Ferrocene: a suitable framework for polymerization catalysis and frustrated Lewis pair chemistry
Gespeichert in:
| 1. Verfasser: | |
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| Format: | Abschlussarbeit Buch |
| Sprache: | English |
| Veröffentlicht: |
2013
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| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | V, 315 S. graph. Darst. 21 cm |
Internformat
MARC
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| 245 | 1 | 0 | |a Ferrocene |b a suitable framework for polymerization catalysis and frustrated Lewis pair chemistry |c vorgelegt von Xiaowu Wang |
| 264 | 1 | |c 2013 | |
| 300 | |a V, 315 S. |b graph. Darst. |c 21 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
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| 502 | |a Münster (Westfalen), Univ., Diss., 2013 | ||
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Datensatz im Suchindex
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| adam_text | TABLE OF CONTENTS
1 INTRODUCTION 1
1.1 POLYMERIZATION 1
1.2. AIM
OF THE POLYMERIZATION PROJECT 4
1.3 FRUSTRATED LEWIS PAIRS (FLP): THE BACKGROUND 7
1.4 FRUSTRATED LEWIS PAIRS PROJECT 12
2 THEORETICAL PART 16
2.1 POLYMERIZATION PROJECT 16
2.1.1 FEASIBILITY OF LIGAND SYNTHESIS 16
2.2.2 INTRODUCING BULKY
SUBSTITUENTS (-SIMEJ) AT A-POSITION ADJACENT
TO THE
-OH
GROUP 22
2.3 FRUSTRATED LEWIS PAIRS PROJECT 42
2.3.1. CHIRALITY IN FERROCENYL PHOSPHANES 42
2.3.2 SYNTHESIS OF PLANAR CHIRAL FERROCENE PHOSPHANE LIGANDS 43
2.4 HYDROBORATION REACTIONS OF COMPOUNDS (PS)-29, (/?S)-30 AND
(PS)-33 51
2.4.1 HYDROBORATION OF (PS)-2-(DIMESITYLPHOSPHANO)-L-VINYLFERROCENE
(/?S)-29 WITH
IIB(C*IV), 51
2.4.2 HYDROBORATION OF COMPOUND (PS)-30
WITH HB(C6F
5
)2 57
2.5 DIHYDROGEN SPLITTING WITH COMPOUND
(PS)-35 AND COMPOUNDS
44A
AND 44B 59
2.5.1 DIHYDROGEN SPLITTING WITH
COMPOUND (PS)-35 59
2.5.2 DIHYDROGEN SPLITTING WITH COMPOUNDS 44A
AND 44B 62
2.6 REACTIONS BETWEEN COMPOUND
[JJS)-35
WITH SMALL MOLECULES 63
2.6.1 REACTION OF COMPOUND (PS)-35
WITH
P-TOLYL ACETYLENE 65
2.6.2 REACTION OF COMPOUND (PS)-35
WITH 1-PENTYNE 66
2.6.3 REACTION OF COMPOUND (PS)-35 WITH
2-METHYL-1,3-BUTENYRIE 67
2.7 REACTIONS OF THE BORANE LEWIS CENTER
WITH LEWIS BASES 68
2.8 REACTION OF COMPOUND (/?S)-35 WITH
NO 71
2.9 CATALYTIC HYDROGENATION OF IMINES, ENAMINES, UNFUNCTONALIZED OLEFINS
BY
COMPOUND (PS)-35 74
2.9.1 ASYMMETRIC HYDROGENATION OF A -TERTBUTYLBENZALDIMINE USING
COMPOUND
(/ S)-35 76
2.9.2 FURTHER CHARACTERIZATION OF THE OBTAINED AMINE,
EE DETERMINATION 77
2.9.3 HYDROGENATION OF (L-PHENYLETHYLIDENE)(2-TOLYL)AMINE USING
COMPOUND (PS)-
35 78
2.9.4 ASYMMETRIC HYDROGENATION OF /V-(1-PHENYLETHYLIDENE)ANILINE USING
COMPOUND (/?S)-35 78
2.9.5 HYDROGENATION OF YV,/V-DIETHYL-/V-(L-PHENYLETHENYL)AMINE USING
COMPOUND
(/ S)-35 79
2.9.6 HYDROGENATION OF 1-(4-MORPHOLINO)CYCLOHEXENE USING COMPOUND
(PS)-35 . 79
2.9.7 HYDROGENATION OF VINYLFERROCENE BY COMPOUND (PS)-35 80
2.9.8 HYDROGENATION OF 2-PROPENYLFERROCENE BY COMPOUND
(PS)-35 81
2.9.9 HYDROGENATION OF VINYLFERROCENE BY COMPOUND
D
82
2.9.10 HYDROGENATION OF 2-PROPENYLFERROCENE BY COMPOUND
D
82
3 A TETRAMETHYLENE BRIDGED P/B
SYSTEM 84
3.1 SYNTHESIS OF BUT-3-ENYLDIMESITYLPHOSPHAN 46 85
3.2 SYNTHESIS OF THE SIX-MEMBERED P/B SYSTEM 47 86
I
HTTP://D-NB.INFO/1037809416
3.3 DIHYDROGEN ACTIVATION BY COMPOUND 47 89
3.4 REACTION BETWEEN SMALL MOLECULES AND COMPOUND
47 92
3.4.1 REACTION BETWEENP-TOLYL ACETYLENE
AND COMPOUND
47 92
3.4.2 REACTION BETWEEN NO AND COMPOUND
47 93
3.5 CATALYTIC HYDROGENATION OF IMINES, ENANMINES, UNFUNCTIONALIZED
OLEFINS USING
47
94
3.5.1 CATALYTIC HYDROGENATION OF IMINES USING
47 94
3.5.2 CATALYTIC HYDROGENATION OF ENAMINES USING
47 95
3.5.3 CATALYTIC HYDROGENATION OF UNFUNCTIONALIZED OLEFINS
USING 47 95
4 SUMMARY 97
4.1 SYNTHESIS OF [FE-SALIMINE] LIGANDS AND THEIR ZR COMPLEXES FOR ETHENE
POLYMERIZATION 97
4.2 PLANAR CHIRAL ALKENYL SUBSTITUTED FERROCENYL PHOSPHANE LIGANDS
AND THEIR
POTENTIAL APPLICATION IN FLP CHEMISTRY 100
4.3 STUDY ON A TETRAMETHYLENE BRIDGED P/B FLP SYSTEM AND
ITS REACTIVITIES 103
5. EXPERIMENTAL PART 105
5.1 GENERAL REMARKS 105
5.1.1 TECHNIQUES 105
5.1.2 SOLVENTS 105
5.1.3 REAGENTS 105
5.1.4 FLASH CHROMATOGRAPHY 105
5.2 ANALYTICAL METHODS 106
5.2.1. POLARIMETRY 106
5.2.2 POLYMER ANALYSIS 106
5.2.3 MELTING POINTS 106
5.2.4 ELEMENTAL ANALYSIS 106
5.2.5 INFRARED SPECTROSCOPY 107
5.2.6 MASS SPECTROMETRY 107
5.2.7 HIGH PERFORMANCE LIQUID CHROMATOGRAPHY (HPLC) 107
5.2.8 NMR
SPECTROSCOPY 107
5.2.9 X-RAY SINGLE CRYSTAL STRUCTURE ANALYSIS 109
5.2.10 LITERATURE SEARCH 109
5.3 SYNTHESIS OF PRECURSORS 109
5.3.1 L-DIMETHYL MALIC ACID ESTER(L) 109
5.3.2 (S)-1,2,4-BUTANETRIOL (2) 110
5.3.3 FERROCENE CARBALDEHYDE DIMETHYL ACETAL (3) 111
5.3.4 (S,S)-(4-HYDROXYMETHYL-L,3-DIOXAN-2-YL)FERROCENE ((S,S)-4) 111
5.3.5 (-)-(S,S)- (4-METHOXYMETHYL-L,3-DIOXAN-2-YL)FERROCENE ((S,S)-5)
112
5.3.6
(-)-(S,S,PS)-2-(4-METHOXYMETHYL-L,3-DIOXAN-2-YL)-L-TRIMETHYLSILYL-FERROCENE
L(S.S./ S)-6) 113
5.3.7
(+)-(S,S,/?R)-L-IODO-2-(4-METHOXYMETHYL-L,3-DIOXAN-2-Y[)-3-TRIMETHYLSILYL-
FERROCENE ((S,S,PR)-7) 114
5.3.8 (S,S,PR)-1,1 -DIIODO-2-(4-METHOXYMETHYL-1,3-DIOXAN-2-YL)-3-
TRIMETHYLSILYLFERROCENE 115
5.3.9 PREPARATION OF COMPOUND (S,S,/;S)-9 116
5.3.10 PREPARATION OF COMPOUND (S,S,PS)-10 118
II
5.3.11 PREPARATION OF COMPOUND
(/JS)-
11
120
5.3.12 PREPARATION OFCOMPOUND (/?S)-12A 121
5.3.13 PREPARATION OFCOMPOUND (/?S)-I3A 123
5.3.14 PREPARATION OF COMPOUND (PS)-12B 125
5.3.15 PREPARATION OFCOMPOUND (/?S)-13B 127
5.3.16 PREPARATION OFCOMPOUND (PS)-I2C 128
5.3.17 PREPARATION OFCOMPOUND (PS)-13C 130
5.3.18 PREPARATION OFCOMPOUND
(PS,PS)-14A 132
5.3.19 PREPARATION OF COMPOUND (PS,PS)-14B 133
5.3.20 PREPARATION OFCOMPOUND
(/^S,/;S)-14C 135
5.3.21 PREPARATION OF COMPOUND (S,S,/;S)-15 136
5.3.22 PREPARATION OFCOMPOUND 16 138
5.3.23 PREPARATION OFCOMPOUND (S,S,/ R)-17 140
5.3.24 PREPARATION OFCOMPOUND
(S,S,PS)-18 142
5.3.25 PREPARATION OFCOMPOUND (PSJ-19 144
5.3.26 PREPARATION OFCOMPOUND (/)S)-20 146
5.3.27 PREPARATION OFCOMPOUND
(/?S)-21A 148
5.3.28 PREPARATION OFCOMPOUND (/?S)-21B 149
5.3.29 PREPARATION OFCOMPOUND (PS)-21C 151
5.3.30 PREPARATION OFCOMPOUND
(PS)-21D 153
5.3.31 PREPARATION OF COMPOUND (PS,PS)-22A 154
5.3.32 PREPARATION OFCOMPOUND (PS,/?S)-22D 156
5.3.33 PREPARATION OFCOMPOUND (YYR)-23 158
5.3.34 PREPARATION OFCOMPOUND
(S,S,/?S)-24 159
5.3.35 PREPARATION OFCOMPOUND (PS)-25 162
5.3.36 PREPARATION OF COMPOUND {PS)-26 163
5.4 SYNTHESIS OF KETIMINES 165
5.4.1 SYNTHESIS OF /V-TERTBUTYLBENZALDIMINE 165
5.4.2 SYNTHESIS OF (L-PHENYLETHYLIDENE)(2-TOLYL)AMINE 165
5.4.3 SYNTHESIS OF /V-(1-PHENYLETHYLIDENE)ANILINE 166
5.5 SYNTHESIS OF OTHER ORGANIC SUBSTRATES 167
5.5.1 SYNTHEIS OF CHLORODIMESITYLPHOSPHINE 167
5.5.2 PREPARATION OF VINYLFERROCENE 167
5.5.3 PREPARATION OF 2-PROPENYLFERROCENE 168
5.6 SYNTHSIS OF ORGANOBORANE PRECURSORS 169
5.6.1 SYNTHEIS OF TRIS(PENTAFLUOROPHENYL)BORANE 169
5.6.2 SYNTHESIS OF BIS(PENTAFLUOROPHENYL)BORANE 170
5.6.3 SYNTHESIS OF (C
6
F
5
)
2
BOET 171
5.7 SYNTHESIS OF PLANAR CHIRAL FERROCENYL PHOSPHANE LIGANDS 171
5.7.1 (S,S,
J
OS)-2-(4-METHOXYMETHYL-1,3-DIOXAN-2-YL)-1 -
DIMESITYLPHOSPHANOFERROCENE (S,S,PS)-27 171
5.7.2 L-DIMESITYLPHOSPHANOFERROCENE-2-CARBALDEHYDE (PS)-2S 175
5.7.3 L-DIMESITYLPHOSPHANO-2-VINYLFERROCENE (/ S)-29 178
5.7.4 L-DIMESITYLPHOSPHANO-2-(2-PHENYLETHEN-L-YL)FERROCENE (/?S)-30 180
5.7.5 L-DIPHENYLPHOSPHANO-(S,S,/; S)-2-(4-NIETHOXYMETHYL-L,3-DIOXAN-2-
YL)FERROCENE (S,S,/?S)-31 183
III
5.7.6 L-DIPHENYLPHOSPLIANOFERROCENC-2-CARBALDEHYDE (J S)-32 184
5.7.7 2-VINYL-L-DIPHENYLPHOSPHANOFERROEENE (/;S)-33 185
5.7.8 PREPARATION OFCOMPOUND (PS)-34 186
5.7.9 PREPARATION OF COMPOUND (PS)-35 188
5.7.10 PREPARATION OFCOMPOUND
(PS)-36 192
5.7.11 PREPARATION OFCOMPOUND
(/?S)-37 196
5.7.12 PREPARATION OF COMPOUND (PS)-38 197
5.7.13 PREPARATION OF COMPOUND (PS)-39 201
5.7.14 PREPARATION OF COMPOUND (/ S)-40 205
5.7.15 PREPARATION OF COMPOUND (/ S)-41 208
5.7.16 PREPARATION OFCOMPOUND (/;S)-42 212
5.7.17 PREPARATION OF COMPOUND (PS)-43 215
5.8 SYNTHESIS AND REACTIVITY OF TETRAMETHYLENE BRIDGED P/B SYSTEM 219
5.8.1 BUT-3-ENYLDIMESITYLPHOSPHAN 46 219
5.8.2 PREPARATION OF COMPOUND 47 221
5.8.3PREPARATION OFCOMPOUND 48 224
5.8.4 PREPARATION OF COMPOUND 49 226
5.8.5 PREPARATION OFCOMPOUND 50 228
5.8.6 PREPARATION OF COMPOUD 51 230
5.8.7 PREPARATION OF COMPOUND 52 231
5.8.8 PREPARATION OFCOMPOUND 53 232
5.8.9 SPLITTING TEST OFCOMPOUND
53 232
5.9 GENERAL PROCEDURES FOR
THE HYDROGENATION OF IMINES 233
5.9.1 HYDROGENATION OF /V-TERTBUTYLBENZALDIMINE 234
5.9.2 FURTHER CHARACTERIZATION OF THE OBTAINED
AMINE, EE DETERMINATION 235
5.9.3 HYDROGENATION OF N-(1-PHENYLETHYLIDENE)ANILINE 239
5.9.4 HYDROGENATION OF (L-PHENYLETHYLIDENE)(2-TOLY!)AMINE 241
5.10 GENERAL PROCEDURES FOR THE HYDROGENATION
OF ENAMINES 243
5.10.1 HYDROGENATION OF A ,A -DIETHYL-/V-(
1 -PHENYLETHENYL)AMINE 244
5.10.2 HYDROGENATION OF L-(4-MORPHOLINO)CYCLOHEXENE 245
5.11 GENERAL PROCEDURES FOR THE HYDROGENATION OF FERROCENEALKENE 247
5.11.1 HYDROGENATION OF VINYLFERROCENE 247
5.11.2 HYDROGENATION OF 2-PROPENYLFERROCENE BY (PS)-35 248
5.12 HYDROGENATION OF FERROCENE ALKENE BY ETHYLENE BRIDGED P/B SYSTEM
250
5.12.1 HYDROGENATION OF VINYLFERROCENE BY ETHYLENE BRIDGED P/B SYSTEM
250
5.12.2 HYDROGENATION OF 2-PROPENYLFERROCENE BY ETHYLENE BRIDGED P/B
SYSTEM . 250
5.13 HYDROGENATION OF IMINES BY TETRAMETHYLENE BRIDGED P/B SYSTEM 47 251
5.13.1 HYDROGENATION OF A -TERTBUTYLBENZALDIMINE BY TETRAMETHYLENE
BRIDGED P/B
SYSTEM 47 252
5.13.2 HYDROGENATION OF (L-PHENYLETHYLIDENE)(2-TOLYL)AMINE BY
TETRAMETHYLENE
BRIDGED P/B SYSTEM 47 252
5.14 HYDROGENATION OF ENAMINES BY TETRAMETHYLENE BRIDGED P/B SYSTEM 47
253
5.14.1 HYDROGENATION OF AYV-DIETHYL-/V-(L-PHENYLETHENYL)AMINE
TETRAMETHYLENE
BRIDGED P/B SYSTEM 47 253
5.14.2 HYDROGENATION OF L-(4-MORPHOLINO)CYCLOHEXENE BY TETRAMETHYLENE
BRIDGED
P/B SYSTEM 47 254
IV
5.15 HYDROGENATION OF FERROCENE ALKENE BY TETRAMETHYLENE BRIDGED P/B
SYSTEM 47
254
6 APENDIX 256
6.1 SYMBOL ABBREVIATIONS 256
6.2 NMR
SPECTRA OF SELECTED COMPOUNDS 257
6.3 X-RAY CRYSTAL STRUCTURE ANALYSIS 290
V
|
| any_adam_object | 1 |
| author | Wang, Xiaowu 1984- |
| author_GND | (DE-588)1036755673 |
| author_facet | Wang, Xiaowu 1984- |
| author_role | aut |
| author_sort | Wang, Xiaowu 1984- |
| author_variant | x w xw |
| building | Verbundindex |
| bvnumber | BV041397446 |
| ctrlnum | (OCoLC)861224168 (DE-599)DNB1037809416 |
| dewey-full | 547.05621 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.05621 |
| dewey-search | 547.05621 |
| dewey-sort | 3547.05621 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
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| genre_facet | Hochschulschrift |
| id | DE-604.BV041397446 |
| illustrated | Illustrated |
| indexdate | 2024-07-10T00:55:49Z |
| institution | BVB |
| language | English |
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| physical | V, 315 S. graph. Darst. 21 cm |
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| spelling | Wang, Xiaowu 1984- Verfasser (DE-588)1036755673 aut Ferrocene a suitable framework for polymerization catalysis and frustrated Lewis pair chemistry vorgelegt von Xiaowu Wang 2013 V, 315 S. graph. Darst. 21 cm txt rdacontent n rdamedia nc rdacarrier Münster (Westfalen), Univ., Diss., 2013 (DE-588)4113937-9 Hochschulschrift gnd-content DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=026845076&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Wang, Xiaowu 1984- Ferrocene a suitable framework for polymerization catalysis and frustrated Lewis pair chemistry |
| subject_GND | (DE-588)4113937-9 |
| title | Ferrocene a suitable framework for polymerization catalysis and frustrated Lewis pair chemistry |
| title_auth | Ferrocene a suitable framework for polymerization catalysis and frustrated Lewis pair chemistry |
| title_exact_search | Ferrocene a suitable framework for polymerization catalysis and frustrated Lewis pair chemistry |
| title_full | Ferrocene a suitable framework for polymerization catalysis and frustrated Lewis pair chemistry vorgelegt von Xiaowu Wang |
| title_fullStr | Ferrocene a suitable framework for polymerization catalysis and frustrated Lewis pair chemistry vorgelegt von Xiaowu Wang |
| title_full_unstemmed | Ferrocene a suitable framework for polymerization catalysis and frustrated Lewis pair chemistry vorgelegt von Xiaowu Wang |
| title_short | Ferrocene |
| title_sort | ferrocene a suitable framework for polymerization catalysis and frustrated lewis pair chemistry |
| title_sub | a suitable framework for polymerization catalysis and frustrated Lewis pair chemistry |
| topic_facet | Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=026845076&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT wangxiaowu ferroceneasuitableframeworkforpolymerizationcatalysisandfrustratedlewispairchemistry |