Organoselenium chemistry: synthesis and reactions
Gespeichert in:
| Weitere Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Weinheim
Wiley-VCH-Verl.
2012
|
| Schlagworte: | |
| Online-Zugang: | Inhaltstext Inhaltsverzeichnis |
| Beschreibung: | Literaturangaben |
| Beschreibung: | XIV, 448 S. graph. Darst. |
| ISBN: | 9783527329441 3527329447 |
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| 245 | 1 | 0 | |a Organoselenium chemistry |b synthesis and reactions |c ed. by Thomas Wirth |
| 264 | 1 | |a Weinheim |b Wiley-VCH-Verl. |c 2012 | |
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| 856 | 4 | 2 | |m X:MVB |q text/html |u http://deposit.dnb.de/cgi-bin/dokserv?id=3847401&prov=M&dok_var=1&dok_ext=htm |3 Inhaltstext |
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Datensatz im Suchindex
| _version_ | 1805145558515449856 |
|---|---|
| adam_text |
IMAGE 1
CONTENTS
PREFACE XI LIST OF CONTRIBUTOR XIII
1 ELECTROPHILIC SELENIUM 1
CLAUDIO SANTI AND STEFANO SANTORO 1.1 GENERAL INTRODUCTION 1
1.1.1 SYNTHESIS OF ELECTROPHILIC SELENIUM REAGENTS 3 1.1.2 REACTIVITY
AND PROPERTIES 7 1.2 ADDITION REACTIONS TO DOUBLE BONDS 11 1.2.1
ADDITION REACTION INVOLVING OXYGEN-CENTERED NUCLEOPHILES 11 1.2.2
ADDITION REACTION INVOLVING NITROGEN-CENTERED NUCLEOPHILES 22 1.2.3
ADDITION REACTIONS INVOLVING CARBON-CENTERED NUCLEOPHILES 26 1.2.4
ADDITION REACTION INVOLVING CHIRAL NUCLEOPHILES OR CHIRAL
SUBSTRATES 28
1.3 SELENOCYDIZATIONS 30
1.3.1 OXYGEN NUCLEOPHILES 31 1.3.2 NITROGEN NUCLEOPHILES 35 1.3.3
COMPETITION BETWEEN OXYGEN AND NITROGEN NUCLEOPHILES 40 1.3.4 CARBON
NUCLEOPHILES 42
1.3.5 DOUBLE CYDIZATION REACTIONS 44 REFERENCES 45
2 NUCLEOPHILIC SELENIUM 53
MICHIO IWAOKA
2.1 INTRODUCTION 53
2.1.1 DEVELOPMENT OF NUCLEOPHILIC SELENIUM REAGENTS 53 2.1.2 EXAMPLES OF
RECENT APPLICATIONS 54 2.2 PROPERTIES OF SELENOLS AND SELENOLATES 56
2.2.1 ELECTRONEGATIVITY OF SELENIUM 56 2.2.2 TAUTOMERISM OF SELENOLS 57
2.2.3 NUCLEOPHILICITY OF SELENOLATES 58 2.3 INORGANIC NUDEOPHILIC
SELENIUM REAGENTS 59
2.3.1 CONVENTIONAL REAGENTS 59
BIBLIOGRAFISCHE INFORMATIONEN HTTP://D-NB.INFO/1013143973
DIGITALISIERT DURCH
IMAGE 2
VI I CONTENTS
2.3.2 NEW REAGENTS 61 2.4 ORGANIC NUCLEOPHILIC SELENIUM REAGENTS 65 2
A.I PREPARATION 65 2.4.2 STRUCTURE 66 2.4.3 AMMONIUM SELENOLATES (NH 4 +
) 67 2.4.4 SELENOLATES OF GROUP 1 ELEMENTS (LI, NA, K, AND CS) 67 2.4.5
SELENOLATES OF GROUP 2 ELEMENTS (MG, CA, AND BA) 70 2.4.6 SELENOLATES OF
GROUP 3 ELEMENTS (SM, CE, PR, NB, AND U) 71 2.4.7 SELENOLATES OF GROUP 4
ELEMENTS (TI, ZR, AND HF) 73 2.4.8 SELENOLATES OF GROUP 5 ELEMENTS (V,
NB, AND TA) 74
2 A3 SELENOLATES OF GROUP 6 ELEMENTS (MO AND W) 75 2.4.10 SELENOLATES OF
GROUP 7 ELEMENTS (MN AND RE) 76 2.4.11 SELENOLATES OF GROUP 8 ELEMENTS
(FE, RU, AND OS) 78 2.4.12 SELENOLATES OF GROUP 9 ELEMENTS (CO, RH, AND
IR) 81
2.4.13 SELENOLATES OF GROUP 10 ELEMENTS (NI, PD, AND PT) 84 2.4.14
SELENOLATES OF GROUP 11 ELEMENTS (CU, AG, AND AU) 90 2.4.15 SELENOLATES
OF GROUP 12 ELEMENTS (ZN, CD, AND HG) 92 2.4.16 SELENOLATES OF GROUP 13
ELEMENTS (B, AL, GA, AND IN) 95 2.4.17 SELENOLATES OF GROUP 14 ELEMENTS
(SI, GE, SN, AND PB) 97 2.4.18 SELENOLATES OF GROUP 15 ELEMENTS (P, AS,
SB, AND BI) 100
REFERENCES 102
3 SELENIUM COMPOUNDS IN RADICAL REACTIONS 111 W. RUSSELL BOWMAN 3.1
HOMOLYTIC SUBSTITUTION AT SELENIUM TO GENERATE RADICAL PRECURSORS 111
3.1.1 BIMOLECULAR S H 2 REACTIONS: SYNTHETIC CONSIDERATIONS 112 3.1.1.1
RADICAL REAGENTS 115 3.1.2 ALKYL RADICALS FROM SELENIDE PRECURSORS 115
3.1.3 ACYL RADICALS FROM ACYL SELENIDE PRECURSORS 119 3.1.4 IMIDOYL
RADICALS FROM IMIDOYL SELENIDES 123 3.1.5 OTHER RADICALS FROM SELENIDE
PRECURSORS 125 3.2 SELENIDE BUILDING BLOCKS 126 3.3 SOLID-PHASE
SYNTHESIS 128 3.4 SELENIDE PRECURSORS IN RADICAL DOMINO REACTIONS 130
3.5 HOMOLYTIC SUBSTITUTION AT SELENIUM FOR THE SYNTHESIS OF
SE-CONTAINING PRODUCTS 132 3.5.1 INTERMOLECULAR S H 2 ONTO SE 132 3.5.2
INTRAMOLECULAR S H 2: CYDIZATION ONTO SE 132 3.6 SELENO GROUP TRANSFER
ONTO ALKENES AND ALKYNES 134
3.6.1 SELENO-SELENATION 135 3.6.2 SELENO-SULFONATION 136 3.6.3
SELENO-ALKYLATION 137 3.7 PHSEH IN RADICAL REACTIONS 138 3.7.1 RADICAL
CLOCK REACTIONS 138
IMAGE 3
CONTENTS VII
3.7.2 PROBLEM OF UNWANTED TRAPPING OF INTERMEDIATE RADICALS 138
3.7.3 CATALYSIS OF STANNANE-MEDIATED REACTIONS 139 3.8 SELENIUM RADICAL
ANIONS, S RN 1 SUBSTITUTIONS 141 REFERENCES 143
4 SELENIUM-STABILIZED CARBANIONS 147 JOAO V. COMASSETO, ALCINDO A. DOS
SANTOS, AND EDISON P. WENDLER 4.1 INTRODUCTION 147
4.2 PREPARATION OF SELENIUM-STABILIZED CARBANIONS 149 4.2.1
DEPROTONATION OF SELENIDES 149 4.2.2 ELEMENT-LITHIUM EXCHANGE 154 4.2.3
CONJUGATE ADDITION OF ORGANOMETALLICS TO VINYL- AND
ALKYNYLSELENIDES 158 4.3 REACTIVITY OF THE SELENIUM-STABILIZED
CARBANIONS WITH ELECTROPHILES AND SYNTHETIC TRANSFORMATIONS OF THE
PRODUCTS 161 4.3.1 REACTION OF SELENIUM-STABILIZED CARBANIONS WITH
ELECTROPHILES 166 4.3.2 SELENIUM-BASED TRANSFORMATIONS ON THE REACTION
PRODUCTS OF
SELENIUM-STABILIZED CARBANIONS WITH ELECTROPHILES 167 4.4 STEREOCHEMICAL
ASPECTS 168 4A.I CYCLIC SELENIUM-STABILIZED CARBANIONS 173 4.4.2 ACYCLIC
SELENIUM-STABILIZED CARBANIONS I76 4.5 APPLICATION OF
SELENIUM-STABILIZED CARBANIONS IN TOTAL SYNTHESIS I76 4.5.1 EXAMPLES
USING ALKYLATION REACTIONS OF SELENIUM-STABILIZED
CARBANIONS 177
4.5.2 EXAMPLES USING THE ADDITION OF SELENIUM-STABILIZED CARBANIONS TO
CARBONYL COMPOUNDS 180 4.5.3 EXAMPLES USING 1,4-ADDITION OF
SELENIUM-STABILIZED CARBANIONS TO OC,SS-UNSATURATED CARBONYL COMPOUNDS
184 4.6 CONCLUSION 186
REFERENCES 187
5 SELENIUM COMPOUNDS WITH VALENCY HIGHER THAN TWO 191 JOZEF DRABOWICZ,
JAROSIAW LEWKOWSKI, ANDJACEK SDANOWSKI 5.1 INTRODUCTION 191
5.2 TRIVALENT, DICOORDINATED SELENONIUM SALTS 192 5.3 TRIVALENT,
TRICOORDINATED DERIVATIVES 194 5.4 TETRAVALENT, DICOORDINATED
DERIVATIVES 211 5.5 TETRAVALENT, TRICOORDINATED DERIVATIVES 225
5.6 PENTAVALENT DERIVATIVES 239 5.7 HEXAVALENT, TETRACOORDINATED
DERIVATIVES 240 5.8 HYPERVALENT DERIVATIVES 244 5.8.1 SELENURANES 244
5.8.2 SELENURANE OXIDES 249 5.8.3 PERSELENURANES 250 ACKNOWLEDGMENT 251
REFERENCES 251
IMAGE 4
VIII CONTENTS
6 SELENOCARBONYLS 257
TOSHIAKI MURAI
6.1 OVERVIEW 257
6.2 THEORETICAL ASPECTS OF SELENOCARBONYLS 259 6.3 MOLECULAR STRUCTURE
OF SELENOCARBONYLS 261 6.4 SYNTHETIC PROCEDURES OF SELENOCARBONYLS 261
6.5 MANIPULATION OF SELENOCARBONYLS 270 6.6 METAL COMPLEXES OF
SELENOCARBONYLS 278 6.7 FUTURE ASPECTS 280
REFERENCES 281
7 SELENOXIDE ELIMINATION AND [2,3]-SIGMATROPIC REARRANGEMENT 287
YOSHIAKI NISHIBAYASHI AND SAKAE UEMURA 7.1 INTRODUCTION 287
7.2 PREPARATION AND PROPERTIES OF CHIRAL SELENOXIDES 288 7.3 SELENOXIDE
ELIMINATION 292 7.3.1 ENANTIOSELECTIVE SELENOXIDE ELIMINATION PRODUCING
CHIRAL ALIENES AND OC,SS-UNSATURATED KETONES 293
7.3.2 DIASTEREOSELECTIVE SELENOXIDE ELIMINATION PRODUCING CHIRAL
ALLENECARBOXYLIC ESTERS 295 7.4 [2,3]-SIGMATROPIC REARRANGEMENT VIA
ALLYLIC SELENOXIDES 297 7A.I ENANTIOSELECTIVE [2,3]-SIGMATROPIC
REARRANGEMENT PRODUCING CHIRAL
ALLYLIC ALCOHOLS 297 7A.I DIASTEREOSELECTIVE [2,3]-SIGMATROPIC
REARRANGEMENT PRODUCING CHIRAL ALLYLIC ALCOHOLS 299 7.5
[2,3]-SIGMATROPIC REARRANGEMENT VIA ALLYLIC SELENIMIDES 305 7.5.1
PREPARATION AND PROPERTIES OF CHIRAL SELENIMIDES 307
7.5.2 ENANTIOSELECTIVE [2,3]-SIGMATROPIC REARRANGEMENT PRODUCING CHIRAL
ALLYLIC AMINES 309 7.5.3 DIASTEREOSELECTIVE [2,3]-SIGMATROPIC
REARRANGEMENTS PRODUCING CHIRAL ALLYLIC AMINES 310
7.6 [2,3]-SIGMATROPIC REARRANGEMENT VIA ALLYLIC SELENIUM YLIDES 311
7.6.1 PREPARATION AND PROPERTIES OF OPTICALLY ACTIVE SELENIUM YLIDES 312
7.6.2 ENANTIOSELECTIVE [2,3]-SIGMATROPIC REARRANGEMENTS VIA ALLYLIC
SELENIUM YLIDES 313
7.6.3 DIASTEREOSELECTIVE [2,3]-SIGMATROPIC REARRANGEMENT VIA ALLYLIC
SELENIUM YLIDES 315 7.7 SUMMARY 317
REFERENCES 317
8 SELENIUM COMPOUNDS AS LIGANDS AND CATALYSTS 321 FATEH V. SINGH AND
THOMAS WIRTH 8.1 INTRODUCTION 321
8.2 SELENIUM-CATALYZED REACTIONS 321 8.2.1 STEREOSELECTIVE ADDITION OF
DIORGANOZINC REAGENTS TO ALDEHYDES 322
IMAGE 5
CONTENTS IX
8.2.1.1 DIETHYLZINC ADDITION 322
8.2.1.2 DIPHENYLZINC ADDITION 323 8.2.2 SELENIUM-LIGATED TRANSITION
METAL-CATALYZED REACTIONS 324 8.2.2.1 SELENIUM-LIGATED STEREOSELECTIVE
HYDROSILYLATION OF KETONES 324 8.2.2.2 SELENIUM-LIGATED COPPER-CATALYZED
ADDITION OF ORGANOMETALLIC
REAGENTS TO ENONES 325 8.2.2.3 SELENIUM-LIGATED PALLADIUM-CATALYZED
ASYMMETRIC ALLYLIC ALKYLATION 326 8.2.2.4 SELENIUM-LIGANDS IN
PALLADIUM-CATALYZED MIZOROKI-HECK
REACTIONS 328
8.2.2.5 SELENIUM-LIGANDS IN PALLADIUM-CATALYZED PHENYLSELENENYLATION OF
ORGANOHALIDES 330 8.2.2.6 SELENIUM-LIGANDS IN PALLADIUM-CATALYZED
SUBSTITUTION REACTIONS 331 8.2.2.7 SELENIUM-LIGANDS IN THE
PALLADIUM-CATALYZED ALLYLATION OF
ALDEHYDES 331
8.2.2.8 SELENIUM-LIGANDS IN PALLADIUM-CATALYZED CONDENSATION REACTIONS
332 8.2.2.9 RUTHENIUM-CATALYZED SUBSTITUTION REACTIONS 333 8.2.2.10
SELENIUM-LIGANDS IN ZINC-CATALYZED INTRAMOLECULAR
HYDROAMINATIONS 334 8.2.3 SELENIUM-LIGANDS IN ORGANOCATALYTIC ASYMMETRIC
ALDOL REACTIONS 334 8.2.4 SELENIUM-LIGANDS IN STEREOSELECTIVE DARZENS
REACTIONS 334 8.2.5 SELENIUM-CATALYZED CARBONYLATION REACTIONS 335 8.2.6
SELECTIVE REDUCTION OF A,SS-UNSATURATED CARBONYL COMPOUNDS 336 8.2.7
SELENIUM-CATALYZED HALOGENATIONS AND HALOCYCLIZATIONS 336 8.2.8
SELENIUM-CATALYZED STAUDINGER-VILARRASA REACTION 337 8.2.9
SELENIUM-CATALYZED ELIMINATION REACTIONS OF DIOLS 338 8.2.10
SELENIUM-CATALYZED HYDROSTANNYLATION OF ALKENES 339 8.2.11
SELENIUM-CATALYZED RADICAL CHAIN REACTIONS 340 8.2.12 SELENIUM-CATALYZED
OXIDATION REACTIONS 342
8.2.12.1 SELENIUM-CATALYZED EPOXIDATION OF ALKENES 342 8.2.12.2
SELENIUM-CATALYZED DIHYDROXYLATION OF ALKENES 344 8.2.12.3
SELENIUM-CATALYZED OXIDATION OF ALCOHOLS 346 8.2.12.4 BAEYER-VILLIGER
OXIDATION 347 8.2.12.5 SELENIUM-CATALYZED ALLYLIC OXIDATION OF ALKENES
349 8.2.12.6 SELENIUM-CATALYZED OXIDATION OF ARYL ALKYL KETONES 350
8.2.12.7 SELENIUM-CATALYZED OXIDATION OF PRIMARY AROMATIC AMINES 350
8.2.12.8 SELENIUM-CATALYZED OXIDATION OF ALKYNES 351 8.2.12.9
SELENIUM-CATALYZED OXIDATION OF HALIDE ANIONS 352 8.2.13 STEREOSELECTIVE
CATALYTIC SELENENYLATION-ELIMINATION
REACTIONS 353
8.2.14 SELENIUM-CATALYZED DIELS-ALDER REACTIONS 355 8.2.15
SELENIUM-CATALYZED SYNTHESIS OF THIOACETALS 355
IMAGE 6
X I CONTENTS
8.2.16 SELENIUM-CATALYZED BAYLIS-HILLMAN REACTION 356
REFERENCES 356
9 BIOLOGICAL AND BIOCHEMICAL ASPECTS OF SELENIUM COMPOUNDS 361 BHASKARJ.
BHUYAN AND COVINDASAMY MUGESH 9.1 INTRODUCTION 361
9.2 BIOLOGICAL IMPORTANCE OF SELENIUM 361 9.3 SELENOCYSTEINE: THE 21ST
AMINO ACID 362 9.4 BIOSYNTHESIS OF SELENOCYSTEINE 363 9.5 CHEMICAL
SYNTHESIS OF SELENOCYSTEINE 366
9.6 CHEMICAL SYNTHESIS OF SEC-CONTAINING PROTEINS AND PEPTIDES 367 9.7
SELENOENZYMES 369 9.7.1 GLUTATHIONE PEROXIDASES 369 9.7.2 IODOTHYRONINE
DEIODINASE 379
9.7.3 SYNTHETIC MIMICS OF IDS 384 9.7A THIOREDOXIN REDUCTASE 387 9.8
SUMMARY 389
REFERENCES 392
"SE NMR VALUES 397
INDEX 435 |
| any_adam_object | 1 |
| author2 | Wirth, Thomas |
| author2_role | edt |
| author2_variant | t w tw |
| author_facet | Wirth, Thomas |
| building | Verbundindex |
| bvnumber | BV039703000 |
| classification_rvk | VK 7716 |
| classification_tum | CHE 632f |
| ctrlnum | (OCoLC)766000299 (DE-599)DNB1013143973 |
| dewey-full | 547.05724 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.05724 |
| dewey-search | 547.05724 |
| dewey-sort | 3547.05724 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Chemie |
| format | Book |
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| id | DE-604.BV039703000 |
| illustrated | Illustrated |
| indexdate | 2024-07-21T00:15:56Z |
| institution | BVB |
| isbn | 9783527329441 3527329447 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-024551494 |
| oclc_num | 766000299 |
| open_access_boolean | |
| owner | DE-11 DE-91G DE-BY-TUM DE-19 DE-BY-UBM |
| owner_facet | DE-11 DE-91G DE-BY-TUM DE-19 DE-BY-UBM |
| physical | XIV, 448 S. graph. Darst. |
| publishDate | 2012 |
| publishDateSearch | 2012 |
| publishDateSort | 2012 |
| publisher | Wiley-VCH-Verl. |
| record_format | marc |
| spelling | Organoselenium chemistry synthesis and reactions ed. by Thomas Wirth Weinheim Wiley-VCH-Verl. 2012 XIV, 448 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Literaturangaben Organische Synthese (DE-588)4075695-6 gnd rswk-swf Selenorganische Verbindungen (DE-588)4134086-3 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Selenorganische Verbindungen (DE-588)4134086-3 s DE-604 Organische Synthese (DE-588)4075695-6 s Wirth, Thomas edt X:MVB text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3847401&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=024551494&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Organoselenium chemistry synthesis and reactions Organische Synthese (DE-588)4075695-6 gnd Selenorganische Verbindungen (DE-588)4134086-3 gnd |
| subject_GND | (DE-588)4075695-6 (DE-588)4134086-3 (DE-588)4143413-4 |
| title | Organoselenium chemistry synthesis and reactions |
| title_auth | Organoselenium chemistry synthesis and reactions |
| title_exact_search | Organoselenium chemistry synthesis and reactions |
| title_full | Organoselenium chemistry synthesis and reactions ed. by Thomas Wirth |
| title_fullStr | Organoselenium chemistry synthesis and reactions ed. by Thomas Wirth |
| title_full_unstemmed | Organoselenium chemistry synthesis and reactions ed. by Thomas Wirth |
| title_short | Organoselenium chemistry |
| title_sort | organoselenium chemistry synthesis and reactions |
| title_sub | synthesis and reactions |
| topic | Organische Synthese (DE-588)4075695-6 gnd Selenorganische Verbindungen (DE-588)4134086-3 gnd |
| topic_facet | Organische Synthese Selenorganische Verbindungen Aufsatzsammlung |
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