Stereochemistry of organic compounds

Description

Stereochemistry of Organic Compounds The first fully referenced, comprehensive book on this subject in more than thirty years, Stereochemistry of Organic Compounds contains up-to-date coverage and insightful exposition of all important new concepts, developments, and tools in the rapidly advancing field of stereochemistry, including: * Asymmetric and diastereoselective synthesis * Conformational analysis * Properties of enantiomers and racemates * Separation and analysis of enantiomers and diastereoisomers * Developments in spectroscopy (including NMR), chromatography, and molecular mechanics as applied to stereochemistry * Prostereoisomerism * Conceptual foundations of stereochemistry, including terminology and symmetry concepts * Chiroptical properties Written by the leading authorities in the field, the text includes more than 4,000 references, 1,000 illustrations, and a glossary of stereochemical terms. Contents 1. INTRODUCTION 1.1. Scope 1.2. History 1.3. Polarimetry and Optical Rotation References 2. STRUCTURE 2.1. Meaning, Factorization, Internal Coordinates.Isomers 2.2. Constitution 2.3. Configuration 2.4. Conformation 2.5. Determination of Structure 2.6. A Priori Calculation of Structure 2.7. Molecular Models References 3. STEREOISOMERS 3.1. Nature of Stereoisomers 3.2. Enantiomers 3.3. Diastereomers References 4. SYMMETRY 4.1. Introduction 4.2. Symmetry Elements 4.3. Symmetry Operators. Symmetry Point Groups 4.4. Desymmetrization 4.5. Averaged Symmetry 4.6. Symmetry and Molecular Properties References 5. CONFIGURATION 5.1. Definitions: Relative and Absolute Configuration 5.2. Absolute Configuration and Notation 5.3. Determination of Absolute Configuration 5.4. Relative Configuration and Notation 5.5. Determination of Relative Configuration of SaturatedAliphatic Compounds 5.6. Conclusion: Network Arguments References 6. PROPERTIES OF STEREOISOMERS. STEREOISOMERDlSCRlMl NATION 6.1. Introduction 6.2. Stereoisomer Discrimination 6.3. The Nature of Racemates 6.4. Properties of Racemates and of Their EnantiomerComponents 6.5. Determination of Enantiomer and DiastereomerComposition References 7. SEPARATION OF STEREOISOMERS. RESOLUTION.RACEMIZATION 7.1. Introduction 7.2. Separation of Enantiomers by Crystallization 7.3. Chemical Separation of Enantiomers viaDiastereomers 7.4. Enantiomeric Enrichment. Resolution Strategy 7.5. Large Scale Resolution 7.6. Kinetic Resolution 7.7. Miscellaneous Separation Methods 7.8. Racemization References 8. HETEROTOPIC LIGANDS AND FACES(PROSTEREOISOMERISM, PROCH IRALITY) 8.1. Introduction. Terminology 8.2. Significance. History 8.3. Homotopic and Heterotopic Ligands and Faces 8.4. Heterotopicity and Nuclear Magnetic Resonance 8.5. Heterotopic Ligands and Faces in Enzyme-CatalyzedReactions 8.6. Pro2-ChiraCl enters: Chiral Methyl, Phosphate, andSulfate Groups References 9. STEREOCHEMISTRY OF ALKENES 9.1. Structure of Alkenes. Nature of cis-transIsomerism 9.2. Determination of Configuration of cis-trans Isomers 9.3. Interconversion of cis-trans Isomers: Position ofEquilibrium and Methods of Isomerization References 10. CONFORMATION OF ACYCLIC MOLECULES 10.1. Conformation of Ethane, Butane, and Other SimpleSaturated Acyclic Molecules 10.2. Conformation of Unsaturated Acyclic andMiscellaneous Compounds 10.3. Diastereomer Equilibria in Acyclic Systems 10.4. Physical and Spectral Properties of Diastereomers andConformers 10.5. Conformation and Reactivity: The Winstein-HolnessEquation and the Curtin-Hammett Principle References 11. CONFIGURATION AND CONFORMATION OF CYCLICMOLECULES 11.1. Stereoisomerism and Configurational Nomenclature ofRing Compounds 11.2. Determination of Configuration of Substituted RingCompounds 11.3. Stability of Cyclic Molecules 11.4. Conformational Aspects of the Chemistry of Six-Membered Ring Compounds 11.5. Chemistry of Ring Compounds Other Than Six-Membered Ones 11.6. Stereochemistry of Fused, Bridged, and Caged RingSystems References 12. STEREOSELECTIVE SYNTHESIS 12.1. Introduction 12.2. Diastereoselective Synthesis of AchiralCompounds 12.3. Diastereoselective Synthesis 12.4. Enantioselective Syntheses 12.5. Double Stereodifferentiation 12.6. Conclusion References 13. CHIROPTICAL PROPERTIES 13.1. Introduction 13.2. Optical Activity. Anisotropic Refraction 13.3. Circular Dichroism. Anisotropic Absorption 13.4. Applications of Optical Rotary Dispersion and CircularDichroism 13.5. Applications of Optical Activity 13.6. Vibrational Optical Activity 13.7. Circular Polarization of Emission. AnisotropicEmission References 14. CHIRALITY IN MOLECULES DEVOID OF CHIRAL CENTERS 14.1. Introduction. Nomenclature 14.2. Allenes 14.3. Alkylidenecycloalkanes 14.4. Spiranes 14.5. Biphenyls. Atropisomerism 14.6. Molecular Propellers and Gears 14.7. Helicenes 14.8. Molecules with Planar Chirality 14.9. Cyclostereoisomerism References GLOSSARY INDEX