Stereochemistry, mechanism and Silicon: An introd. to the dynamic stereochemistry and reaction mechanisms of Silicon centers
Gespeichert in:
| Beteilige Person: | |
|---|---|
| Format: | Buch |
| Sprache: | Englisch |
| Veröffentlicht: |
New York
McGraw-Hill
1965
|
| Schriftenreihe: | McGraw-Hill series in advanced chemistry.
|
| Schlagwörter: | |
| Links: | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=001488939&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| Umfang: | XVI, 189 S. graph. Darst. |
Internformat
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| 100 | 1 | |a Sommer, Leo Hans-Jürgen |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Stereochemistry, mechanism and Silicon |b An introd. to the dynamic stereochemistry and reaction mechanisms of Silicon centers |
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Datensatz im Suchindex
| DE-BY-TUM_call_number | 0302 CHE 634f 1965 A 5920 |
|---|---|
| DE-BY-TUM_katkey | 367501 |
| DE-BY-TUM_location | 03 |
| DE-BY-TUM_media_number | 040030044412 |
| _version_ | 1821937873461444609 |
| adam_text | Stereochemistry,
Mechanism
and Silicon
An Introduction to the
Dynamic Stereochemistry
and Reaction Mechanisms
of Silicon Centers
Contents
Preface
one Fundamental considerations
1-1 Introduction 2
1-2 sp3 o-Bonding and tetrahedral geometry 2
1-3 w-Bonding 3
1-4 The 3d orbitals 4
1-5 o-Bonding and the 3d orbitals 5
1-6 Bond energy, bond refraction, and bond polarity 24
1-7 Siliconium ions 28
1-8 Organosilyl free radicals and silanions 37
xiii
Xiv Contents
two Optically active compounds 39
2-1 Synthesis of optically active a-NpPhMeSiX compounds (R3Si*X) 40
2-2 Assignment of relative configuration 43
2-3 Special need for stereochemical studies of compounds
of second-row elements 43
three Stereochemistry and mechanisms of silicon-oxygen
bonds 47
3-1 Introduction 48
3-2 Syntheses 48
3-3 Grignard reduction of R3Si*OMe: a four-center retention mechanism 49
3-4 Retention reactions of R3Si*0R and R3Si*0Si*R3 51
3-5 Mechanisms of R3Si*OR compounds: discussion of SNi-Si
and SN2-Si mechanisms 56
3-6 Inversion reactions of R3Si*0C0R 66
3-7 An inversion reaction for R3Si*OTs 70
3-8 Mechanism SN2-Si for R3Si*0C0R 72
3-9 Summary of stereochemistry and mechanisms for R3Si*—0—
compounds 73
four Stereochemistry and mechanism: of silicon-halogen
bonds 75
4-1 Introduction 76
4-2 Inversion: a common stereochemical path for R3Si*CI and R3Si*Br 78
4-3 Solvent-induced racemization of R3Si*CI: evidence for an ionization
mechanism 84
4-4 Inversion and retention reactions of R3Si*F 87
4-5 Racemization of R3Si*F without displacement of fluoride ion:
expanded-octet (EO) return 88
4-6 Mechanisms of R3Si*Hal compounds: discussion of SN2-Si, SN1-Si,
SN2*-Si, and SNi-Si mechanisms 91
Contents XV
4-7 Summary of stereochemistry and mechanisms for R3Si*Hal
compounds 93
five Halide-halide exchange at asymmetric silicon:
SN2-Si and SN1-Si Mechanisms 95
5-1 Introduction 96
5-2 Halide-halide exchange by mechanism SN2-Si 96
5-3 Racemization of R3Si*CI by cyclohexylammonium salts 97
5-4 Chloride-chloride exchange at asymmetric silicon 98
six Stereochemistry and mechanisms of R3Si*H 101
6-1 Introduction 102
6-2 Deuterium-hydrogen exchange with retention of configuration 102
6-3 Retention reactions of R3Si*H with oxygen-containing bases 104
6-4 Retention reactions of R3Si*H with chlorine and bromine 107
6-5 A retention reaction of R3Si*H with perbenzoic acid 110
6-6 Summary of stereochemistry and mechanisms of R3Si*H 110
seven Relative and absolute configurations of
a-maphthyipl enylmethylsilanes 113
7-1 Introduction 114
7-2 Chemical correlations of configuration
7-3 X-ray application of the Fredga method
7-4 Optical rotatory dispersion 121 l
7-5 Absolute configurations 123
eight
Strut ture and reactivity 125
8-1 Introduction 126
8-2 Polar and steric effects of substituents 127
xvi Contents
8-3 Effects of the leaving group and the reagent 146
8-4 Effects of the solvent 150
nine Bridgehead silicon 153
9-1 Introduction 154
9-2 Bridgehead silicon chlorides 154
9-3 Bridgehead silicon hydrides 156
9-4 Chloride-chloride exchange at bridgehead silicon 158
ten Recent advances 161
10-1 New optically active systems 162
10-2 Coupling reactions with organometailic reagents: significance
for mechanism 166
eleven A general survey of the stereoc! emistry
and mechanisms of silicon centers 173
11-1 Introduction 174
11-2 Reaction profiles for SN2-Si and SNi-Si mechanisms 174
11-3 The SN2-Si mechanism 175
11-4 The SNi-Si mechanism 176
11-5 The SN1-Si ionization mechanism 178
11-6 The SN2*-Si mechanism 179
11-7 The SN2**-Si mechanism 180
11-8 The principle of least motion of nonreacting groups 182
11-9 The SN2-Si stereochemistry rule and participation
of the Id,,* orbital 184
Index of reactions 187
|
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| id | DE-604.BV002265817 |
| illustrated | Illustrated |
| indexdate | 2024-12-20T07:48:34Z |
| institution | BVB |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-001488939 |
| oclc_num | 630339744 |
| open_access_boolean | |
| owner | DE-91G DE-BY-TUM DE-355 DE-BY-UBR DE-19 DE-BY-UBM DE-83 DE-11 DE-188 |
| owner_facet | DE-91G DE-BY-TUM DE-355 DE-BY-UBR DE-19 DE-BY-UBM DE-83 DE-11 DE-188 |
| physical | XVI, 189 S. graph. Darst. |
| psigel | TUB-nveb |
| publishDate | 1965 |
| publishDateSearch | 1965 |
| publishDateSort | 1965 |
| publisher | McGraw-Hill |
| record_format | marc |
| series2 | McGraw-Hill series in advanced chemistry. |
| spellingShingle | Sommer, Leo Hans-Jürgen Stereochemistry, mechanism and Silicon An introd. to the dynamic stereochemistry and reaction mechanisms of Silicon centers Stereochemie (DE-588)4129569-9 gnd Reaktionsmechanismus (DE-588)4177123-0 gnd Siliciumorganische Verbindungen (DE-588)4077449-1 gnd |
| subject_GND | (DE-588)4129569-9 (DE-588)4177123-0 (DE-588)4077449-1 |
| title | Stereochemistry, mechanism and Silicon An introd. to the dynamic stereochemistry and reaction mechanisms of Silicon centers |
| title_auth | Stereochemistry, mechanism and Silicon An introd. to the dynamic stereochemistry and reaction mechanisms of Silicon centers |
| title_exact_search | Stereochemistry, mechanism and Silicon An introd. to the dynamic stereochemistry and reaction mechanisms of Silicon centers |
| title_full | Stereochemistry, mechanism and Silicon An introd. to the dynamic stereochemistry and reaction mechanisms of Silicon centers |
| title_fullStr | Stereochemistry, mechanism and Silicon An introd. to the dynamic stereochemistry and reaction mechanisms of Silicon centers |
| title_full_unstemmed | Stereochemistry, mechanism and Silicon An introd. to the dynamic stereochemistry and reaction mechanisms of Silicon centers |
| title_short | Stereochemistry, mechanism and Silicon |
| title_sort | stereochemistry mechanism and silicon an introd to the dynamic stereochemistry and reaction mechanisms of silicon centers |
| title_sub | An introd. to the dynamic stereochemistry and reaction mechanisms of Silicon centers |
| topic | Stereochemie (DE-588)4129569-9 gnd Reaktionsmechanismus (DE-588)4177123-0 gnd Siliciumorganische Verbindungen (DE-588)4077449-1 gnd |
| topic_facet | Stereochemie Reaktionsmechanismus Siliciumorganische Verbindungen |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=001488939&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT sommerleohansjurgen stereochemistrymechanismandsiliconanintrodtothedynamicstereochemistryandreactionmechanismsofsiliconcenters |
Inhaltsverzeichnis
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Teilbibliothek Chemie
| Signatur: |
0302 CHE 634f 1965 A 5920
Lageplan |
|---|---|
| Exemplar 1 | Ausleihbar Am Standort |