Organic Mechanisms: reactions, stereochemistry and synthesis
Gespeichert in:
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| Format: | Buch |
| Sprache: | English German |
| Veröffentlicht: |
Berlin ; Heidelberg
Springer
[2010]
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| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | xxxii, 855 Seiten Illustrationen (teilweise farbig) |
| ISBN: | 9783642036507 |
Internformat
MARC
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| 100 | 1 | |a Brückner, Reinhard |d 1955- |e Verfasser |0 (DE-588)129496723 |4 aut | |
| 245 | 1 | 0 | |a Organic Mechanisms |b reactions, stereochemistry and synthesis |c Reinhard Bruckner; edited by Michael Harmata; with foreword by Paul A. Wender |
| 264 | 1 | |a Berlin ; Heidelberg |b Springer |c [2010] | |
| 264 | 4 | |c © 2010 | |
| 300 | |a xxxii, 855 Seiten |b Illustrationen (teilweise farbig) | ||
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Datensatz im Suchindex
| _version_ | 1804141152774914048 |
|---|---|
| adam_text | CONTENTS 1 RADICAL SUBSTITUTION REACTIONS AT THE SATURATED C ATOM 1 1.1
BONDING AND PREFERRED GEOMETRIES IN CARBON RADICALS, CARBENIUM IONS AND
CARBANIONS 2 1.1.1 PREFERRED GEOMETRIES 3 1.1.2 BONDING 4 1.2
STABILITYOF RADICALS 5 1.2.1 REACTIVE RADICALS 6 1.2.2 UNREACTIVE
RADICALS 10 1.3 RELATIVE RATES OFANALOGOUS RADICAL REACTIONS 12 1.3.1
THE BELL - EVANS-POLANYI PRINCIPLE 12 1.3.2 THE HAMMOND POSTULATE 14 1.4
RADICAL SUBSTITUTION REACTIONS: CHAIN REACTIONS 15 1.5 RADICAL
INITIATORS 17 1.6 RADICAL CHEMISTRY OF ALKYLMERCURY(II) HYDRIDES 18 1.7
RADICAL HALOGENATION OF HYDROCARBONS 21 1.7.1 SIMPLE AND MULTIPLE
CHLORINATIONS 21 1.7.2 REGIOSELECTIVITY OF RADICAL CHLORINATIONS 23
1.7.3 REGIOSELECTIVITY OF RADICAL BROMINATIONS COMPARED TO CHLORINATIONS
25 1.7.4 RATE LAW FOR RADICAL HALOGENATIONS; REACTIVITY/SELECTIVITY
PRINCIPLE AND THE ROAD TO PERDITION 27 1.7.5 CHEMOSELECTIVITY OF RADICAL
BROMINATIONS 29 1.7.6 RADICAL CHAIN CHLORINATION USING SULFURYL CHLORIDE
35 1.8 AUTOXIDATIONS 38 1.9 SYNTHETICALLY USEFIIL RADICAL SUBSTITUTION
REACTIONS 41 1.9.1 SIMPLE REDUCTIONS 41 1.9.2 FORMATION OF 5-HEXENYL
RADICALS: COMPETING CYCLOPENTANE FORMATION 44 1.10 DIAZENE
FRAGMENTATIONS AS NOVEL ALKANE SYNTHESES 46 2 NUCLEOPHUEIC SUBSTITUTION
REACTIONS AT THE SATURATED C ATOM 5 BIBLIOGRAFISCHE INFORMATIONEN
HTTP://D-NB.INFO/995947813 DIGITALISIERT DURCH CONTENTS 2.4.3 A REFINED
TRANSITION STATE MODEL FOR THE S N 2 REACTION; CROSSOVER EXPERIMENT AND
ENDOCYCLIC RESTRICTION TEST 63 2.4.4 SUBSTITUENT EFFECTS ON S N 2
REACTIVITY 66 2.5 S N 1 REACTIONS: KINETIC AND STEREOCHEMICAL ANALYSIS;
SUBSTITUENT EFFECTS ON REACTIVITY 69 2.5.1 ENERGY PROFILE AND RATE LAW
OF S N 1 REACTIONS; STEADY STATE APPROXIMATION 69 2.5.2 STEREOCHEMISTRY
OF S N 1 REACTIONS; ION PAIRS 72 2.5.3 SOLVENT EFFECTS ON S N 1
REACTIVITY 73 2.5.4 SUBSTITUENT EFFECTS ONS N L REACTIVITY 76 2.6 WHEN
DO S N REACTIONS AT SATURATED C ATOMS TAKE PLACE ACCORDING TO THE S N 1
MECHANISM AND WHEN DO THEY TAKE PLACE ACCORDING TO THE S N 2 MECHANISM?
83 2.7 GETTING BY WITH HELP FROM FRIENDS, OR A LEAST NEIGHBORS:
NEIGHBORING GROUP PARTICIPATION 83 2.7.1 CONDITIONS FOR AND FEATURES OF
S N REACTIONS WITH NEIGHBORING GROUP PARTICIPATION 83 2.7.2 INCREASED
RATE THROUGH NEIGHBORING GROUP PARTICIPATION 85 2.7.3 STEREOSELECTIVITY
THROUGH NEIGHBORING GROUP PARTICIPATION 86 2.8 S N I REACTIONS 89 2.9
PREPARATIVELY USEFUL S N 2 REACTIONS: ALKYLATIONS 91 3 3.4.4 THOUGHT
EXPERIMENTS II AND III ON THE HYDROBORATION OF CHIRAL ALKENES WITH
CHIRAL BORANES: REAGENT CONTROL OF DIASTEREOSELEC- TIVITY,
MATCHED/MISMATCHED PAIRS, DOUBLE STEREODIFFERENTIATION. . . 133 3.4.5
THOUGHT EXPERIMENT IV ON THE HYDROBORATION OF CHIRAL OLEFINS WITH CHIRAL
DIALKYLBORANES: KINETIC RESOLUTION 134 3.4.6 CATALYTIC ASYMMETRIE
SYNTHESIS: SHARPLESS OXIDATIONS OF ALLYLIC ALCOHOLS 136 3.5 ADDITIONS
THAT TAKE PLACE DIASTEREOSELECTIVELY AS FRANS-ADDITIONS (ADDITIONS VIA
ONIUM INTERMEDIATES) 142 3.5.1 ADDITION OF HALOGENS 144 3.5.2 THE
FORMATION OF HALOHYDRINS; HALOLACTONIZATION AND HALOETHERIFICATION 144
3.5.3 SOLVOMERCURATION OF ALKENES: HYDRATION OF C=C DOUBLE BONDS THROUGH
SUBSEQUENT REDUCTION 148 3.6 ADDITIONS THAT TAKE PLACE OR CAN TAKE PLACE
WITHOUT STEREOCONTROL DEPENDING ON THE MECHANISM 150 3.6.1 ADDITIONS VIA
CARBENIUM ION INTERMEDIATES 150 3.6.2 ADDITIONS VIA CARBANION
INTERMEDIATES 152 4 SS-ELIMINATIONS 157 4.1 CONCEPTS OF ELIMINATION
REACTIONS 157 4.1.1 THE CONCEPTS OF A,SS- AND 1,-ELIMINATION 157 4.1.2
THE TERMS SYN- AND ANFT-ELIMINATION 158 4.1.3 WHEN ARE SYN- AND
ANTT -SELECTIVE ELIMINATIONS STEREOSELECTIVE? . . 159 4.1.4 FORMATION OF
REGIOISOMERIC ALKENES BY SS-ELIMINATION: SAYTZEFF AND HOFMANN PRODUCT(S)
161 4.1.5 THE SYNTHETIC VALUE OF HET /HET 2 IN COMPARISON TO
H/HET-ELIMINATION 4.6.2 NONUNIMOLECULAR EL CB ELIMINATIONS: ENERGY
PROFILE AND RATE LAW . 190 4.6.3 ALKENE-FORMING STEP OF THE
JULIA-LYTHGOE OLEFINATION 191 4.6.4 EL CB ELIMINATIONS IN PROTECTING
GROUP CHEMISTRY 192 4.7 SS-ELIMINATIONSOFHET /HET 2 194 4.7.1
FRAGMENTATIONOFB-HETEROSUBSTITUTEDORGANOMETALLICCOMPOUNDS . 194 4.7.2
PETERSON OLEFINATION 195 4.7.3 OXAPHOSPHETANE FRAGMENTATION, LAST STEP
OF WITTIG AND HORNER-WADSWORTH-EMMONS REACTIONS 196 5 SUBSTITUTION
REACTIONS ON AROMATIC COMPOUNDS 201 5.1 ELECTROPHILIC AROMATIC
SUBSTITUTIONS VIA SIGMA COMPLEXES ( AR-SE REACTIONS ) 201 5.1.1
MECHANISM: SUBSTITUTION OF H VS IPSO-SUBSTITUTION 201 5.1.2
THERMODYNAMIC ASPECTS OFAR-S E REACTIONS 205 5.1.3 KINETIC ASPECTS OF
AR-S E REACTIONS: REACTIVITY AND REGIOSELECTIVITY IN REACTIONS OF
ELECTROPHILES WITH SUBSTITUTED BENZENES 209 5.2 AR-S E REACTIONS VIA
SIGMA COMPLEXES: INDIVIDUAL REACTIONS 215 5.2.1 AR*HAI BOND FORMATION
BYAR-S E REACTION 215 5.2.2 AR*SO 3 H BOND FORMATION BY AR-S E REACTION
218 5.2.3 AR*NO 2 BOND FORMATION BY AR-S E REACTION 219 5.2.4 AR*N=N
BOND FORMATION BYAR-S E REACTION 223 5.2.5 AR*ALKYL BOND FORMATIONS BY
AR-S E 6.2.1 MECHANISM AND RATE LAWS OF S N REACTIONS AT THE CARBOXYL
CARBON 262 6.2.2 S N REACTIONS AT THE CARBOXYL CARBON: THE INFLUENCE OF
RESONANCE STABILIZATION OF THE REACTING C=O DOUBLE BOND ON THE
REACTIVITY OF THE ACYLATING AGENT 268 6.2.3 S N REACTIONS AT THE
CARBOXYL CARBON: THE INFLUENCE OF THE STABILIZATION OF THE TETRAHEDRAL
INTERMEDIATE ON THE REACTIVITY . . . 272 6.3 ACTIVATION OF CARBOXYLIC
ACIDS AND OF CARBOXYLIC ACID DERIVATIVES 274 6.3.1 ACTIVATION OF
CARBOXYLIC ACIDS AND CARBOXYLIC ACID DERIVATIVES IN EQUILIBRIUM
REACTIONS 274 6.3.2 CONVERSION OF CARBOXYLIC ACIDS INTO ISOLABLE
ACYLATING AGENTS. . . 275 6.3.3 COMPLETE IN SITU ACTIVATION OF
CARBOXYLIC ACIDS 278 6.4 SELECTED S N REACTIONS OF HETEROATOM
NUCLEOPHILES AT THE CARBOXYL CARBON . 282 6.4.1 HYDROLYSIS AND
ALCOHOLYSIS OF ESTERS 287 6.4.2 LACTONE FORMATION FRORN
HYDROXYCARBOXYLIC ACIDS 293 6.4.3 FORMING PEPTIDE BONDS 296 6.4.4 S N
REACTIONS OF HETEROATOM NUCLEOPHILES WITH CARBONIC ACID DERIVATIVES 300
6.5 S N REACTIONS OF HYDRIDE DONORS, ORGANOMETALLICS, AND HETEROATOM-
STABILIZED CARBANIONS ON THE CARBOXYL CARBON 306 6.5.1 WHEN DO PURE
ACYLATIONS SUCCEED WITH CARBOXYLIC ACID (DERIVATIVE)S, AND WHEN ARE
ALCOHOLS PRODUCED? 306 6.5.2 ACYLATION OF HYDRIDE DONORS: REDUCTION OF
CARBOXYLIC ACID DERIVATIVE 13.4 CONDENSATION OF ENOLATES WITH CARBONYL
COMPOUNDS: SYNTHESIS OF MICHAEL ACCEPTORS 565 13.4.1 ALDOL CONDENSATIONS
565 13.4.2 KNOEVENAGEL REACTION 571 13.5 ACYLATION OF ENOLATES 575
13.5.1 ACYLATION OF ESTER ENOLATES 575 13.5.2 ACYLATION OFKETONE
ENOLATES 579 13.5.3 ACYLATION OF THE ENOLATES OF ACTIVE-METHYLENE
COMPOUNDS 582 13.6 MICHAEL ADDITIONS OF ENOLATES 584 13.6.1 SIMPLE
MICHAEL ADDITIONS 584 13.6.2 TANDEM REACTIONS CONSISTING OF MICHAEL
ADDITION AND CONSECUTIVE REACTIONS 586 14 REARRANGEMENTS 595 14.1
NOMENCLATURE OF SIGMATROPIC SHIFTS 595 14.2 MOLECULAR ORIGINS FOR THE
OCCURRENCE OF [1,2]-REARRANGEMENTS 596 14.3 [1,2]-REARRANGEMENTS IN
SPECIES WITH AVALENCE ELECTRON SEXTET 598 14.3.1 [1,2]-REARRANGEMENTS OF
CARBENIUM IONS 598 14.3.2 [L,2]-REARRANGEMENTSINCARBENESORCARBENOIDS 615
14.4 [1,2]-REARRANGEMENTS WITHOUT THE OCCURRENCE OFA SEXTET
INTERMEDIATE. . . . 622 14.4.1 HYDROPEROXIDE REARRANGEMENTS 623 14.4.2
BAEYER-VILLIGER REARRANGEMENTS 624 14.4.3 OXIDATIONOFORGANOBORANE
COMPOUNDS 627 14.4.4 BECKMANN REARRANGEMENT 629 14.4.5 CURTIUS
DEGRADATION 630 14.5 CLAISEN REARRANGEMENT 632 14.5.1 CLASSICAL CLAISEN
REARRANGEMENT 632 14.5.2 IRELAND-CLAISEN REARRANGEMENTS 634 15 THERMAL
CYCLOADDITIONS 643 15.1 DRIVING FORCE AND FEASIBILITY OF ONE-STEP [4+2]-
AND [2+2]-CYCLOADDITIONS 643 15.2 TRANSITION STATE STRUCTURES OF
SELECTED ONE-STEP [4+2]- AND [2+2]-CYCLOADDITIONS 644 15.2. 15.3
DIELS-ALDER REACTIONS 654 15.3.1 STEREOSELECTIVITY OF DIELS-ALDER
REACTIONS 655 15.3.2 SUBSTITUENT EFFECTS ON REACTION RATES OF
DIELS-ALDER REACTIONS . . 661 15.3.3 REGIOSELECTIVITY OF DIELS-ALDER
REACTIONS 665 15.3.4 SIMPLE DIASTEREOSELECTIVITY OF DIELS-ALDER
REACTIONS 668 15.4 [2+2]-CYCLOADDITIONS WITH DICHLOROKETENE 671 15.5
1,3-DIPOLAR CYCLOADDITIONS 674 15.5.1 1,3-DIPOLES 674 15.5.2 FRONTIER
ORBITAL INTERACTIONS IN THE TRANSITION STATES OF ONE-STEP 1,3-DIPOLAR
CYCLOADDITIONS; SUSTMANN CLASSIFICATION 675 15.5.3 1,3-DIPOLAR
CYCLOADDITIONS OF DIAZOALKANES 677 15.5.4 1,3-DIPOLAR CYCLOADDITIONS
OFNITRILE OXIDES 680 15.5.5 1,3-DIPOLAR CYCLOADDITIONS AND 1,3-DIPOLAR
CYCLOREVERSIONS AS STEPS IN THE OZONOLYSIS OF ALKENES 683 15.5.6 A
TRICKY REACTION OF INORGANIC AZIDE 685 16 TRANSITION METAL-MEDIATED
ALKENYLATIONS, ARYLATIONS, AND ALKYNYLATIONS 691 16.1 ALKENYLATION AND
ARYLATION OF GILMAN CUPRATES 692 16.2 ARYLATION AND ALKYNYLATION OF
NEUTRAL ORGANOCOPPER COMPOUNDS 1 694 16.3 ALKENYLATION AND ARYLATION
OFGRIGNARD COMPOUNDS (KUMADA COUPLING) . . 701 16.4 PALLADIUM-CATALYZED
ALKENYLATIONS AND ARYLATIONS OF ORGANOMETALLIC COMPOUNDS 705 16.4.1 A
PRELUDE: PREPARATION OF HALOALKENES AND ALKENYLBORONIC ACID DERIVATIVES,
IMPORTANT BUILDING BLOCKS FOR PALLADIUM- MEDIATED C,C COUPLINGS;
CARBOCUPRATION OF ALKYNES 705 16.4.2 ALKENYLATION AND ARYLATION OF
BORON-BOUND GROUPS (SUZUKI COUPLING) 709 16.4. 17.4 REDUCTIONS 777
17.4.1 REDUCTIONS R SP3 *X- R SP3 *H OR R SP3 *X- R SP3 *M 778 17.4.2
ONE-ELECTRON REDUCTIONS OF CARBONYL COMPOUNDS AND ESTERS; REDUCTIVE
COUPLING 786 17.4.3 REDUCTIONS OF CARBOXYLIC ACID DERIVATIVES
TOALCOHOLSOR AMINES . . 795 17.4.4 REDUCTIONS OF CARBOXYLIC ACID
DERIVATIVES TO ALDEHYDES 800 17.4.5 REDUCTIONS OF CARBONYL COMPOUNDS TO
ALCOHOLS 800 17.4.6 REDUCTIONS OF CARBONYL COMPOUNDS TO HYDROCARBONS 800
17.4.7 HYDROGENATION OF ALKENES 806 17.4.8 REDUCTIONS OF AROMATIC
COMPOUNDS AND ALKYNES 815 17.4.9 THE REDUCTIVE STEP OF THE JULIA-LYTHGOE
OLEFINATION 819 SUBJECT INDEX 827
|
| any_adam_object | 1 |
| author | Brückner, Reinhard 1955- |
| author2 | Harmata, Michael 1959- |
| author2_role | edt |
| author2_variant | m h mh |
| author_GND | (DE-588)129496723 (DE-588)1035611589 |
| author_facet | Brückner, Reinhard 1955- Harmata, Michael 1959- |
| author_role | aut |
| author_sort | Brückner, Reinhard 1955- |
| author_variant | r b rb |
| building | Verbundindex |
| bvnumber | BV036090108 |
| callnumber-first | Q - Science |
| callnumber-label | QD262 |
| callnumber-raw | QD262 |
| callnumber-search | QD262 |
| callnumber-sort | QD 3262 |
| callnumber-subject | QD - Chemistry |
| classification_rvk | VK 6001 VK 6000 |
| classification_tum | CHE 608f |
| ctrlnum | (OCoLC)436031023 (DE-599)DNB995947813 |
| 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 Chemie |
| format | Book |
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| genre | (DE-588)4123623-3 Lehrbuch gnd-content |
| genre_facet | Lehrbuch |
| id | DE-604.BV036090108 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T22:11:20Z |
| institution | BVB |
| isbn | 9783642036507 |
| language | English German |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-018980723 |
| oclc_num | 436031023 |
| open_access_boolean | |
| owner | DE-29T DE-634 DE-83 DE-384 DE-91G DE-BY-TUM DE-11 |
| owner_facet | DE-29T DE-634 DE-83 DE-384 DE-91G DE-BY-TUM DE-11 |
| physical | xxxii, 855 Seiten Illustrationen (teilweise farbig) |
| publishDate | 2010 |
| publishDateSearch | 2010 |
| publishDateSort | 2010 |
| publisher | Springer |
| record_format | marc |
| spelling | Brückner, Reinhard 1955- Verfasser (DE-588)129496723 aut Organic Mechanisms reactions, stereochemistry and synthesis Reinhard Bruckner; edited by Michael Harmata; with foreword by Paul A. Wender Berlin ; Heidelberg Springer [2010] © 2010 xxxii, 855 Seiten Illustrationen (teilweise farbig) txt rdacontent n rdamedia nc rdacarrier Organic compounds Synthesis Reaktionsmechanismus (DE-588)4177123-0 gnd rswk-swf Organische Chemie (DE-588)4043793-0 gnd rswk-swf (DE-588)4123623-3 Lehrbuch gnd-content Organische Chemie (DE-588)4043793-0 s Reaktionsmechanismus (DE-588)4177123-0 s DE-604 Harmata, Michael 1959- (DE-588)1035611589 edt Wender, Paul A. wpr Erscheint auch als Online-Ausgabe 978-3-642-03651-4 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=018980723&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Brückner, Reinhard 1955- Organic Mechanisms reactions, stereochemistry and synthesis Organic compounds Synthesis Reaktionsmechanismus (DE-588)4177123-0 gnd Organische Chemie (DE-588)4043793-0 gnd |
| subject_GND | (DE-588)4177123-0 (DE-588)4043793-0 (DE-588)4123623-3 |
| title | Organic Mechanisms reactions, stereochemistry and synthesis |
| title_auth | Organic Mechanisms reactions, stereochemistry and synthesis |
| title_exact_search | Organic Mechanisms reactions, stereochemistry and synthesis |
| title_full | Organic Mechanisms reactions, stereochemistry and synthesis Reinhard Bruckner; edited by Michael Harmata; with foreword by Paul A. Wender |
| title_fullStr | Organic Mechanisms reactions, stereochemistry and synthesis Reinhard Bruckner; edited by Michael Harmata; with foreword by Paul A. Wender |
| title_full_unstemmed | Organic Mechanisms reactions, stereochemistry and synthesis Reinhard Bruckner; edited by Michael Harmata; with foreword by Paul A. Wender |
| title_short | Organic Mechanisms |
| title_sort | organic mechanisms reactions stereochemistry and synthesis |
| title_sub | reactions, stereochemistry and synthesis |
| topic | Organic compounds Synthesis Reaktionsmechanismus (DE-588)4177123-0 gnd Organische Chemie (DE-588)4043793-0 gnd |
| topic_facet | Organic compounds Synthesis Reaktionsmechanismus Organische Chemie Lehrbuch |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=018980723&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT brucknerreinhard organicmechanismsreactionsstereochemistryandsynthesis AT harmatamichael organicmechanismsreactionsstereochemistryandsynthesis AT wenderpaula organicmechanismsreactionsstereochemistryandsynthesis |