclohexadienyl anion ,
cyclohexadienyl cation , ,
cyclohexadienyl radical ,
cyclohexadienone ,
cyclohexa- , -dienones
cyclohexa- , -dienones ,
cyclohexadienyl anion ,
cyclohexane
– chair ? chair interconversion
– monosubstituted cyclohexanes Index
– planar cyclohexane
– twist-boat conformer
cyclohexanecarbonitrile
cyclohexane- , -dione
cyclohexanol
cyclohexanones , , – ,
cyclohexene , , – ,
,
, , ,

– Pd(II)-catalyzed allylic acetoxylation of
cyclononane ,
cyclononyne
cycloocta- , -diene
cycloocta- , -diene ,

cyclooctane ,
cyclooctatetraene , – ,
, ,
cycloocta- , , -trienes ,
cyclooct- -enol
cyclopentadiene
– – ,
, – , ,
cyclopentadienones
cyclopentadienyl anion – , –
cyclopentadienylcarbene
cyclopentadienylmethyl radical
cyclopentadienyl systems
cyclopentane , , , – ,
,
cyclopentanone , , ,
cyclopentene , , ,
, , ,
cyclopent- -ene- , -dione
cyclopent- -enone
cyclopent- -enone ,
cyclopent- -en- -yl and cyclohex- -en- -yl cation
cyclopentenyl cation intermediate
([(cyclopent- -en- -yl)- -yl]methyl diradical)
cyclopentylethyne
cyclopropanation by ( + )-cheletropic reaction of
carbenes –
cyclopropane , , , , , ,
cyclopropene , , ,
,
cyclopropene- -carbaldehyde ,
cyclopropenyl systems
-cyclopropyl- -alkyl radicals
cyclopropyl cations , ,
-cyclopropyl- , -dienes
cyclopropylmethyl cation , ,
cyclopropylmethyl/homoallyl radical rearrangement
,
cyclopropylmethyl radical ,
cyclopropyl vs. cyclobutyl substituent effect –
cyclotetradecane
cyclotrimerization of t-butylfluroroacetylene
cylohexene derivatives
cytochrome P – ,

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كتاب Organic Chemistry - Theory, Reactivity and Mechanisms in Modern Synthesis 761752

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