Stereochemistry of carbon compounds:
Saved in:
| Main Author: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
New York [u.a.]
McGraw-Hill
1962
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| Series: | McGraw-Hill series in advanced chemistry
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| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XV, 486 S. graph. Darst. |
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Record in the Search Index
| _version_ | 1804122997428060160 |
|---|---|
| adam_text | STEREOCHEMISTRY OF
CARBON COMPOUNDS
ERNEST L ELIEL
Professor of Chemistry
University of Notre Dame
McGRAW-HILL BOOK COMPANY, INC 1962
New York San Francisco _ Toronto London
CONTENTS
Preface vii
Chapter 1 Introduction 1
1-1 Scope I
1-2 History 1
1-3 Optical and Geometrical Isomerism 4
General References 6
Chapter 2 Optical Isomerism 7
2-1 Polarimetry 7
2-2 Molecular Dissymmetry 9
2-3 Molecular Models 13
General References 15
Chapter 3 Optical Isomerism Due to Asymmetric Carbon Atoms 16
3-1 Compounds with One Asymmetric Carbon Atom 16
3-2 Compounds with Two or More Unequal Asymmetric Carbon Atoms 20
3-3 Compounds Containing Like Asymmetric Carbon Atoms 26
3-4 Compounds with Asymmetric Carbon Atoms in Branched Chains 29
General References 30
Chapter 4 Racemic Modifications 31
4-1 Nature of Racemic Modifications 31
4-2 Formation of Racemic Modifications 32
a By Mixing 32
b By Synthesis 32
c By Racemization 33
i Thermal Racemization 34
ii By Anion Formation 35
iii By Cation Formation 36
iv By Reversible Formation of Stable Inactive Intermediates 37
v By Walden Inversion 38
d By Chemical Transformation 38
i Epimerization 39
ii Mutarotation and Firs!-order Asymmetric Transformation 40
4-3 Properties of Racemic Modifications 43
a Racemic Mixtures 44
b Racemic Compounds 44
c Racemic Solid Solutions 45
xi
xii CONTENTS
4-4 Resolution of Racemic Modifications 47
a Resolution by Mechanical Separation of Crystals 47
b Resolution by Formation of Diastereoisomers Second-order Asym
metric Transformations 49
i Acids 52
ii Bases 52
iii Amino Acids 53
iv Alcohols 55
v Aldehydes and Ketones 56
vi Miscellaneous 57
Resolution via Molecular Complexes Resolution by Chromatog
raphy Other Methods of Physical Separation Second-order Asym
metric Transformation
c Resolution by Equilibrium Asymmetric Transformation 63
d Resolution by Kinetic Asymmetric Transformation 65
i Kinetic Method of Resolution 65
ii Asymmetric Synthesis 68
iii Asymmetric Destruction 74
e Biochemical Asymmetric Transformation • 75
f Absolute Asymmetric Synthesis 78
g Asymmetric Syntheses Involving Symmetric Compounds 81
4-5 Criteria of Optical Purity 83
General References 85
Chapter 5 Configuration 87
5-1 Definition 87
5-2 Notation 88
5-3 Absolute Configuration ~ 95
5-4 Relative Configuration 97
a Chemical Interconversion Not Affecting Bonds to the Asymmetric
Atom _ 97
b Chemical Correlation Involving Diastereoisomers 97
c The Method of Quasi-racemates 106
d The Method of Optical Comparison 110
e Configurational Assignment Based on Asymmetric Synthesis 114
f Chemical Transformation Involving the Asymmetric Center in a Pre
dictable Way 115*
i The Nucleophilic Displacement Reaction 117
ii Intramolecular Rearrangements at Saturated Carbons 119
5-5 Synthesis of Optically Active Compounds 120
General References 123
Chapter 6 Conformation and Reactivity in Acyclic Compounds 124
6-1 The Meaning of Conformation 124
6-2 Conformation and Physical Properties 126
a Dipole Moments 127
b Infrared and Raman Spectra 128
c Microwave Spectra 133
d Nuclear Magnetic Resonance Spectra 134
e X-ray and Electron Diffraction 136
6-3 Conformational Effects on Stability and Reactivity 137
a Differences in Stability of Diastereoisomers 138
CONTENTS xiii
b The Relative Reactivity of Diastereoisomers 139
i Ionic Elimination 140
ii Intramolecular Rearrangements 142
iii Neighboring-group Participation 146
iv Molecular Elimination 149
c The Relation of Conformation to Reactivity in Individual Compounds
The Curtin-Hammett Principle 149
6-4 Optical Isomerism Due to Restricted Rotation (Atropisomerism) 156
a Biphenyl Isomerism 156
b Isomerism in Polyphenyls 165
c The Configuration of Active Biphenyls 166
? d Other Types of Asymmetry Due to Restricted Rotation 173
^ e Effects of Atropisomerism on Physical Properties 177
General References 178
Chapter 7 Some Aspects of the Stereochemistry of Ring Systems 180
7-1 Stereoisomerism of Rings 180
a Number and Kind of Stereoisomers 180
b Determination of Configuration 183
7-2 Stability of Rings 188
a As a Function of Ring Size 188
b As a Function of the Nature of the Ring 190
c As a Function of Ring Substituents 196
7-3 Ease of Ring Formation 198
a As a Function of Ring Size 198
b As a Function of the Nature and Degree of Substitution of the Ring
Atoms 201
General References 202
Chapter 8 The Actual Shape of Six-membered Rings and Its Relation to Properties and
Reactivity 204
8-1 The Shape of Cyclohexane Rings - 204
8-2 Monosubstituted Cyclohexanes 208
8-3 Disubstituted Cyclohexanes 211
8-4 Physical Properties of Substituted Cyclohexanes 216
8-5 Conformation and Chemical Reactivity in Cyclohexane 219
8-6 Quantitative Treatment of Mobile Systems 234
8-7 Conformational Effects in Six-membered Rings Containing Unsaturation 239
8-8 Six-membered Heterocyclic Rings 246
General References 246
Chapter 9 The Shape of Rings Other Than Six-membered Ones 248
9-1 Five-membered Rings 248
9-2 Rings Larger Than Six-membered 252
9-3 Conformational Effects in Medium-sized Rings Transannular Effects 253
9-4 The Concept of I-Strain 265
General References 269
Chapter 10 Fused Rings and Bridged Rings 270
10-1 Scope 270
10-2 Fused Systems 270
a Bicyclic Systems 270
xiv CONTENTS
b Polycyclic Systems 281
10-3 Bridged Systems 294
a Occurrence and Availability 294
b Stereochemical Restrictions The Bredt Rule 298
c Some Further Reactions of the Norbornane System 302
General References 306
Chapter 11 The Stereoisomerism of Allenes and Related Compounds 307
11-1 Enantiomerism in Allenes, Alkylidenecycloalkanes, and Spiranes 307
11-2 Configurational Nomenclature 311
11-3 Correlation of Axial Dissymmetry and Centrodissymmetry 313
General References 317
Chapter 12 Geometrical Isomerism and the Stereochemistry of Olefins 318
12-1 Nature of Geometrical Isomerism 318
12-2 Determination of Configuration of Geometrical Isomers 321
12-3 Physical Properties of Geometrical Isomers 325
a Dipole Moments 325
b Melting Points, Boiling Points, Densities, and Refractive Indices 326
c Acid Strength 327
d Ultraviolet Spectra 329
e Infrared and Raman Spectra 333
f Nuclear Magnetic Resonance Spectra 335
g X-ray and Electron Diffraction 336
12-4 Relative Stability and Interconversion of Geometrical Isomers 337
a Relative Stability of cis-trans Isomers 337
b Interconversion of Geometrical Isomers 341
12-5 Stereochemistry of Addition Reactions of Acetylenes and Their Reversal 346
12-6 Stereochemistry of Addition Reactions of Olefins 349
a Hydrogenation 350
b Electrophilic Addition 355
c Molecular Addition * 357
d Free-radical Addition 361
e Addition of Carbenes and Methylenes 365
f Nucleophilic Addition 367
12-7 Stereochemistry of Nucleophilic Displacement in Olefinic Halides 368
General References 370
Chapter 13 The Stereochemistry of Tricovalent Carbon 372
13-1 Introduction 372
13-2 Carbonium Ions 372
13-3 Free Radicals 380
13-4 Carbanions 384
13-5 Stereochemistry of Hydrogenolysis 394
13-6 Stereochemistry of Radiolysis 395
General References 397
Chapter 14 Optical Rotation and Optical Rotatory Dispersion 398
14-1 Relation between Rotation and Configuration 398
a Atomic Asymmetry 401
b Conformational Asymmetry 403
c Saturated Cyclic Compounds 406
CONTENTS XV
d Endocyclic Olefins 409
e Conclusion 412
14-2 Optical Rotatory Dispersion 412
a Terminology 412
b Plain Curves 414
c Rotatory Dispersion of Ketones 416
i Structure 418
ii Configuration 420
iii Conformation 422
iv Unsaturated Ketones and Diketones 422
d The Axial Haloketone Rule 422
^ e The Octant Rule 427
i Configuration 429
ii Conformation 430
f Absolute Configuration 430
g Ketal Formation 432
h Other Chromophores 433
General References 433
Chapter 15 Stereoselective Synthesis and Stereoregulated Polymerization 434
15-1 Stereoselective Synthesis 434
15-2 Stereoregulated Polymerization 446
General References 453
Name Index 455
Subject Index 467
|
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| series2 | McGraw-Hill series in advanced chemistry |
| spelling | Eliel, Ernest Ludwig 1921- Verfasser (DE-588)119087901 aut Stereochemistry of carbon compounds Ernest L. Eliel New York [u.a.] McGraw-Hill 1962 XV, 486 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier McGraw-Hill series in advanced chemistry Carbone - Composés Carbone - Composés ram Chimie organique ram Composés organiques ram Stéréochimie Stéréochimie ram Organische Verbindungen (DE-588)4043816-8 gnd rswk-swf Konfiguration Chemie (DE-588)4129572-9 gnd rswk-swf Konformation (DE-588)4164965-5 gnd rswk-swf Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf Stereochemie (DE-588)4129569-9 gnd rswk-swf Kohlenstoffverbindungen (DE-588)4164566-2 gnd rswk-swf Isomerie (DE-588)4162527-4 gnd rswk-swf Organische Chemie (DE-588)4043793-0 gnd rswk-swf 1\p (DE-588)4151278-9 Einführung gnd-content Organische Verbindungen (DE-588)4043816-8 s DE-604 Asymmetrische Synthese (DE-588)4135603-2 s Isomerie (DE-588)4162527-4 s Konformation (DE-588)4164965-5 s Konfiguration Chemie (DE-588)4129572-9 s Stereochemie (DE-588)4129569-9 s Organische Chemie (DE-588)4043793-0 s 2\p DE-604 Kohlenstoffverbindungen (DE-588)4164566-2 s 3\p DE-604 HEBIS Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=005705587&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk 2\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk 3\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk |
| spellingShingle | Eliel, Ernest Ludwig 1921- Stereochemistry of carbon compounds Carbone - Composés Carbone - Composés ram Chimie organique ram Composés organiques ram Stéréochimie Stéréochimie ram Organische Verbindungen (DE-588)4043816-8 gnd Konfiguration Chemie (DE-588)4129572-9 gnd Konformation (DE-588)4164965-5 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd Stereochemie (DE-588)4129569-9 gnd Kohlenstoffverbindungen (DE-588)4164566-2 gnd Isomerie (DE-588)4162527-4 gnd Organische Chemie (DE-588)4043793-0 gnd |
| subject_GND | (DE-588)4043816-8 (DE-588)4129572-9 (DE-588)4164965-5 (DE-588)4135603-2 (DE-588)4129569-9 (DE-588)4164566-2 (DE-588)4162527-4 (DE-588)4043793-0 (DE-588)4151278-9 |
| title | Stereochemistry of carbon compounds |
| title_auth | Stereochemistry of carbon compounds |
| title_exact_search | Stereochemistry of carbon compounds |
| title_full | Stereochemistry of carbon compounds Ernest L. Eliel |
| title_fullStr | Stereochemistry of carbon compounds Ernest L. Eliel |
| title_full_unstemmed | Stereochemistry of carbon compounds Ernest L. Eliel |
| title_short | Stereochemistry of carbon compounds |
| title_sort | stereochemistry of carbon compounds |
| topic | Carbone - Composés Carbone - Composés ram Chimie organique ram Composés organiques ram Stéréochimie Stéréochimie ram Organische Verbindungen (DE-588)4043816-8 gnd Konfiguration Chemie (DE-588)4129572-9 gnd Konformation (DE-588)4164965-5 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd Stereochemie (DE-588)4129569-9 gnd Kohlenstoffverbindungen (DE-588)4164566-2 gnd Isomerie (DE-588)4162527-4 gnd Organische Chemie (DE-588)4043793-0 gnd |
| topic_facet | Carbone - Composés Chimie organique Composés organiques Stéréochimie Organische Verbindungen Konfiguration Chemie Konformation Asymmetrische Synthese Stereochemie Kohlenstoffverbindungen Isomerie Organische Chemie Einführung |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=005705587&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT elielernestludwig stereochemistryofcarboncompounds |