Stereo-Differentiating reactions - 1st Edition - ISBN: 9780123778505, 9780323155038

Stereo-Differentiating reactions

1st Edition

The nature of asymmetric reactions

Authors: Yoshiharu Izumi
eBook ISBN: 9780323155038
Imprint: Academic Press
Published Date: 1st January 1977
Page Count: 344
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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


Chapter 1 Historical Background

Chapter 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 Β Symmetry Permutational Groups

Appendix C Polya's Procedure

Chapter 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 Prochirality

Chapter 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 Reactions

Chapter 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 Reactions

Chapter 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 Racemizations

Chapter 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 Products

Chapter 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 Μ by Symmetry Operations

Appendix A Maxwell's Equations for a Plane Wave

Appendix Β 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 Ε 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 Η Perturbed Wave Equation

Appendix I Vector Treatment of Electromagnetic Waves

Appendix J Derivation of Eq. 9.85

Appendix Κ Derivation of Eqs. 9.89 and 9.90

Appendix L Derivation of Eq. 9.92

Appendix Μ Derivation of Eq. 9.94

Appendix Ν Value of Re{c*m(t)Cm(t)}rl (Eq. 9.103)

Author Index

Subject Index


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© Academic Press 1977
Academic Press
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Yoshiharu Izumi

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