Organozinc reagents in organic synthesis:
Saved in:
| Main Author: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Boca Raton [u.a.]
CRC Press
1996
|
| Series: | New directions in organic and biological chemistry
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | 411 S. |
| ISBN: | 0849391512 |
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| 245 | 1 | 0 | |a Organozinc reagents in organic synthesis |c Ender Erdik |
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| 650 | 7 | |a Zinc - Composés organiques |2 ram | |
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Record in the Search Index
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| adam_text | Contents
Chapter 1
Structure and Reactivity of Organozinc Reagents
1 1 Historical Background and Literature of Organozinc Chemistry 1
1 2 Structure of Organozinc Reagents 3
121 Ordinary Organozinc Reagents 4
122 2-Halozinciocarbonyl Compounds 6
123 Zinc Carbenoids 9
1 3 Reactivity of Organozinc Reagents 10
Chapter 2
Preparation of Organozinc Reagents
2 1 Preparation of Active Zinc Metal 18
211 Methods of Activating Commercial Zinc 19
2111 Chemical Activation of Zinc 19
2112 Ultrasonic Activation of Zinc 21
2113 Zinc Vapor Techniques 21
2114 Electrochemical Activation of Zinc 21
212 Methods of Preparing Reactive Zinc (Rieke Zinc) 22
2 2 Preparation of Ordinary Organozinc Reagents 23
221 Preparation of Ordinary Organozinc Reagents by
Oxidative Zincation 23
2211 Preparation of Alkylzinc Reagents by
Oxidative Zincation 23
2212 Preparation of Allylic, Benzylic, and Propargylic
Zinc Reagents by Oxidative Zincation 28
2213 Preparation of Alkenyl, Aryl, and Alkynyl Zinc
Reagents by Oxidative Zincation 35
222 Preparation of Ordinary Organozinc Reagents by
Halogen-Zinc Exchange 39
223 Preparation of Ordinary Organozinc Reagents by
Hydrogen-Zinc Exchange 44
224 Preparation of Ordinary Organozinc Reagents by
Transmetallation 45
2241 Preparation of Alkylzinc Reagents by Transmetallation 46
2242 Preparation of Allylic, Benzylic, and Propargylic
Organozinc Reagents by Transmetallation 47
2243 Preparation of Alkenyl, Aryl, and Alkynyl Zinc
Reagents by Transmetallation 48
225 Preparation of Ordinary Organozinc Reagents by
Oxidative-Reductive Transmetallation 50
226 Other Methods for the Preparation of Ordinary
Zinc Reagents 51
2 3 Preparation of Reformatsky and Reformatsky-type Reagents
and 2-Halozincioketones 55
231 Preparation of Reformatsky and Reformatsky-type Reagents
and 2-Halozincioketones by Oxidative Zincation 55
232 Preparation of Organozinc Derivatives of 2-Haloesters
and 2-Haloketones by Halogen-Zinc Exchange 60
233 Preparation of Organozinc Derivatives of 2-Haloesters by
Hydrogen-Zinc Exchange 61
234 Preparation of Organozinc Derivatives of 2-Haloesters by
Transmetallation 61
2 4 Preparation of Zinc Carbenoids 62
241 Preparation of Simmons-Smith and Related Reagents by
Oxidative Zincation 62
242 Preparation of Simmons-Smith and Related Reagents by
Halogen-Zinc Exchange 63
243 Preparation of Simmons-Smith and Related Reagents by
Transmetallation 66
244 Preparation of Simmons-Smith and Related Reagents by
Other Methods 66
2 5 Transmetallation of Organozinc Reagents into Organocopper
Reagents 67
Chapter 3
Addition of Organozinc Reagents to Carbon-Carbon Multiple Bonds
3 1 Addition of Ordinary Organozinc Reagents to Carbon-Carbon
Multiple Bonds 72
311 Addition of Alkylzinc Reagents to Alkenes and Alkynes 72
3111 Addition of Alkylzinc Reagents to Alkenes 72
3112 Addition of Alkylzinc Reagents to Alkynes 74
312 Addition of Allylic, Benzylic, and Propargylic Zinc Reagents
to Alkenes and Alkynes 77
3121 Addition of Allylic and Benzylic Zinc Reagents
to Alkenes 77
3122 Addition of Ally lie and Propargylic Zinc Reagents
toAlkynes 88
3 2 Addition of Reformatsky Reagents to Carbon-Carbon
Multiple Bonds 94
3 3 Addition of Zinc Carbenoids to Carbon-Carbon Multiple Bonds 95
Chapter 4
Addition of Organozinc Reagents to Carbonyl Groups
4 1 Addition of Ordinary Organozinc Reagents to Carbonyl Groups 108
411 Addition of Alkylzinc Reagents to Carbonyl Groups 108
4111 Lewis Acid-Mediated Addition of Mono- and
Dialkylzincs to Carbonyl Compounds and the
Enantioselective Addition of Dialkylzincs to Aldehydes
in the Presence of Chiral Titanium (IV) Complexes 112
4112 Chiral Lewis Base-Catalyzed Enantioselective
Addition of Dialkylzincs to Aldehydes 126
4113 Carbonyl Addition of Perfluoroalkylzinc Halides 135
4114 Carbonyl Addition of 1 ,n- and 1,1 -Dimetallic
Alkylzinc Reagents and Olefmation of Carbonyl
Compounds 139
412 Addition of Allylic, Benzylic, and Propargylic Zinc
Reagents to Carbonyl Groups 146
4121 Addition of Allylic Zinc Reagents to
Carbonyl Groups 146
4122 Addition of Benzylic Zinc Reagents to
Carbonyl Groups 176
4123 Addition of Propargylic Zinc Reagents to
Carbonyl Groups 177
413 Addition of Alkenyl, Aryl, and Alkynyl Zinc Reagents
to Carbonyl Groups 185
4 2 Addition of Reformatsky and Reformatsky-type Reagents
to Carbonyl Groups 192
421 Reformatsky Reactions of 2-Halozincioesters 193
422 Reformatsky Reactions of 2-Halozincioketones,
2-Halozincioamides, and 2-Halozincionitriles 202
Chapter 5
Addition of Organozinc Reagents to Carbon-Nitrogen Multiple Bonds
5 1 Addition of Ordinary Organozinc Reagents to Carbon-Nitrogen
Multiple Bonds 207
511 Addition of Alkylzinc Reagents to Imines 207
512 Addition of Allylic, Benzylic and Propargylic Zinc Reagents to
Carbon-Nitrogen Multiple Bonds 211
5121 Addition of Allylic, Benzylic, and Propargylic
Zinc Reagents to Imines 212
5122 Addition of Allylic Zinc Reagents
to Nitriles 222
513 Addition of Alkenyl, Aryl, and Alkynyl Zinc
Reagents to Imines 223
5 2 Addition of Reformatsky and Reformatsky-type Reagents
to Carbon-Nitrogen Multiple Bonds 224
521 Addition of Reformatsky and Reformatsky-type
Reagents to Imines 224
522 Addition of Reformatsky and Reformatsky-type
Reagents to Nitriles 232
5 3 Addition of Zinc Carbenoids to Carbon-Nitrogen Multiple Bonds 236
Chapter 6
Conjugate Addition of Organozinc Reagents
6 1 Conjugate Addition of Ordinary Organozinc Reagents 237
611 Conjugate Addition of Alkylzinc Reagents 237
6111 Conjugate Addition of Alkylzinc Reagents to
oc,ß-Ethylenic Carbonyl Compounds 237
6112 Conjugate Addition of Alkylzinc Reagents to
cc,ß-Ethylenic Ketones and Esters Bearing a
Leaving Group at the ß-Position 250
6113 Conjugate Addition of Alkylzinc Reagents to
Nitroalkenes 253
6114 Conjugate Addition of Alkylzinc Reagents to
Nitroalkenes Bearing a Leaving Group at the
ß-Position 254
6115 Conjugate Addition of Alkylzinc Reagents to
a,ß-Acetylenic Carbonyl Compounds 256
6116 Conjugate Addition of Alkylzinc Reagents to
a,ß-Acetylenic Esters Bearing a Leaving Group
at the ß-Position 259
612 Conjugate Addition of Allylic, Benzylic, and Propargylic
Zinc Reagents 260
613 Conjugate Addition of Alkenyl and Aryl Zinc Reagents 262
6 2 Conjugate Addition of Reformatsky and Reformatsky-type
Reagents 267
Chapter 7
Substitution at Carbon by Organozinc Reagents
(Coupling Reactions of Organozinc Reagents)
7 1 Substitution at Carbon by Ordinary Organozinc Reagents 274
711 Substitution at Carbon by Alkylzinc Reagents 274
7111 Alkyl Substrates 274
7112 Allylic, Benzylic, and Propargylic Substrates 277
7113 Alkenyl, Aryl, and Alkynyl Substrates 288
7114 Acyl Halides 294
7115 Ring Opening of Epoxides 298
712 Substitution at Carbon by Allylic, Benzylic, and Propargylic
Zinc Reagents 298
7121 Alkyl Substrates 298
7122 Allylic, Benzylic, and Propargylic Substrates 300
7123 Alkenyl, Aryl, and Alkynyl Substrates 303
7124 Acyl Halides 304
7125 Ring Opening of Epoxides 305
713 Substitution at Carbon by Alkenyl, Aryl, and Alkynyl
Zinc Reagents 308
7131 Alkyl Substrates 308
7132 Allylic, Benzylic, and Propargylic Substrates 310
7133 Alkenyl, Aryl, and Alkynyl Substrates 313
7134 Acyl Halides 331
7 2 Substitution at Carbon by Reformatsky and Reformatsky-type Reagents 334
721 Alkyl Substrates 334
722 Allylic, Benzylic, and Propargylic Substrates 340
723 Alkenyl, Aryl, and Alkynyl Substrates 342
724 Acyl Halides 343
725 Ring Opening of Epoxides 343
Chapter 8
Formation of C-H, C-Halogen, C-O, C-S, C-N, C-P, C-Si, C-Ge, C-Sn,
and C-Pb Bonds via Organozinc Reagents, Organozinc-type Reactions
in Aqueous Medium for the Formation of C-C Bonds
8 1 Formation of C-H, C-Halogen, C-O, C-S, C-N, C-P, C-Si, C-Ge,
C-Sn, and C-Pb Bonds via Organozinc Reagents 345
8 2 Organozinc-type Reactions in Aqueous Medium for the
Formation of C-C Bonds 348
References 351
Author Index 375
Subject Index 391
|
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| id | DE-604.BV010992878 |
| illustrated | Not Illustrated |
| indexdate | 2024-07-09T18:02:16Z |
| institution | BVB |
| isbn | 0849391512 |
| language | English |
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| physical | 411 S. |
| publishDate | 1996 |
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| publisher | CRC Press |
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| series2 | New directions in organic and biological chemistry |
| spelling | Erdik, Ender Verfasser aut Organozinc reagents in organic synthesis Ender Erdik Boca Raton [u.a.] CRC Press 1996 411 S. txt rdacontent n rdamedia nc rdacarrier New directions in organic and biological chemistry Composés organiques - Synthèse ram Zinc - Composés organiques ram Organic compounds Synthesis Organozinc compounds Organische Synthese (DE-588)4075695-6 gnd rswk-swf Zinkorganische Verbindungen (DE-588)4190863-6 gnd rswk-swf Zinkorganische Verbindungen (DE-588)4190863-6 s Organische Synthese (DE-588)4075695-6 s DE-604 HEBIS Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=007357876&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Erdik, Ender Organozinc reagents in organic synthesis Composés organiques - Synthèse ram Zinc - Composés organiques ram Organic compounds Synthesis Organozinc compounds Organische Synthese (DE-588)4075695-6 gnd Zinkorganische Verbindungen (DE-588)4190863-6 gnd |
| subject_GND | (DE-588)4075695-6 (DE-588)4190863-6 |
| title | Organozinc reagents in organic synthesis |
| title_auth | Organozinc reagents in organic synthesis |
| title_exact_search | Organozinc reagents in organic synthesis |
| title_full | Organozinc reagents in organic synthesis Ender Erdik |
| title_fullStr | Organozinc reagents in organic synthesis Ender Erdik |
| title_full_unstemmed | Organozinc reagents in organic synthesis Ender Erdik |
| title_short | Organozinc reagents in organic synthesis |
| title_sort | organozinc reagents in organic synthesis |
| topic | Composés organiques - Synthèse ram Zinc - Composés organiques ram Organic compounds Synthesis Organozinc compounds Organische Synthese (DE-588)4075695-6 gnd Zinkorganische Verbindungen (DE-588)4190863-6 gnd |
| topic_facet | Composés organiques - Synthèse Zinc - Composés organiques Organic compounds Synthesis Organozinc compounds Organische Synthese Zinkorganische Verbindungen |
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