Basic Organic Stereochemistry
BASIC ORGANIC STEREOCHEMISTRY ERNEST L. ELIEL SAMUEL H. WILEN MICHAEL P. DOYLE Preface xiii 1 Introduction 1 1-1. Scope, 1 1-2. History, 1 1-3. Polarimetry and Optical Rotation, 5 References, 7 2 Structure 8 2-1 . Meaning, Factorization, Internal Coordinates, Isomers, 8 2-2. Constitution, 1 1 2-3. Configuration, 1 3 2-4. Conformation, 1 5 2-5 . Determination of Structure, 1 7 2-6. A Priori Calculation of Structure, 20 2-7 . Molecular Models, 25 References, 26 3 Stereoisomers 30 3-1. Nature of Stereoisomers, 3 0 a. General, 30 b. Barriers Between Stereoisomers and Residual Stereoisomers, 3 4 3-2. Enantiomers, 3 6 3-3. Diastereomers, 3 9 a. General Cases, 39 b . Degenerate Cases, 42 References, 44 4 Symmetry 45 4-1 . Introduction, 4 5 4-2. Symmetry Elements, 45 4-3. Symmetry Operators and Symmetry Point Groups, 48 a. Point Groups Containing Chiral Molecules, 4 9 b. Point Groups Containing Only Achiral Molecules, 5 1 4-4. Averaged Symmetry, 5 8 4-5. Symmetry and Molecular Properties, 59 a. Rotation of Polarized Light, 5 9 b. Dipole Moment, 6 1 c. Symmetry Number, 6 2 References, 63 5 Configuration 65 5-1 . Definitions : Relative and Absolute Configuration, 6 5 5-2. Absolute Configuration and Notation, 67 5-3. Determination of Absolute Configuration, 7 5 a. Bijvoet Method, 75 b. Theoretical Approaches, 77 c. Modification of Crystal Morphology in the Presence of Additives, 7 7 5-4. Relative Configuration and Notation, 79 5-5. Determination of Relative Configuration of Saturated Aliphati c Compounds, 8 4 a.
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