Reactions and syntheses in the organic chemistry laboratory:
Saved in:
| Format: | Book |
|---|---|
| Language: | English |
| Published: |
Weinheim
Wiley-VCH
2015
|
| Edition: | 2., completely rev. and updated ed. |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Item Description: | Hier auch später erschienene, unveränderte Nachdrucke |
| Physical Description: | XXV, 642 S. graph. Darst. |
| ISBN: | 3527338144 9783527338146 |
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MARC
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| 245 | 1 | 0 | |a Reactions and syntheses in the organic chemistry laboratory |c Lutz F. Tietze ... |
| 250 | |a 2., completely rev. and updated ed. | ||
| 264 | 1 | |a Weinheim |b Wiley-VCH |c 2015 | |
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Record in the Search Index
| _version_ | 1804152631234396160 |
|---|---|
| adam_text | CONTENTS
PREFACE TO THE FIRST EDITION IX
PREFACE TO THE SECOND EDITION XIII
ACKNOWLEDGMENTS XV
ABOUT
THE
AUTHORS XVII
ABBREVIATIONS
AND
SYMBOLS XIX
1 C-C BOND FORMATION 1
1.1 NUCLEOPHILIC ADDITION TO ALDEHYDES, KETONES, CARBOXYLIC ACID
DERIVATIVES (ESTERS, ANHYDRIDES), AND A, P-UNSATURATED CARBONYL
COMPOUNDS; CARBONYL OLEFINATION 1
1.1.1 ()-4-ACETOXY-2-METHYL-2-BUTENAL 1
1.1.2 METHYL (S)-5-OXO-3,5-DIPHENYLPENTANOATE 7
1.1.3 ETHYL 8-CHLORO-4-METHYLNAPHTHALENE-2-CARBOXYLATE 13
1.1.4 ()-4-HYDROXY-FLR-HIMACHALAN 19
1.1.5 METHYLENECYCLODODECANE 28
1.2 ALKYLATION OF ALDEHYDES/KETONES, CARBOXYLIC ACIDS, AND
P-DICARBONYL COMPOUNDS 34
1.2.1 (+)-(S)-4-METHYLHEPTAN-3-ONE 34
1.2.2 (S)-2-ISOPROPYLHEX-4-YN-L-OL 39
1.2.3 METHYL 3-OXO-5-PHENYLPENTANOATE 48
1.3 REACTIONS OF THE ALDOL AND MANNICH TYPE SI
1.3.1 (+)-(7AS)-7,7A-DIHYDRO-7A-METHYL-L,5(6H)-INDANEDIONE 51
1.3.2 CYCLOHEXYL 2-BENZOYLAMINO-2-(2-OXOCYCLOHEXYL) ACETATE 57
1.3.3 (S)-L-HYDROXY-L,3-DIPHENYL-3-PROPANONE 64
1.3.4 ETHYL (LS,2/?,6/?)-2-HYDROXY-4-OXO-2,6-DIPHENYLCYCLOHEXANE-L-
CARBOXYLATE 72
1.4 ELECTROPHILIC AND NUCLEOPHILIC ACYLATION 79
1.4.1 (*)-ETHYL (L/?)-L-METHYL-2-OXOCYCLOPENTANE-L-CARBOXYLATE 79
1.4.2 ETHYL (5)- AND (/?)-2-HYDROXY-4-PHENYLBUTANOATE 85
1.4.3 NAPROXEN 92
1.4.4 3-BENZOYLCYCLOHEXANONE 104
1.5 REACTIONS OF ALKENES VIA CARBENIUM IONS 110
1.5.1 PIPERINE 110
HTTP://D-NB.INFO/1050181611
VII CONTENTS
1.5.2 CICLOXILIC ACID 117
1.5.3 P-IONONE 123
1.6 TRANSITION-METAL-CATALYZED REACTIONS 130
1.6.1 ()-4-CHLOROSTILBENE 130
1.6.2 2-CYANOMETHYL-3 ,4 -DIMETHOXYBIPHENYL 136
1.6.3 (2-PHENYLETHYNYL)ANILINE 143
1.6.4 DIETHYL CYCLOPENT-3-ENE-L,L-DICARBOXYLATE AND
1,8-DIOXACYCLOTETRADEC-LL-YNE- 2,7-DIONE 146
1.7 PERICYCLIC REACTIONS 154
1.7.1 TRANYLCYPROMINE 154
1.7.2 LL,LL-DIFLUORO-L,6-METHANO[10]ANNULENE 161
1.7.3 DIMETHYL HEPTALENE-L,2-DICARBOXYLATE 166
1.7.4 DIMETHYL L,8-BISHOMOCUBANE-4,6-DICARBOXYLATE 172
1.7.5 A-TERPINEOL 177
1.7.6 BICYCLO[2.2.2]OCTENE DERIVATIVE 189
1.8 RADICAL REACTIONS 193
1.8.1 ETHYL 4,6,6,6-TETRACHLORO-3,3-DIMETHYLHEXANOATE 193
1.8.2 3-BROMOPHENANTHRENE 198
2 OXIDATION AND REDUCTION 203
2.1 EPOXIDATION OF C=C BONDS 203
2.1.1 SHARPLESS-KATSUKI EPOXIDATION 203
2.1.2 JACOBSEN EPOXIDATION 206
2.2 DIHYDROXYLATION OF C=C BONDS 214
2.2.1 SHARPLESS DIHYDROXYLATION 215
2.3 OXIDATION OF ALCOHOLS TO CARBONYL COMPOUNDS 218
2.3.1 SWERN OXIDATION 220
2.3.2 DESS- MARTIN OXIDATION 222
2.3.3 PERRUTHENATE OXIDATION 225
2.3.4 TEMPO OXIDATION 227
2.4 ENANTIOSELECTIVE REDUCTION OF KETONES 229
2.4.1 BINAL-H REDUCTION OF BUTYROPHENONE 232
2.4.2 CBS REDUCTION OF ACETOPHENONE 234
2.5 BIOMIMETIC REDUCTIVE AMINATION 239
2.5.1 SYNTHESIS OF BENZYL-4-METHOXYPHENYLAMINE 239
2.6 ENANTIOSELECTIVE WACKER OXIDATION 242
2.6.1 (S)-5-METHOXY-2,7-DIMETHYL-2-VINYLCHROMAN 242
3 HETEROCYCLIC COMPOUNDS 257
3.1 THREE-AND FOUR-MEMBERED HETEROCYCLES 257
3.1.1 (S)-PROPRANOLOL 257
3.1.2 OXETANE DERIVATIVE 263
3.1.3 AZETIDIN-2-ONE DERIVATIVE 267
3.2 FIVE-MEMBERED HETEROCYCLES 272
3.2.1 2,4-DIPHENYLFURAN 272
CONTENTS VII
3.2.2 3,4-DIMETHYLPYRROLE 278
3.2.3 4,6-DIMETHOXYBENZO[]THIOPHENE 286
3.2.4 2-PHENYLINDOLE 293
3.2.5 MELATONIN 297
3.2.6 3-(4-METHYLBENZOYLAMINO)-L-PHENYL-4,5-DIHYDROPYRAZOLE 304
3.2.7 CAMALEXIN 309
3.3 SIX-MEMBERED HETEROCYCLES 315
3.3.1 AZINE AND DIAZINE SYNTHESES WITH ACETOACETATE 315
3.3.2 (/?)-SALSOLIDINE 322
3.3.3 EPIRIZOLE 329
3.3.4 RAS FARNESYLTRANSFERASE INHIBITOR 334
3.3.5 ()-DIHYDREXIDINE 344
3.4 CONDENSED HETEROCYCLES 355
3.4.1 6-ETHOXYCARBONYLNAPHTHO[2,3-A]INDOLIZINE-7,12-QUINONE 355
3.4.2 EGF-R-PYRROLO[2,3-D]PYRIMIDINE 364
3.4.3 7-PHENYL-L,6-NAPHTHYRIDINE 370
3.4.4 CAFFEINE 375
3.4.5 NEDOCROMIL ANALOGON 381
3.4.6 HIGH-PRESSURE REACTION 391
3.5 OTHER HETEROCYCLIC SYSTEMS, HETEROCYCLIC DYES 398
3.5.1 DIBENZOPYRIDINO[18]CROWN-6 398
3.5.2 INDIGO 404
3.5.3 PYRVINIUM IODIDE 408
3.5.4 2,3.7,8,12,13,17,18-OCTAMETHYLPORPHYRIN 416
3.5.5 SYNTHESIS OF A ROTAXANE 419
4 SELECTED NATURAL PRODUCTS 425
4.1 ISOPRENOIDS 425
4.1.1 NEROL 429
4.1.2 (*)-MENTHOL 436
4.1.3 ARTEMISIA KETONE 441
4.1.4 VETICADINOL 445
4.1.5 ALL-TRANS-VITAMIN A ACETATE 456
4.2 CARBOHYDRATES 464
INTRODUCTION 464
4.2.1 SYNTHESIS OF GLUCOSYL DONORS 467
4.2.2 GLYCOSYLATIONS OF GLUCOSYL DONORS WITH CYCLOPENTANOL 474
4.3 AMINO ACIDS AND PEPTIDES 478
INTRODUCTION 478
4.3.1 A/-BOC-A/-METHYL-(S)-ALANYL NUCLEO AMINO ACID 483
4.3.2 AMINO ACID RESOLUTION WITH AMINO ACYLASE 488
4.3.3 Y, 6-UNSATURATED A-AMINO ACIDS 494
4.3.4 PASSERINI HYDROXYAMIDE 500
4.3.5 ASPARTAME 508
4.3.6 UGI DIPEPTIDE ESTER 5I6
VIII CONTENTS
4.3.7 SOLID-PHASE SYNTHESIS OF P-PEPTIDES 521
4.4 NUCLEOTIDES AND OLIGONUCLEOTIDES 527
INTRODUCTION 5 27
4.4.1 2 ,3 -DIBENZOYL-6 -0-DMTR-P-D-GLUCOPYRANOSYL-URACIL
4 -0-PHOSPHORAMIDITE 531
4.4.2 SOLID-PHASE SYNTHESIS OF NUCLEIC ACIDS 542
5 DOMINO REACTIONS 549
5.1 DOMINO REACTIONS IN SYNTHETIC METHODOLOGY 552
5.1.1 (/?)-METHYL 4-[(/?)-L,2-DIPHENYLETHOXY]-4-METHYLHEPT-6-ENOATE 552
5.1.2 OLIVETOL 558
5.2 DOMINO REACTIONS IN THE SYNTHESIS OF ALKALOIDS 562
5.2.1 HIRSUTINE 566
5.2.2 RAC-2,3-DIMETHOXYBERBINE 579
5.2.3 BUFLAVINE 586
5.3 DOMINO REACTIONS IN THE SYNTHESIS OF ISOPRENOIDS 593
5.3.1 ()-TRAWS-CHRYSANTHEMIC ACID 593
5.4 DOMINO REACTIONS FOR THE SYNTHESIS OF CHROMANS AND DIOXINS 601
5.4.1 METHYL [(S)-5-METHOXY-2,7-DIMETHYL-2-CHROMAN-2-YL] ACETATE 601
5.4.2 (RAC)-()-5-(2-METHYL-2,3-DIHYDROBENZO[6][L,4]DIOXIN-2-YL)-PENT-3-
ENE-2-ONE 607
5.5 DOMINO REACTIONS IN THE SYNTHESIS OF CHIROPTICAL SWITCHES 611
5.5.1 L-(9/F-XANTHEN-9-YLIDENE)-2,3-DIHYDRO-L//-INDEN-2-OL 611
I NDEX OF REACTIONS 623
INDEX OF PRODUCTS 627
SUBJECT INDEX 635
|
| any_adam_object | 1 |
| author_GND | (DE-588)123655315 |
| building | Verbundindex |
| bvnumber | BV042144288 |
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| ctrlnum | (OCoLC)878979281 (DE-599)DNB1050181611 |
| dewey-full | 547.2072 |
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| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.2072 |
| dewey-search | 547.2072 |
| dewey-sort | 3547.2072 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Chemie |
| edition | 2., completely rev. and updated ed. |
| format | Book |
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| genre | 1\p (DE-588)4123623-3 Lehrbuch gnd-content 2\p (DE-588)4127380-1 Praktikum gnd-content |
| genre_facet | Lehrbuch Praktikum |
| id | DE-604.BV042144288 |
| illustrated | Illustrated |
| indexdate | 2024-07-10T01:13:47Z |
| institution | BVB |
| isbn | 3527338144 9783527338146 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-027584201 |
| oclc_num | 878979281 |
| open_access_boolean | |
| owner | DE-703 DE-355 DE-BY-UBR DE-20 DE-11 DE-29T DE-91G DE-BY-TUM DE-19 DE-BY-UBM DE-83 |
| owner_facet | DE-703 DE-355 DE-BY-UBR DE-20 DE-11 DE-29T DE-91G DE-BY-TUM DE-19 DE-BY-UBM DE-83 |
| physical | XXV, 642 S. graph. Darst. |
| publishDate | 2015 |
| publishDateSearch | 2015 |
| publishDateSort | 2015 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Reactions and syntheses in the organic chemistry laboratory Lutz F. Tietze ... 2., completely rev. and updated ed. Weinheim Wiley-VCH 2015 XXV, 642 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Hier auch später erschienene, unveränderte Nachdrucke Organische Chemie (DE-588)4043793-0 gnd rswk-swf Präparative organische Chemie (DE-588)4121505-9 gnd rswk-swf Organische Synthese (DE-588)4075695-6 gnd rswk-swf 1\p (DE-588)4123623-3 Lehrbuch gnd-content 2\p (DE-588)4127380-1 Praktikum gnd-content Organische Synthese (DE-588)4075695-6 s 3\p DE-604 Organische Chemie (DE-588)4043793-0 s 4\p DE-604 Präparative organische Chemie (DE-588)4121505-9 s 5\p DE-604 Tietze, Lutz F. 1942- Sonstige (DE-588)123655315 oth Erscheint auch als Online-Ausgabe, EPUB 978-3-527-68874-6 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-68873-9 Erscheint auch als Online-Ausgabe, PDF 978-3-527-68872-2 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027584201&sequence=000001&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 4\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk 5\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk |
| spellingShingle | Reactions and syntheses in the organic chemistry laboratory Organische Chemie (DE-588)4043793-0 gnd Präparative organische Chemie (DE-588)4121505-9 gnd Organische Synthese (DE-588)4075695-6 gnd |
| subject_GND | (DE-588)4043793-0 (DE-588)4121505-9 (DE-588)4075695-6 (DE-588)4123623-3 (DE-588)4127380-1 |
| title | Reactions and syntheses in the organic chemistry laboratory |
| title_auth | Reactions and syntheses in the organic chemistry laboratory |
| title_exact_search | Reactions and syntheses in the organic chemistry laboratory |
| title_full | Reactions and syntheses in the organic chemistry laboratory Lutz F. Tietze ... |
| title_fullStr | Reactions and syntheses in the organic chemistry laboratory Lutz F. Tietze ... |
| title_full_unstemmed | Reactions and syntheses in the organic chemistry laboratory Lutz F. Tietze ... |
| title_short | Reactions and syntheses in the organic chemistry laboratory |
| title_sort | reactions and syntheses in the organic chemistry laboratory |
| topic | Organische Chemie (DE-588)4043793-0 gnd Präparative organische Chemie (DE-588)4121505-9 gnd Organische Synthese (DE-588)4075695-6 gnd |
| topic_facet | Organische Chemie Präparative organische Chemie Organische Synthese Lehrbuch Praktikum |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027584201&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT tietzelutzf reactionsandsynthesesintheorganicchemistrylaboratory |