Reactive intermediates in organic chemistry: structure, mechanism, and reactions
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| Main Author: | |
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| Format: | Book |
| Language: | English |
| Published: |
Weinheim
Wiley-VCH
2014
|
| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Physical Description: | X, 283 S. Ill., graph. Darst. |
| ISBN: | 3527335943 9783527335947 9783527678259 |
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Record in the Search Index
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CONTENTS
PREFACE
IX
1 INTRODUCTION 1
1.1 REACTION MECHANISM AND REACTION ARROWS 4
1.2 PROPERTIES AND CHARACTERISTICS OF A REACTION 5
1.2.1 REACTANTS AND REAGENTS 6
1.2.2 PRODUCT SELECTIVITY 6
1.2.3 REACTION CHARACTERISTICS 7
1.2.4 FACTORS THAT INFLUENCE REACTIONS 7
1.3 SUMMARY 16
FURTHER READING 19
2 CARBOCATIONS 21
2.1 INTRODUCTION 21
2.2 HISTORY 22
2.2.1 CARBONIUM IONS AND CARBENIUM IONS 23
2.3 STRUCTURES AND GEOMETRY OF CARBOCATIONS 26
2.4 GENERATION OF CARBOCATION 28
2.4.1 FROM A HALIDE 29
2.4.2 FROM AN ALCOHOL 29
2.4.3 FROM AN AMINE 29
2.4.4 FROM AN ALKENE 30
2.4.5 FROM CARBONYL COMPOUNDS 30
2.4.6 SOLVENT EFFECTS 30
2.5 CARBOCATION STABILITY 31
2.6 DETECTION OF CARBOCATIONS 36
2.7 FATE OF CARBOCATIONS 37
2.7.1 REACTION WITH A NUCLEOPHILE 38
2.7.2 ELIMINATION OF A PROTON 38
2.7.3 REARRANGEMENTS OF CARBOCATIONS 39
2.7.4 CATIONIC POLYMERIZATION 50
2.8 NONDASSICAL CARBOCATIONS 51
2.9 RADICAL CATIONS 55
HTTP://D-NB.INFO/1038860903
VII
CONTENTS
2.10 SUMMARY 60
FURTHER READING 64
3 CARBANIONS 65
3.1 STRUCTURE AND GEOMETRY OF CARBANIONS 65
3.2 GENERATION OF CARBANIONS 69
3.2.1 REDUCTION OF C-X BOND WITH METAL 69
3.2.2 DEPROTONATION FROM A C-H BOND 70
3.2.3 REACTION OF A METAL WITH AN ALKENE 70
3.2.4 A NEGATIVE ION ADDS TO A CARBON-CARBON DOUBLE OR TRIPLE BOND 71
3.3 STABILITY OF CARBANIONS 72
3.4 REACTIONS OF CARBANIONS 77
3.5 ENOLATE REACTIONS WITH CARBONYL GROUPS 78
3.5.1 ALDOL CONDENSATION 78
3.5.2 ENAMINE ADDITIONS 81
3.5.3 ROBINSON RING-FORMING REACTION 81
3.6 REARRANGEMENTS OF CARBANIONS 86
3.6.1 HOMOALLYLIC REARRANGEMENTS 86
3.7 CHIRAL CARBANIONS 90
3.8 CARBANIONS AND TAUTOMERISM 91
3.8.1 MECHANISM OF KETO-ENOL INTERCONVERSION 91
3.9 SUMMARY 96
FURTHER READING 100
4 RADICALS 101
4.1 INTRODUCTION 101
4.2 DETECTION AND CHARACTERIZATION OF RADICALS 103
4.3 STRUCTURE AND BONDING OF RADICALS 107
4.4 GENERATION OF FREE RADICALS 111
4.5 STABILITY OF RADICALS 114
4.6 REACTIONS OF FREE RADICALS 316
4.7 STEREOCHEMISTRY OF RADICAL REACTIONS 131
4.7.1 CYDIZATION BY INTRAMOLECULAR ADDITION REACTIONS 136
4.8 BIRADICALS 142
4.9 SUMMARY 146
FURTHER READING 151
5 CARBENES 153
5.1 STRUCTURE AND GEOMETRY OF CARBENES 153
5.2 GENERATION OF CARBENES 160
5.2.1 THERMOLYSIS OR PHOTOLYSIS OF DIAZO COMPOUNDS 160
5.2.2 REACTION OF N-NITROSOUREAS WITH BASE 161
5.2.3 REACTION OF TOSYLHYDRAZONE WITH BASE 162
5.2.4 CARBENE FORMATION BY A-ELIMINATION 163
5.2.5 GENERATION OF CARBENOIDS (SIMMONS-SMITH REACTION) 165
CONTENTS
I VII
5.2.6 FORMATION OF CARBENES UNDER NEUTRAL CONDITIONS 165 \
5.2.7 GENERATION OF CARBENES FROM SMALL RINGS 166
5.3 REACTIONS OF CARBENES 167
5.3.1 ADDITION REACTIONS 168
5.3.2 CYCLOADDITION TO 1,2-DIENES (ALLENES) 176
5.3.3 CYCLOADDITION TO 1,3-DIENE 176
5.3.4 CYCLOADDITION TO ALKYNES 177
5.3.5 INSERTION REACTIONS 177
5.3.6 REARRANGEMENT OF CARBENES 181
5.3.6.1 WOLFF REARRANGEMENT 182
5.3.7 REACTIONS OF CARBENES WITH NUCLEOPHILES 187
5.4 CARBENES AND CARBENE LIGANDS IN ORGANOMETALLIC CHEMISTRY 188
5.5 SUMMARY 192
FURTHER READING 195
6 NITRENES 197
6.1 INTRODUCTION 197
6.2 * STRUCTURE AND REACTIVITY 198
6.3 GENERATION OF NITRENES 202
6.3.1 AZIDES 203
6.3.2 ISOCYANATES 205
6.3.3 YLIDES 205
6.3.4 SMALL RINGS 206
6.3.5 HETEROCYCLES 206
6.3.6 A-ELIMINATION 207
6.3.7 REDUCTION OF NITRO AND NITROSO COMPOUNDS 207
6.3.8 OXIDATION OF AMINES 208
6.3.9 FROM SULFINYLAMINES 208
6.4 REACTIONS OF NITRENES 209
6.4.1 CYCLOADDITION REACTIONS OF NITRENES 209
6.4.1.1 CYCLOADDITION TO ALKENES 209
6.4.1.2 CYCLOADDITION TO 1,3-DIENES 210
6.4.1.3 CYCLOADDITION TO ALKYNES 211
6.4.1.4 CYCLOADDITION TO ARENES 212
6.4.2 INSERTION REACTIONS OF NITRENES 212
6.4.3 REARRANGEMENT OF NITRENES 216
6.4.4 REACTIONS OF NITRENES WITH NUCLEOPHILES 218
6.5 SUMMARY 220
FURTHER READING 223
7 MISCELLANEOUS INTERMEDIATES 225
7.1 ARYNES 225
7.1.1 INTRODUCTION 225
7.1.2 STRUCTURE AND REACTIVITY 226
7.1.3 GENERATION OF ARYNES 230
VIII
|
CONTENTS
7.1.4 REACTIONS OF ARYNES 236
7.1.4.1 NUDEOPHILIC ADDITION TO ARYNES 237
7.1.4.2 REGIOCHEMISTRY OF THE TRIPLE BOND FORMATION 239
7.1.4.3 CYDOADDITION REACTIONS OF ARYNES (DIELS-ALDER REACTION) 240
7.1.4.4 1,3-DIPOLAR CYDOADDITION 243
7.1.5 USES OF ARYNES IN ORGANIC SYNTHESIS 245
7.2 KETENES AND CUMULENES 246
7.2.1 INTRODUCTION 246
7.2.2 GENERATION OF KETENES 248
7.2.3 PHOTOCHEMICAL GENERATION OF KETENES 250
7.2.4 REACTIONS OF KETENES 251
7.3 ORTHO-QUINONE METHIDES 253
7.4 ZWITTERIONS AND DIPOLES 258
7.5 ANTIAROMATIC SYSTEMS 262
7.6 TETRAHEDRAL INTERMEDIATES 264
7.6.1 ACETALS AND HEMIACETALS 267
7.6.2 WEINREB AMIDES 269
7.6.3 APPLICATIONS IN BIOMEDICINE 269
7.7 SUMMARY 270
FURTHER READING 273
INDEX 275 |
| any_adam_object | 1 |
| author | Singh, Maya Shankar |
| author_GND | (DE-588)1049137973 |
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| dewey-full | 547.2 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.2 |
| dewey-search | 547.2 |
| dewey-sort | 3547.2 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| format | Book |
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| spelling | Singh, Maya Shankar Verfasser (DE-588)1049137973 aut Reactive intermediates in organic chemistry structure, mechanism, and reactions Maya Shankar Singh Weinheim Wiley-VCH 2014 X, 283 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Tandem-Reaktion (DE-588)4306783-9 gnd rswk-swf Reaktive Zwischenstufe (DE-588)4177127-8 gnd rswk-swf Reaktive Zwischenstufe (DE-588)4177127-8 s Tandem-Reaktion (DE-588)4306783-9 s DE-604 Erscheint auch als Online-Ausgabe, EPUB 978-3-527-67827-3 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-67826-6 Erscheint auch als Online-Ausgabe, PDF 978-3-527-67828-0 X:MVB text/html http://deposit.dnb.de/cgi-bin/dokserv?id=4431085&prov=M&dok_var=1&dok_ext=htm Inhaltstext DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027178003&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Singh, Maya Shankar Reactive intermediates in organic chemistry structure, mechanism, and reactions Tandem-Reaktion (DE-588)4306783-9 gnd Reaktive Zwischenstufe (DE-588)4177127-8 gnd |
| subject_GND | (DE-588)4306783-9 (DE-588)4177127-8 |
| title | Reactive intermediates in organic chemistry structure, mechanism, and reactions |
| title_auth | Reactive intermediates in organic chemistry structure, mechanism, and reactions |
| title_exact_search | Reactive intermediates in organic chemistry structure, mechanism, and reactions |
| title_full | Reactive intermediates in organic chemistry structure, mechanism, and reactions Maya Shankar Singh |
| title_fullStr | Reactive intermediates in organic chemistry structure, mechanism, and reactions Maya Shankar Singh |
| title_full_unstemmed | Reactive intermediates in organic chemistry structure, mechanism, and reactions Maya Shankar Singh |
| title_short | Reactive intermediates in organic chemistry |
| title_sort | reactive intermediates in organic chemistry structure mechanism and reactions |
| title_sub | structure, mechanism, and reactions |
| topic | Tandem-Reaktion (DE-588)4306783-9 gnd Reaktive Zwischenstufe (DE-588)4177127-8 gnd |
| topic_facet | Tandem-Reaktion Reaktive Zwischenstufe |
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