Stereo-differentiating reactions : the nature of asymmetric reactions
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Bibliographic Information
Stereo-differentiating reactions : the nature of asymmetric reactions
Kodansha , Academic Press, c1977
- Other Title
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Rittai kubetsu hannō
- Uniform Title
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Rittai kubetsu hannō
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Translation of Rittai kubetsu hannō
Includes bibliographical references and indexes
Description and Table of Contents
Description
Stereo-Differentiating Reactions: The Nature of Asymmetric Reactions provides an introduction to asymmetric reactions. It brings together synthetic organic chemistry, stereochemistry, group theory, the theory of optical rotation, experimental methods, etc., all of which are basic to the study of stereo-differentiating reactions, to form a unified approach based on the new concept of "differentiation." The authors hope that the value of the new concept, which is rather more complex than conventional treatments of asymmetric reactions, will become clear in the present book. This new concept should be useful in many fields of study, not only the development of stereo-differentiating reactions, but also in the study of general reaction mechanisms in organic chemistry. The book contains nine chapters and begins with a historical background of studies on asymmetric reactions. This is followed by separate chapters on molecular symmetry and chirality; nomenclature for chirality, prochirality, and stereo-differentiating reactions; the mechanisms of stereo-differentiating reactions; methods for studying stereo-differentiating reactions; and the basic principle of optical activity.
Table of Contents
- PrefaceChapter 1 Historical BackgroundChapter 2 Molecular Symmetry and Chirality 2.1 Stereoisomerism 2.1.1 Classification According to Internal Energy 2.1.2 Classification According to Molecular Symmetry 2.2 Molecular Symmetry and Chirality 2.2.1 Method of Classification 2.2.2 Characteristics of Chiral Molecules and Counting Stereoisomers 2.2.3 Description of Isomers by Permutational Operations Appendix A Set and Group Appendix ? Symmetry Permutational Groups Appendix C Polya's ProcedureChapter 3 Nomenclature for Chirality and Prochirality 3.1 Nomenclature for Chiral Molecules 3.1.1 Nomenclature for Using the R, S System 3.1.2 Nomenclature for Conformational Isomers 3.2 Prochirality 3.2.1 Enantiotopic Relationships 3.2.2 Diastereotopic Relationships 3.2.3 Nomenclature for ProchiralityChapter 4 Nomenclature for Stereo-Differentiating Reactions 4.1 Fundamentals 4.2 Definition of Stereo-Differentiating Reactions 4.2.1 Reaction Character and Stereo-Differentiation 4.2.2 Historical Definitions of Asymmetric Reactions 4.2.3 New Definition and Classification for Reactions of Related Asymmetric Reactions 4.3 General Discussion on Stereo-Differentiating Reactions 4.3.1 Enantio-Differentiating Reactions 4.3.2 Diastereo-Differentiating ReactionsChapter 5 Stereo-Differentiating Reactions 5.1 Enantio-Differentiating Reactions 5.1.1 Enantioface-Differentiating Reactions 5.1.2 Enantiotopos-Differentiating Reactions 5.1.3 Enantiomer-Differentiating Reactions 5.2 Diastereo-Differentiating Reactions 5.2.1 Factors Affecting the Efficiency of Diastereo-Differentiation 5.2.2 Diastereoface-Differentiating Reactions 5.2.3 Diastereotopos-Differentiating Reactions 5.2.4 Intramolecular Diastereoface- and Diastereotopos-Differentiating Reactions 5.3 Special Stereo-Differentiating ReactionsChapter 6 Miscellaneous Stereo-Differentiating Reactions Systems 6.1 Stereo-Differentiating Reactions in Polymerization 6.1.1 Relationships of Stereo-Differentiation and Stereoregulation in Polymer Synthesis 6.1.2 The Stereo-Differentiating Process in Polymerization 6.2 Stereo-Differentiation in Enzyme Reactions 6.2.1 Aconitase 6.2.2 Alcohol Dehydrogenase 6.2.3 Enantiomer-Differentiating Reactions 6.3 So-called Absolute Asymmetric Synthesis 6.3.1 Configurational Enantiomer-Differentiating Reactions 6.3.2 Conformational Enantiomer-Differentiating Reactions 6.3.3 Enantioface-Differentiating Reactions 6.4 Enantio-Differentiating RacemizationsChapter 7 Mechanisms of Stereo-Differentiating Reactions 7.1 The Kinetic Approach 7.2 The Use of Stereochemical Models 7.2.1 Empirical Stereochemical Models (Experimental Rules for Stereo-Differentiating Reactions) 7.2.2 Mathematical Formulation of Stereo-Differentiating Reactions 7.3 Illustration Based on the New Concept of "Differentiation"Chapter 8 Methods for the Study of Stereo-Differentiating Reactions 8.1 Requirements for Experimental Condition for Stereo-Differentiating Reactions 8.1.1 Substrate 8.1.2 Reagent and Catalyst 8.1.3 Reaction Conditions and Subsequent Isolation and Purification of the Reaction Products 8.1.4 Confirmation of the Experimental Accuracy 8.1.5 Confirmation of Stereo-Differentiation 8.2 Evaluation of Stereo-Differentiating Ability 8.2.1 Stereo-Differentiating Ability and the Degree of Differentiation 8.2.2 Terms Expressing the Proportion of Stereoisomers 8.2.3 Determination of the Proportion of Stereoisomers 8.2.4 Relationship Between the Ratio of Stereoisomers Produced and Degree of Stereo-Differentiation 8.2.5 Distinction Between Enantio-Differentiation and Diastereo-Differentiation 8.2.6 Evaluation of the Degree of Stereo-Differentiation in Reactions Producing Optically Unstable ProductsChapter 9 Basic Principle of Optical Activity 9.1 Optical Rotation and the Properties of Light 9.1.1 The Wave Theory of Light 9.1.2 Refraction and Reflection of Light 9.1.3 Double Refraction 9.1.4 Equipment Used to Generate Polarized Light 9.1.5 Linearly Polarized Light and Circular Polarization 9.1.6 The Phenomenon of Optical Rotation 9.1.7 Circular Dichroism 9.2 Theory of Optical Rotation 9.2.1 The Spiral Model (Classical Theory) 9.2.2 Quantum Mechanical Treatment 9.3 Molecular Symmetry and Optical Activity 9.3.1 Symmetry Operations and Conservation of Scalars 9.3.2 Transformation of Eigenfunctions by Symmetry Operations 9.3.3 Transformation of Operators by Symmetry Operations 9.3.4 Transformation of D and ? by Symmetry Operations Appendix A Maxwell's Equations for a Plane Wave Appendix ? Relationship between Incident and Reflected Light Appendix C Fresnel's Equations Appendix D The Spiral Model
- Electric Moment Induced by an Alternating Magnetic Field Appendix ? The spiral Model: Magnetic Moment Induced by an Alternating Electric Field Appendix F Derivation of Eqs. 9.45 and 9.46 Appendix G Derivation of Eq. 9.53 Appendix ? Perturbed Wave Equation Appendix I Vector Treatment of Electromagnetic Waves Appendix J Derivation of Eq. 9.85 Appendix ? Derivation of Eqs. 9.89 and 9.90 Appendix L Derivation of Eq. 9.92 Appendix ? Derivation of Eq. 9.94 Appendix ? Value of Re{c*m(t)Cm(t)}rl (Eq. 9.103)Author IndexSubject Index
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