Basic organic stereochemistry

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Basic organic stereochemistry / Ernest L. Eliel, Samuel H. Wilen, Michael P. Doyle

資料種別:

図書

出版情報:

New York : John Wiley & Sons, c2001

形態:

xiv, 688 p. ; 24 cm

著者名:

ISBN:

9780471374992 [0471374997]

書誌ID:

BA52671567

子書誌情報

フルテキスト

所蔵情報

他の版・巻

書誌詳細

注記:

Includes bibliographical references and index

主題:

異性体．立体化学．共鳴

言語:

英語

目次情報:

Preface

Introduction / 1：

Scope / 1-1.：

History / 1-2.：

Polarimetry and Optical Rotation / 1-3.：

References

Structure / 2：

Meaning, Factorization, Internal Coordinates, Isomers / 2-1.：

Constitution / 2-2.：

Configuration / 2-3.：

Conformation / 2-4.：

Determination of Structure / 2-5.：

A Priori Calculation of Structure / 2-6.：

Molecular Models / 2-7.：

Stereoisomers / 3：

Nature of Stereoisomers / 3-1.：

General / a.：

Barriers Between Stereoisomers and Residual Stereoisomers / b.：

Enantiomers / 3-2.：

Diastereomers / 3-3.：

General Cases

Degenerate Cases

Symmetry / 4：

Symmetry Elements / 4-1.：

Symmetry Operators and Symmetry Point Groups / 4-3.：

Point Groups Containing Chiral Molecules

Point Groups Containing Only Achiral Molecules

Averaged Symmetry / 4-4.：

Symmetry and Molecular Properties / 4-5.：

Rotation of Polarized Light

Dipole Moment

Symmetry Number / c.：

Definitions: Relative and Absolute Configuration / 5：

Absolute Configuration and Notation / 5-2.：

Determination of Absolute Configuration / 5-3.：

Bijvoet Method

Theoretical Approaches

Modification of Crystal Morphology in the Presence of Additives

Relative Configuration and Notation / 5-4.：

Determination of Relative Configuration of Saturated Aliphatic Compounds / 5-5.：

X-Ray Structure Analysis

Chemical Interconversion Not Affecting Bonds to the Stereogenic Atom

Methods Based on Symmetry Considerations

Correlation Via Compounds with Chiral Centers of Two Types / d.：

The Method of Quasi-Racemates / e.：

Chemical Correlations Affecting Bonds to a Chiral Atom in a "Known" Way (For an overview, see ref. 32.) / f.：

Correlation by Stereoselective Synthesis of "Known" Stereochemical Course / g.：

Chiroptical, Spectroscopic, and Other Physical Methods / h.：

Conclusion: Network Arguments / 5-6.：

Properties of Stereoisomers and Stereoisomer Discrimination / 6：

Stereoisomer Discrimination / 6-1.：

The Nature of Racemates / 6-3.：

Properties of Racemates and of Their Enantiomer Components / 6-4.：

Optical Activity

Crystal Shape

Density and Racemate Type

Melting Point

Solubility

Vapor Pressure

Infrared Spectra

Electronic Spectra / i.：

Nuclear Magnetic Resonance Spectra / j.：

X-Ray Spectra / k.：

Liquid State and Interfacial Properties / l.：

Chromatography / m.：

Mass Spectrometry / n.：

Interaction with Other Chiral Substances / o.：

Biological Properties / p.：

Origins of Enantiomeric Homogeneity in Nature / q.：

Determination of Enantiomer and Diastereomer Composition / 6-5.：

Chiroptical Methods

NMR Methods Based on Diastereotopicity

Chromatographic and Related Separation Methods Based on Diastereomeric Interactions

Kinetic Methods

Miscellaneous Methods

Separation of Stereoisomers, Resolution, and Racemization / 7：

Separation of Enantiomers by Crystallization / 7-1.：

Crystal Picking and Triage

Conglomerates

Preferential Crystallization

Asymmetric Transformation of Racemates and Total Spontaneous Resolution

Chemical Separation of Enantiomers via Diastereomers / 7-3.：

Formation and Separation of Diastereomers; Resolving Agents

Resolution Principles and Practice

Separation Via Complexes and Inclusion Compounds

Chromatographic Resolution

Asymmetric Transformations of Diastereomers

General Methods for the Separation of Diastereomers

Enantiomeric Enrichment and Resolution Strategy / 7-4.：

Kinetic Resolution / 7-5.：

Theory and Stoichiometric and Abiotic Catalytic Kinetic Resolution

Enzymatic Resolution

Miscellaneous Separation Methods / 7-6.：

Racemization / 7-7.：

Racemization Processes

Racemization of Amino Acids

Heterotopic Ligands and Faces: Prostereoisomerism and Prochirality / 8：

Introduction and Terminology / 8-1.：

Significance and History / 8-2.：

Homotopic and Heterotopic Ligands and Faces / 8-3.：

Homotopic Ligands and Faces

Enantiotopic Ligands and Faces

Diastereotopic Ligands and Faces

Concepts and Nomenclature

Heterotopicity and Nuclear Magnetic Resonance / 8-4.：

General Principles. Anisochrony

NMR in Assignment of Configuration and of Descriptors of Prostereoisomerism

Origin of Anisochrony

Conformationally Mobile Systems

Heterotopic Ligands and Faces in Enzyme-Catalyzed Reactions / 8-5.：

Heterotopicity and Stereoelective Synthesis

Heterotopicity and Enzyme-Catalyzed Reactions

Stereochemistry of Alkenes / 9：

Structure of Alkenes and Nature of cis-trans Isomerism / 9-1.：

Nomenclature

Cumulenes

Alkenes with Low Rotational Barriers and Nonplanar Alkenes

The C=N and N=N Double Bonds

Determination of Configuration of cis-trans Isomers / 9-2.：

Chemical Methods

Physical Methods

Interconversion of cis-trans Isomers: Position of Equilibrium and Methods of Isomerization / 9-3.：

Position of cis-trans Equilibria

Methods of Equilibration

Directed cis-trans Interconversion

Conformation of Acyclic Molecules / 10：

Conformation of Ethane, Butane, and Other Simple Saturated Acyclic Molecules / 10-1.：

Alkanes

Saturated Acyclic Molecules with Polar Substituents or Chains and the Anomeric Effect

Conformation of Unsaturated Acyclic and Miscellaneous Compounds / 10-2.：

Unsaturated Acyclic Compounds

Alkylbenzenes

Miscellaneous Compounds

Physical and Spectral Properties of Diastereomers and Conformers / 10-3.：

Dipole Moments

NMR Spectroscopy

Conformation and Reactivity: The Winstein-Holness Equation and the Curtin-Hammett Principle / 10-4.：

Configuration and Conformation of Cyclic Molecules / 11：

Stereoisomerism and Configurational Nomenclature of Ring Compounds / 11-1.：

Determination of Configuration of Substituted Ring Compounds / 11-2.：

Symmetry-Based Methods

Methods Based on Physical and Chemical Properties

Correlation Methods

Stability of Cyclic Molecules / 11-3.：

Strain

Ease of Cyclization as a Function of Ring Size

Ease of Ring Closure as a Function of the Ring Atoms and Substitutents: The Thorpe-Ingold Effect

Baldwin's Rules

Conformational Aspects of the Chemistry of Six-Membered Ring Compounds / 11-4.：

Cyclohexane

Monosubstituted Cyclohexanes

Disubstituted and Polysubstituted Cyclohexanes

Conformation and Physical Properties in Cyclohexane Derivatives

Conformation and Reactivity in Cyclohexanes

sp[superscript 2] Hybridized Cyclohexyl Systems

Six-Membered Saturated Heterocycles

Chemistry of Ring Compounds Other than Six-Membered Ones / 11-5.：

Three-Membered Rings

Four-Membered Rings

Five-Membered Rings

Rings Larger Than Six-Membered

Stereochemistry of Fused, Bridged, and Caged Ring Systems / 11-6.：

Fused Rings

Bridged Rings

Propellanes

Catenanes, Rotaxanes, Knots, and Mobius Strips

Cubane, Tetrahedrane, Dodecahedrane, Adamantane, and Buckminsterfullerene

Chiroptical Properties / 12：

Optical Activity and Anisotropic Refraction / 12-1.：

Origin and Theory

Optical Rotatory Dispersion

Circular Dichroism and Anisotropic Absorption / 12-3.：

Applications of Optical Rotary Dispersion and Circular Dichroism / 12-4.：

Determination of Configuration and Conformation: Theory

Classification of Chromophores

Sector and Helicity Rules

Exciton Chirality

Other Applications: Induced ORD and CD

Circular Dichroism of Chiral Polymers

Applications of Optical Activity / 12-5.：

Polarimetry

Empirical Rules and Correlations: Calculation of Optical Rotation

Vibrational Optical Activity / 12-6.：

Chirality in Molecules Devoid of Chiral Centers / 13：

Introduction and Nomenclature / 13-1.：

Allenes / 13-2.：

Historical Overview and Natural Occurrence

Synthesis of Optically Active Allenes

Determination of Configuration and Enantiomeric Purity of Allenes

Cyclic Allenes, Cumulenes, and Ketene Imines

Alkylidenecycloalkanes / 13.3.：

Spiranes / 13-4.：

Biphenyls and Atropisomerism / 13-5.：

Biphenyls and Other Atropisomers of the sp[superscript 2]-sp[superscript 2] Single-Bond Type

Atropisomerism About sp[superscript 2]-sp[superscript 3] Single Bonds

Atropisomerism About sp[superscript 3]-sp[superscript 3] Bonds

Molecular Propellers / 13-6.：

Helicenes / 13-7.：

Molecules with Planar Chirality / 13-8.：

Cyclophanes

trans-Cycloalkenes

Metallocenes and Related Compounds

Index

Preface

Introduction / 1：

Scope / 1-1.：

History / 1-2.：

Polarimetry and Optical Rotation / 1-3.：

References

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