Cyclopropanes in organic synthesis:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Hoboken, NJ
Wiley
[2015]
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis Klappentext |
| Beschreibung: | Includes bibliographical references and index |
| Beschreibung: | x, 418 Seiten Diagramme |
| ISBN: | 9781118057438 |
Internformat
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| 245 | 1 | 0 | |a Cyclopropanes in organic synthesis |c Oleg G. Kulinkovich, Belarusian State University, Minsk, Belarus |
| 264 | 1 | |a Hoboken, NJ |b Wiley |c [2015] | |
| 264 | 4 | |c © 2015 | |
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| 500 | |a Includes bibliographical references and index | ||
| 650 | 4 | |a Cyclopropane | |
| 650 | 4 | |a Propane | |
| 650 | 4 | |a Organic compounds |x Synthesis | |
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Datensatz im Suchindex
| _version_ | 1804175826419187712 |
|---|---|
| adam_text | CONTENTS
PREFACE ix
PARTI REACTIVITY AND AVAILABILITY 1
Introduction, 1
Reference, 2
1 Structure and Reactivity of the Cyclopropane Species 3
1.1 Geometry and Bonding, 3
1.2 Energy, 4
1.3 Spectra, 5
1.4 Cyclopropyl Cations, 5
1.5 Cydopropyl Anions, 6
1.6 Cyclopropyl Radicals, 7
1.7 Cyclopropylidenes, 7
1.8 Cyclopropylcarbinyl Cations, 8
1.9 Cyclopropylcarbinyl Anions, 8
1.10 Cyclopropylcarbinyl Radicals, 10
1.11 Cyclopropylcarbenes, 10
1.12 Conclusion, 11
References, 13
2 Ring Cleavage Reactions 15
2.1 Cyclopropyl Activation, 16
2.1.1 Halogen, Ox y, and Sulfur Substituted Cyclopropanes, 16
2.1.2 Alkylidenecyclopropanes, 19
v
vi
CONTENTS
2.2 Cyclopropylcarbinyl Activation, 23
2.2.1 Haiogeno, Oxy, Acyl and Metallomethyl Cyclopropanes, 23
2.2.2 Alkylidenecyclopropanes, 27
2.2.3 Vinyl and Ethynyl Cyclopropanes, 29
2.2.4 1,2-Divinylcyclopropanes, 33
2.2.5 Acceptor Cyclopropanes, 35
2.2.6 Donor Cyclopropanes, 38
2.2.7 Donor-Acceptor Cyclopropanes, 43
2.3 Conclusion, 48
References, 49
3 Synthesis of Cyclopropanes 57
3.1 1,3-Cyclization Reactions, 57
3.1.1 Cyclizations with Cleavage of Two Single Bonds, 58
3.1.2 Cyclizations with Cleavage of One Double Bond and One Single Bond, 59
3.1.3 Cyclizations with Cleavage of Two Double Bonds, 62
3.2 (2 +1 ] Cyclization Reactions, 65
3.2.1 Cycloaddition of Carbene Equivalents to Olefins, 66
3.2.2 Coupling of 1,1-Carbodianion and 1,2-Carbodication Equivalents, 79
3.2.3 Coupling of 1,1-Carbodication and 1,2-Carbodianion Equivalents, 83
3.3 Addition Reactions to the Double Bond of Cyclopropenes, 88
3.4 Interconversion of Cyclopropanes, 90
3.5 Conclusion, 90
References, 90
PART II SYNTHETIC APPLICATION 99
Introduction, 99
References, 100
4 Triangulation Retrosynthetic Analysis 103
4.1 Retrosynthetic Triangulation, 103
4.2 Conclusion, 108
References, 108
5 Acyclic Compounds 109
5.1 Formation of Carbon Substituents, 109
5.1.1 Nonactivated Cyclopropane Precursors, 109
5.1.2 Cyclopropylcarbinyl Activated Precursors, 112
5.1.3 Cooperatively Activated Precursors, 138
5.2 Formation of Olefin Groups, 139
5.2.1 Cyclopropylcarbinyl Activated Precursors, 139
5.2.2 Cyclopropyl Activated Precursors, 142
5.2.3 Fragmentation of the Cyclopropane Precursors, 146
5.2.4 Cooperatively Activated Cyclopropane Precursors, 147
5.3 Formation of Carbonyl Groups, 151
5.3.1 Cyclopropylcarbinyl Precursors, 151
5.3.2 Cooperatively Activated Precursors, 156
5.4 Retrosynthetic Account, 162
References, 163
CONTENTS
6 Cyclobutane Derivatives
6.1 Grandisol Syntheses, 167
6.2 Cyclobutane Synthetic Intermediates, 169
6.3 Retrosynthetic Account, 183
References, 184
7 Cydopentanes
7.1 Vinylcyciopropane-Cyclopentene Rearrangement, 187
7.1.1 Cyclopropylcarbinyl Activated Precursors, 187
7.1.2 Cooperatively Activated Precursors, 188
7.2 Cycloaddition Reactions, 221
7.2.1 Cyclopropylcarbinyl Activated Precursors, 221
7.2.2 Cooperatively Activated Precursors, 221
7.3 Modification of Substituents, 223
7.3.1 Nonactivated Cyclopropane Precursors, 223
7.3.2 Cyclopropylcarbinyl Activated Precursors, 224
7.3.3 Cooperatively Activated Precursors, 231
7.3.4 Fragmentation Reactions, 245
7.4 Retrosynthetic Account, 246
References, 246
8 Cyclohexanes
8.1 Intramolecular Cyclization Reactions, 251
8.2 Cycloaddition Reactions, 255
8.3 Modification of Substituents, 269
8.3.1 Cyclopropylcarbinyl Activated Precursors, 269
8.3.2 Cyclopropyl Activated Precursors, 275
8.3.3 Cooperatively Activated Precursors, 277
8.4 Retrosynthetic Account, 282
References, 283
9 Cycloheptanes
9.1 Divinyicyclopropane-Cycloheptadiene Rearrangement, 285
9.2 Cycloaddition Reactions, 315
9.3 Modification of Substituents, 318
9.3.1 Nonactivated Cyclopropane Precursors, 318
9.3.2 Cyclopropylcarbinyl Activated Precursors, 318
9.3.3 Cyclopropyl Activated Precursors, 323
9.3.4 Cooperatively Activated Precursors, 325
9.4 Retrosynthetic Account, 329
References, 330
10 Cyclooctanes and Larger Carbocycles
10.1 Cycloaddition Reactions, 333
10.2 Modification of Substituents, 334
10.2.1 Cyclopropylcarbinyl Activated Precursors, 334
10.2.2 Cyciopropyl Activated Precursors, 338
10.3 Retrosynthetic Account, 340
References, 340
CONTENTS
11 Heterocyclic Compounds 341
11.1 Intramolecular Cyclization Reactions, 341
11.1.1 Nonactivated Cyclopropane Precursors, 341
11.1.2 Cyclopropylcarbinyl Activated Precursors, 342
11.1.3 Cyclopropyl Activated Precursors, 378
11.1.4 Cooperatively Activated Precursors, 380
11.2 Cycloaddition Reactions, 387
11.2.1 Cyclopropylcarbinyl Activated Precursors, 387
11.2.2 Cooperatively Activated Precursors, 390
11.3 Modification of Substituents, 400
11.3.1 Cyclopropylcarbinyl Activated Substrates, 400
11.3.2 Cyclopropyl Activated Substrates, 402
11.3.3 Cooperatively Activated Substrates, 402
11.4 Retrosymhetic Account, 409
References, 410
CONCLUSION 415
AUTHOR INDEX
417
Used in total synthesis of natural products and other complex molecules, cyclopropanes
can be conveniently prepared with different approaches and used as intermediates to
make target-directed organic transformations more efficient. The synthetic potential of
cyclopropane derivatives is often overlooked but is nonetheless universal and could be
more efficient than standard approaches.
This book provides a comprehensive review of cyclopropanes - their properties,
preparation, synthesis, and applications. It includes comprehensive references and
synopses of review articles on experimental data and theoretical interpretations of the
geometry of cyclopropanes and also discusses typical transformations of substituted
cyclopropanes, derivatives, and intermediates, with emphasis on highly selective
transformations of easily available cyclopropane precursors. The author provides a
detailed description of successful applications of cyclopropane approaches in tafg^t-
oriented syntheses classified by the class of the target structures and transformation
type, and mode of activation of the cyclopropane ring toward its cleavage.
Overall, the book stresses universality, experimental efficiency, and the strategic
importance of synthetic methodologies based on an efficient preparation of cyclopropane
derivatives and their involvement in smooth ring opening or fragmentation reactions
with inexpensive reagents. A valuable guide for practicing chemists, this book offers key
features that include:
• A resource to help readers better understand cyclopropane applications for the
efficient realization of synthetically important organic transformations and popular
experimental procedures
• New developments and up-to-date information that will lead to original
methodologies for complex organic synthesis
• Focus on the synthetic potential of cyclopropane applications, as well as on their
planning by retrosynthetic analysis
Oleg G. Kulinkovich was the head of the Department of Organic Chemistry from 1993-
2003 and the head of the Laboratory of Organoelement Synthesis at Belarusian State
University and visiting professor at Tallinn University of Technology. His seminal work
on titanium-catalyzed cyclopropanation of carboxylic esters with Grignard reagents
bearing 6-hydrogen atoms (Kulinkovich reaction) is very well-known. Dr. Kulinkovich
has published several reviews and original articles on organic synthesis in leading
international journals.
Cover Image: Courtesy of
Oleg Kulinkovich and image design
Subscribe to our free Chemistry eNewsletter at courtesy of Sergey Kulinkovich.
wiley.com/enewsletters
www.wiley.com
Wiley
|
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| spelling | Kulinkovich, Oleg G. 1948- Verfasser (DE-588)1081902310 aut Cyclopropanes in organic synthesis Oleg G. Kulinkovich, Belarusian State University, Minsk, Belarus Hoboken, NJ Wiley [2015] © 2015 x, 418 Seiten Diagramme txt rdacontent n rdamedia nc rdacarrier Includes bibliographical references and index Cyclopropane Propane Organic compounds Synthesis Organische Synthese (DE-588)4075695-6 gnd rswk-swf Cyclopropan (DE-588)4148622-5 gnd rswk-swf Organische Synthese (DE-588)4075695-6 s Cyclopropan (DE-588)4148622-5 s 1\p DE-604 Digitalisierung UB Bayreuth - ADAM Catalogue Enrichment application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=028715715&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis Digitalisierung UB Bayreuth - ADAM Catalogue Enrichment application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=028715715&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA Klappentext 1\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk |
| spellingShingle | Kulinkovich, Oleg G. 1948- Cyclopropanes in organic synthesis Cyclopropane Propane Organic compounds Synthesis Organische Synthese (DE-588)4075695-6 gnd Cyclopropan (DE-588)4148622-5 gnd |
| subject_GND | (DE-588)4075695-6 (DE-588)4148622-5 |
| title | Cyclopropanes in organic synthesis |
| title_auth | Cyclopropanes in organic synthesis |
| title_exact_search | Cyclopropanes in organic synthesis |
| title_full | Cyclopropanes in organic synthesis Oleg G. Kulinkovich, Belarusian State University, Minsk, Belarus |
| title_fullStr | Cyclopropanes in organic synthesis Oleg G. Kulinkovich, Belarusian State University, Minsk, Belarus |
| title_full_unstemmed | Cyclopropanes in organic synthesis Oleg G. Kulinkovich, Belarusian State University, Minsk, Belarus |
| title_short | Cyclopropanes in organic synthesis |
| title_sort | cyclopropanes in organic synthesis |
| topic | Cyclopropane Propane Organic compounds Synthesis Organische Synthese (DE-588)4075695-6 gnd Cyclopropan (DE-588)4148622-5 gnd |
| topic_facet | Cyclopropane Propane Organic compounds Synthesis Organische Synthese Cyclopropan |
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