Titanium and zirconium in organic synthesis:
Gespeichert in:
| Format: | Buch |
|---|---|
| Sprache: | English |
| Veröffentlicht: |
Weinheim
WILEY-VCH
2002
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XXV, 512 S. Ill. : 24 cm |
| ISBN: | 3527304282 |
Internformat
MARC
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| 245 | 1 | 0 | |a Titanium and zirconium in organic synthesis |c ed. by Ilan Marek |
| 264 | 1 | |a Weinheim |b WILEY-VCH |c 2002 | |
| 300 | |a XXV, 512 S. |b Ill. : 24 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 4 | |a Composés organiques - Synthèse | |
| 650 | 4 | |a Composés organiques titanés | |
| 650 | 4 | |a Composés organiques zirconiés | |
| 650 | 4 | |a Organic compounds |x Synthesis | |
| 650 | 4 | |a Organotitanium compounds | |
| 650 | 4 | |a Organozirconium compounds | |
| 650 | 0 | 7 | |a Organische Synthese |0 (DE-588)4075695-6 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Zirkoniumverbindungen |0 (DE-588)4190957-4 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Titanorganische Verbindungen |0 (DE-588)4043813-2 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Titanverbindungen |0 (DE-588)4185575-9 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Zirkoniumorganische Verbindungen |0 (DE-588)4190954-9 |2 gnd |9 rswk-swf |
| 689 | 0 | 0 | |a Organische Synthese |0 (DE-588)4075695-6 |D s |
| 689 | 0 | 1 | |a Zirkoniumorganische Verbindungen |0 (DE-588)4190954-9 |D s |
| 689 | 0 | |5 DE-604 | |
| 689 | 1 | 0 | |a Organische Synthese |0 (DE-588)4075695-6 |D s |
| 689 | 1 | 1 | |a Titanorganische Verbindungen |0 (DE-588)4043813-2 |D s |
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| 689 | 2 | 1 | |a Titanverbindungen |0 (DE-588)4185575-9 |D s |
| 689 | 2 | |5 DE-604 | |
| 689 | 3 | 0 | |a Organische Synthese |0 (DE-588)4075695-6 |D s |
| 689 | 3 | 1 | |a Zirkoniumverbindungen |0 (DE-588)4190957-4 |D s |
| 689 | 3 | |5 DE-604 | |
| 700 | 1 | |a Marek, Ilan |e Sonstige |4 oth | |
| 856 | 4 | 2 | |m DNB Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009793068&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
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Datensatz im Suchindex
| _version_ | 1808045645105201152 |
|---|---|
| adam_text |
CONTENTS
FOREWORD
V
PREFACE
XXI
LIST
OF
CONTRIBUTORS
XXIII
1
SYNTHESIS
AND
REACTIVITY
OF
ZIRCONOCENE
DERIVATIVES
1
EI-ICHI
NEGISHI
AND
SHOUQUAN
HUO
1.1
1.2
INTRODUCTION
AND
HISTORICAL
BACKGROUND
1
FUNDAMENTAL
PATTERNS
OF
TRANSFORMATIONS
OF
ZIRCONOCENE
DERIVATIVES
3
1.3
1.3.1
1.3.2
1.3.3
1.3.4
1.4
1.4.1
SYNTHESIS
OF
ORGANIC
DERIVATIVES
OF
ZRCP
2
8
TRANSMETALLATION
8
HYDROZIRCONATION
10
OXIDATIVE
ADDITION
11
N-COMPLEXATION
(OXIDATIVE
N-COMPLEXATION)
12
REACTIVITY
OF
ORGANYLZIRCONOCENE
COMPOUNDS
14
FORMATION
OF
CARBON
-
HYDROGEN
AND
CARBON
-
HETEROATOM
BONDS
15
1.4.1.1
1.4.1.2
1.4.1.3
1.4.2
1.4.3
1.4.3.1
1.4.3.2
1.4.3.3
1.4.4
1.4.5
PROTONOLYSIS
AND
DEUTEROLYSIS
15
HALOGENOLYSIS
15
OXIDATION
16
FORMATION
OF
CARBON
-
METAL
BONDS
BY
TRANSMETALLATION
16
FORMATION
OF
CARBON
-
CARBON
BONDS
18
POLAR
CARBON
-
CARBON
BOND-FORMING
REACTIONS
18
CARBONYLATION
AND
OTHER
MIGRATORY
INSERTION
REACTIONS
23
CARBOZIRCONATION
AND
RELATED
CARBOMETALLATION
REACTIONS
26
O-BOND
METATHESIS
OF
ZIRCONACYCLES
40
IONIC
REACTIONS
OF
ORGANOZIRCONATES
44
REFERENCES
45
XIII
CONTENTS
2
ZIRCONACYDOPENTADIENES
IN
ORGANIC
SYNTHESIS
50
TAMOTSU
TAKAHASHI
AND
YANZHONG
LI
2.1
2.2
2.2.1
2.2.2
2.2.3
2.2.4
2.3
2.3.1
2.3.1.1
2.3.1.2
2.3.1.3
2.3.1.4
2.3.1.5
2.3.1.6
2.3.2
2.3.2.1
2.3.2.2
2.3.2.3
2.3.2.4
2.3.2.5
2.3.2.6
2.3.3
2.3.3.1
2.3.3.2
INTRODUCTION
50
PREPARATION
AND
REACTION
OF
ZIRCONACYDOPENTADIENES
50
PREPARATION
OF
ZIRCONACYDOPENTADIENES
50
HYDROLYSIS
53
HALOGENOLYSIS
55
FORMATION
OF
HETEROCYDES
BY
SUBSTITUTION
REACTIONS
57
CARBON
-
CARBON
BOND
FORMATION
59
TRANSMETALATION
59
TRANSMETALATION
TO
COPPER
59
TRANSMETALATION
TO
NICKEL
60
TRANSMETALATION
TO
LITHIUM
60
TRANSMETALATION
TO
ZINC
61
TRANSMETALATION
TO
ALUMINUM
61
TRANSMETALATION
TO
OTHER
METALS
62
COUPLING
REACTIONS
62
COUPLING
WITH
ALLYL
HALIDES
62
COUPLING
WITH
BENZYL
HALIDES
63
COUPLING
WITH
ALKYNYL
HALIDES
63
COUPLING
WITH
ALKENYL
HALIDES
65
COUPLING
WITH
ARYL
HALIDES
66
COMBINATION
OF
COUPLING
REACTIONS
66
ADDITION
REACTIONS
TO
CARBON
-
CARBON
TRIPLE
BONDS
67
1,1
-ADDITION
TO
CARBON
-
CARBON
TRIPLE
BONDS
68
1,2
-ADDITION
TO
CARBON-CARBON
TRIPLE
BONDS:
FORMATION
OF
BENZENE
DERIVATIVES
68
2.3.3.3
2.3.3.4
2.3.3.5
BENZENE
FORMATION
FROM
THREE
DIFFERENT
ALKYNES
70
APPLICATIONS
OF
BENZENE
FORMATION
72
ADDITION
OF
AZAZIRCONACYCLOPENTADIENES
TO
CARBON-CARBON
TRIPLE
BONDS
74
2.3.3.6
2.3.4
2.3.5
2.3.6
2.3.6.1
2.3.6.2
2.3.7
2.4
ADDITION
TO
CARBON
-
CARBON
DOUBLE
BONDS
75
INSERTION
REACTIONS
OF
CARBON
MONOXIDE
AND
ISONITRILES
76
CARBON
-
CARBON
BOND
CLEAVAGE
REACTIONS
77
ELIMINATION
REACTIONS
79
ELIMINATION
OF
AN
ALKOXY
GROUP
OR
HALOGEN
79
REDUCTIVE
ELIMINATION
80
REARRANGEMENT
81
CONCLUSION
82
REFERENCES
83
CONTENTS
|
XIII
3
ELABORATION
OF
ORGANOZIRCONIUM
SPECIES
BY
INSERTION
OF
CARBENOIDS
86
SALLY
DIXON
AND
RICHARD
J.
WHITBY
3.1
INTRODUCTION
86
3.1.1
FORMATION
OF
ZIRCONACYCLES
87
3.2
CARBONYLATION
AND
ISONITRILE
INSERTION
88
3.2.1
ACYCLIC
ORGANOZIRCONOCENES
88
3.2.2
ZIRCONACYCLES
89
3.3
INSERTION
OF
1-HALO-L-LITHIO
SPECIES
INTO
ORGANOZIRCONOCENES
90
3.3.1
INSERTION
OF
1-HALO-L-LITHIOALKENES
INTO
ACYCLIC
ORGANOZIRCONOCENE
CHLORIDES
91
3.3.1.1
INSERTION
OF
L-CHLORO-L-LITHIO-2,
2
-DISUBSTITUTED
ALKENES
91
3.3.1.2
INSERTION
OF
L-CHLORO-L-LITHIO-2-MONOSUBSTITUTED
ALKENES
92
3.3.1.3
FURTHER
ELABORATION
OF
CARBENOID
INSERTION
PRODUCTS
93
3.3.1.4
INSERTION
OF
L-LITHIO-L,2-DIHALOALKENES
INTO
ACYCLIC
ORGANOZIRCONOCENE
CHLORIDES
93
3.3.1.5
INSERTION
OF
1-HALO-L-LITHIOALKENES
INTO
ZIRCONACYCLES
94
3.3.2
INSERTION
OF
ALLENYL
CARBENOIDS
94
3.3.2.1
INSERTIONS
INTO
ACYCLIC
ORGANOZIRCONOCENE
CHLORIDES
94
3.3.2.2
INSERTIONS
INTO
ZIRCONACYCLES
95
3.3.3
INSERTION
OF
ALLYL
CARBENOIDS
INTO
ORGANOZIRCONIUM
SPECIES
96
3.3.3.1
INSERTION
INTO
ACYCLIC
ORGANOZIRCONOCENE
CHLORIDES
96
3.3.3.2
INSERTIONS
INTO
ZIRCONACYCLES
96
3.3.4
INSERTION
OF
PROPARGYL
CARBENOIDS
INTO
ZIRCONACYCLES
98
3.3.5
INSERTION
OF
A-SUBSTITUTED
ALKYL
CARBENOIDS
98
3.3.5.1
INSERTIONS
INTO
ACYCLIC
ALKENYLZIRCONOCENE
CHLORIDES.
A
CONVERGENT
ROUTE
TO
FUNCTIONALIZED
ALLYLZIRCONOCENES
99
3.3.5.2
INSERTIONS
INTO
ZIRCONACYCLES
100
3.3.5.3
INSERTION
OF
BENZYL
CARBENOIDS
INTO
ZIRCONACYCLES
101
3.3.5.4
INSERTION
OF
HALO-SUBSTITUTED
CARBENOIDS
INTO
ZIRCONACYCLES
102
3.3.6
INSERTION
OF
METALATED
EPOXIDES
INTO
ORGANOZIRCONIUM
SPECIES
103
3.3.6.1
INSERTION
OF
1
-NITRILE-1-LITHIO
EPOXIDES
INTO
ACYCLIC
ORGANOZIRCONOCENE
CHLORIDES
103
3.3.6.2
INSERTION
OF
1-SILYL-,
1-NITRILE,
AND
1
-ARYL-1-LITHIO
EPOXIDES
INTO
ZIRCONACYCLES
104
3.3.7
REGIOCHEMISTRY
OF
CARBENOID
INSERTION
INTO
ZIRCONACYCLES
104
3.4
CONCLUSION
106
REFERENCES
AND
NOTES
108
4
HYDROZIRCONATION
AND
FURTHER
TRANSMETALATION
REACTIONS
110
BRUCE
H.
LIPSHUTZ,
STEVEN
S.
PFEIFFER,
KEVIN
NOSON,
AND
TAKASHI
TOMIOKA
4.1
INTRODUCTION
110
4.2
HYDROZIRCONATION/QUENCHING
112
4.3
HYDROZIRCONATION:
RING-FORMING
AND
RING-OPENING
REACTIONS
115
4.4
ACYL
ZIRCONOCENES
116
4.5
ALLYLIC
ZIRCONOCENES
119
XIV
I
CONTENTS
4.6
4.7
4.8
4.9
4.10
4.11
CROSS-COUPLING
REACTIONS
121
ZIRCONIUM
TO
COPPER
127
ZIRCONIUM
TO
ZINC
132
ZIRCONIUM
TO
BORON
137
ZIRCONIUM
TO
NICKEL
138
SUMMARY
AND
OUTLOOK
139
REFERENCES
146
5
ACYLZIRCONOCENES
IN
ORGANIC
SYNTHESIS
149
YUJI
HANZAWA
5.1
5.2
5.3
5.3.1
5.3.2
INTRODUCTION
149
SYNTHESIS
AND
STABILITY
OF
ACYLZIRCONOCENE
COMPLEXES
149
REACTIONS
OF
ACYLZIRCONOCENE
COMPLEXES
150
HISTORICAL
BACKGROUND
150
CONVERSION
TO
KETONE
-
AND
KETENE
-
ZIRCONOCENE
COMPLEXES
AND
REACTIONS
THEREOF
151
5.3.2.1
5.3.2.2
5.4
KETONE
-
ZIRCONOCENE
COMPLEXES
151
KETENE
-
ZIRCONOCENE
COMPLEXES
153
REACTIONS
OF
ACYLZIRCONOCENE
CHLORIDES
AS
"
UNMASKED
"
ACYL
GROUP
DONORS
154
5.4.1
5.4.2
5.4.3
5.4.3.1
5.4.3.2
5.4.4
5.4.4.1
5.4.4.2
5.4.4.3
5.4.4.4
5.4.4.5
5.4.4.6
5.4.5
5.5
INTRODUCTORY
REMARKS
154
REACTION
WITH
ALDEHYDES
155
REACTIONS
WITH
IMINES
157
YB(OTF)
3
/TMSOTF-CATALYZED
REACTIONS
157
BRONS
TED
ACID-CATALYZED
REACTIONS
WITH
IMINES
159
REACTIONS
WITH
A,
0
UNSATURATED
KETONES
161
1,2
AND
1,4-SELECTIVE
ADDITIONS
TO
A,0-ENONE
DERIVATIVES
161
ENANTIOSELECTIVE
1,2-SELECTIVE
ADDITION
TO
A,0-ENONE
DERIVATIVES
163
1,4-SELECTIVE
ADDITION
TO
A,0-YNONE
DERIVATIVES
165
PD-CATALYZED
COUPLING
REACTIONS
168
CU-CATALYZED
CROSS-COUPLING
REACTIONS
170
GENERATION
OF
SELENO
AND
TELLUROESTERS
173
CATIONIC
ACYLZIRCONOCENE
COMPLEXES
173
REACTIVITY
OF
A,0-UNSATURATED
ACYLZIRCONOCENE
CHLORIDES
TOWARD
NUCLEOPHILES
174
5.6
CONCLUSION
176
REFERENCES
AND
NOTES
178
6
CHIRAL
ZIRCONIUM
CATALYSTS
FOR
ENANTIOSELECTIVE
SYNTHESIS
180
AMIR
H.
HOVEY
DA
6.1
6.2
6.2.1
INTRODUCTION
180
ZR-CATALYZED
ENANTIOSELECTIVE
C
-
C
BOND-FORMING
REACTIONS
180
ZR-CATALYZED
ENANTIOSELECTIVE
ALKYLATION
OF
ALKENES
WITH
GRIGNARD
REAGENTS
181
6.2.1.1
INTERMOLECULAR
CATALYTIC
ASYMMETRIC
ALKYLATIONS
181
CONTENTS
IXV
6.2.1.2
6.2.2
6.2.3
6.2.4
INTRAMOLECULAR
CATALYTIC
ASYMMETRIC
ALKYLATIONS
186
ZR
-
CATALYZED
KINETIC
RESOLUTION
OF
UNSATURATED
HETEROCYCLES
188
ZR-CATALYZED
KINETIC
RESOLUTION
OF
EXOCYCLIC
ALLYLIC
ETHERS
191
ZR-CATALYZED
ENANTIOSELECTIVE
ALKYLATION
OF
ALKENES
WITH
ALKYLALUMINUM
REAGENTS
194
6.2.5
6.2.6
ZR-CATALYZED
ENANTIOSELECTIVE
ALLYLATION
OF
ALDEHYDES
197
ZR-CATALYZED
ENANTIOSELECTIVE
IMINE
ALKYLATIONS
WITH
ALKYLZINC
REAGENTS
199
6.2.7
6.2.8
ZR-CATALYZED
ENANTIOSELECTIVE
CYANIDE
ADDITION
TO
ALDEHYDES
202
ZR-CATALYZED
ENANTIOSELECTIVE
CYANIDE
ADDITIONS
TO
IMINES
(STRECKER
REACTIONS)
204
6.2.9
6.2.10
6.2.11
6.2.11.1
6.2.11.2
6.2.12
6.2.13
6.3
6.4
6.5
ZR-CATALYZED
ENANTIOSELECTIVE
ALDOL
ADDITIONS
207
ZR-CATALYZED
ENANTIOSELECTIVE
MANNICH
REACTIONS
209
ZR-CATALYZED
ENANTIOSELECTIVE
CYCLOADDITIONS
212
CYCLOADDITIONS
WITH
CARBONYL
DIENOPHILES
212
CYCLOADDITIONS
WITH
IMINE
DIENOPHILES
215
ZR-CATALYZED
ENANTIOSELECTIVE
ALKENE
INSERTIONS
217
ZR-CATALYZED
ENANTIOSELECTIVE
ADDITIONS
TO
MESO
EPOXIDES
217
ZR-CATALYZED
ENANTIOSELECTIVE
C
-
N
BOND-FORMING
REACTIONS
218
ZR-CATALYZED
ENANTIOSELECTIVE
C
-
H
BOND-FORMING
REACTIONS
219
SUMMARY
AND
OUTLOOK
223
REFERENCES
224
7
GEM-METALLOZIRCONOCENES
IN
ORGANIC
SYNTHESIS
230
VALERY
M.
DEMBITSKY
AND
MORRIS
SREBNIK
7.1
7.2
7.2.1
INTRODUCTION
230
1,1-ALUMINIOZIRCONOCENE
COMPLEXES
231
SYNTHESIS
OF
STABLE
PLANAR
TETRACOORDINATE
CARBON
ZR/AL
COMPOUNDS
233
7.3
7.3.1
7.3.2
7.3.3
7.3.4
7.3.5
1,1-BORIOZIRCONOCENE
COMPLEXES
237
GEM-1,
1-BORIOZIRCONOCENE
ALKANES
237
USE
OF
GEM-BORAZIRCONOCENE
ALKANES
IN
REGIOSELECTIVE
SYNTHESIS
239
HALOGENATION
OF
GEM-BORIOZIRCONOCENE
COMPLEXES
241
DIASTEREOSELECTIVE
HYDROZIRCONATION
244
PREPARATION
OF
DIBORABUTADIENES
BY
ZIRCONOCENE-MEDIATED
COUPLING
247
7.3.6
7.3.7
7.3.8
7.3.9
7.3.10
AMINATION
OF
BORIOZIRCONOCENE
COMPLEXES
247
(E)-L,L-BIMETALLIC
BORIOZIRCONOCENE
ALKENES
249
HYDROLYSIS
OF
(Z)-L-ALKENYLBORONATES
250
SYNTHESIS
OF
CYCLIC
BORIOZIRCONOCENES
252
BIMETALLIC
BORIOZIRCONOCENE
COMPLEXES
WITH
PLANAR
TETRACOORDINATE
CARBON
253
7.4
7.5
7.5.1
1,1-LITHIOZIRCONOCENE
REAGENTS
256
1,1-STANNIOZIRCONOCENE
REAGENTS
256
GEM-STANNIOZIRCONOCENE
ALKANES
256
XVI
I
CONTENTS
7.5.2
7.5.3
7.5.4
7.5.5
7.5.6
7.6
7.6.1
7.7
7.8
7.8.1
7.9
7.10
TRANSMETALATION
REACTIONS
257
PREPARATION
OF
HALOGENATED
ALKENES
259
BICYCLIZATION
OF
ENYNES
262
ZIRCONIUM-PROMOTED
BICYCLIZATION
OF
STANNYLENYNE
DERIVATIVES
263
BICYCLIZATION
OF
DIYNES
264
1,1-GALLIOZIRCONOCENE
COMPLEXES
265
EXCHANGE
REACTIONS
OF
GALLIOZIRCONOCENE
COMPLEXES
268
1,1-GERMANIOZIRCONOCENE
COMPLEXES
269
1,1-ZINCIOZIRCONOCENE
REAGENTS
269
PREPARATION
OF
POLYFUNCTIONALIZED
ALKENES
270
1,1-DIZIRCONOCENE
COMPLEXES
273
CONCLUSION
276
REFERENCES
277
8
CATIONIC
ZIRCONOCENE
SPECIES
IN
ORGANIC
SYNTHESIS
282
KEISUKE
SUZUKI,
LUKAS
HINTERMANN,
AND
SHIGEO
YAMANOI
8.1
8.1.1
8.1.2
8.1.3
8.1.4
8.1.5
8.2
8.2.1
8.2.2
8.2.2.1
8.2.2.2
GENERAL
INTRODUCTION
282
DEFINITION
OF
CATIONIC
ZIRCONOCENES
IN
THIS
REVIEW
282
CONDITIONS
FOR
THE
GENERATION
OF
CATIONIC
ZIRCONOCENE
283
STRUCTURE
AND
REACTIVITY
OF
CATIONIC
ZIRCONOCENES
283
AVAILABILITY
285
REACTIONS
INVOLVING
CATIONIC
ZIRCONOCENES
285
GLYCOSYLATIONS
WITH
CP
2
ZRCL
2
/SILVER
SALT
ACTIVATORS
286
CP
2
ZRCL
2
/SILVER
SALT
AS
A
NEW
ACTIVATOR
OF
GLYCOSYL
FLUORIDES
286
APPLICATIONS
IN
SYNTHESIS
287
APPLICATION
TO
GLYCOSIDE
AND
NUCLEOSIDE
SYNTHESIS
287
APPLICATION
TO
GLYCOSYLPHOSPHATIDYLINOSITOL
(GPI)
ANCHOR
AND
INOSITOL
PHOSPHOGLYCAN
(IPG)
SYNTHESIS
289
8.2.2.3
8.2.2.4
8.2.2.5
8.2.2.6
DIVERSE
OLIGOSACCHARIDE
SYNTHESES
292
CYCLOGLYCOSYLATION
294
GLYCOCONJUGATE
SYNTHESIS
295
CONCLUSIONS
ON
THE
USE
OF
THE
ZIRCONOCENE/SILVER
PERCHLORATE
ACTIVATOR:
MODIFICATION
AND
TUNING
OF
THE
REAGENT
296
8.2.3
8.3
8.3.1
ACTIVATION
OF
GLYCOSYL
SULFOXIDES
296
NUCLEOPHILIC
ADDITIONS
TO
ALDEHYDES
AND
EPOXIDES
297
SILVER-MEDIATED
1,2
-ADDITION
OF
ALK(EN)YLZIRCONOCENE
CHLORIDES
TO
ALDEHYDES
[48]
297
8.3.1.1
8.3.1.2
8.3.2
1,3-DIENE
SYNTHESIS
FROM
ALDEHYDES
299
HOMOLOGATION
OF
ALDEHYDES
300
NUCLEOPHILIC
RING-OPENING
OF
EPOXIDES
BY
ALKYLZIRCONOCENE
CHLORIDES
300
8.3.3
NUCLEOPHILIC
REACTIONS
OF
ORGANOZIRCONOCENE
CHLORIDES
WITH
EPOXIDES
300
CONTENTS
I
XVII
8.4
8.4.1
8.4.1.1
8.4.1.2
8.4.1.3
8.4.1.4
8.4.2
8.5
8.5.1
8.5.2
8.5.3
8.5.4
8.5.5
8.5.6
8.6
8.7
CARBOMETALATION
OF
ALKYNES
AND
ALKENES
302
CARBOMETALATION
OF
ALKYNES
303
METHYLALUMINATION
303
OTHER
ALKYLALUMINATIONS
303
ALLYLZIRCONATION
304
ALKYLZIRCONATION
305
CARBOMETALATION
OF
ALKENES
306
CATIONIC
ZIRCONOCENE
COMPLEXES
AS
LEWIS
ACID
CATALYSTS
308
EPOXY
ESTER
TO
ORTHOESTER
REARRANGEMENT
308
EPOXIDE
TO
ALDEHYDE
REARRANGEMENT
310
DIELS
-
ALDER
REACTION
310
CATIONIC
DIELS
-
ALDER
REACTION
312
CATALYTIC
MUKAIYAMA
ALDOL
REACTION
313
SILYL
KETENE
ACETAL
TO
A-SILYL
ESTER
ISOMERIZATION
314
MISCELLANEOUS
REACTIONS
314
CONCLUSION
315
REFERENCES
317
9
TITANIUM(LL)
ALKOXIDES
IN
ORGANIC
SYNTHESIS
319
FUMIE
SATO
AND
HIROKAZU
URABE
9.1
9.2
INTRODUCTION
319
GENERATION
OF
(R|
2
-ALKYNE)TI(OIPR)
2
AND
ITS
UTILIZATION
IN
ORGANIC
SYNTHESIS
320
9.3
PREPARATION
OF
ALLYL
AND
ALLENYLTITANIUM
REAGENTS
AND
THEIR
SYNTHETIC
UTILITY
331
9.4
INTRAMOLECULAR
NUCLEOPHILIC
ACYL
SUBSTITUTION
(INAS)
MEDIATED
BY
1
337
9.5
9.6
INTRAMOLECULAR
COUPLING
OF
ALKENES
AND
ACETYLENES
342
CONCLUDING
REMARKS
350
REFERENCES
351
10
ORGANOMETALLIC
CHEMISTRY
OFTITANOCENE
AND
ZIRCONOCENE
COMPLEXES
WITH
BIS(TRIMETHYLSILYL)ACETYLENE
AS
THE
BASIS
FOR
APPLICATIONS
IN
ORGANIC
SYNTHESIS
355
UWE
ROSENTHAL
AND
VLADIMIR
V.
BURLAKOV
10.1
10.1.1
10.1.2
INTRODUCTION
355
ESTABLISHED
TITANOCENE
AND
ZIRCONOCENE
SOURCES
355
NOVEL
TITANOCENE
AND
ZIRCONOCENE
REAGENTS
WITH
BIS(TRIMETHYLSILYL)ACETYLENE
356
10.1.3
10.2
10.2.1
10.3
MECHANISTIC
CONSIDERATIONS
358
REACTIONS
OFTITANOCENE
AND
ZIRCONOCENE
SOURCES
358
ACETYLENES
-C=C
-
359
ALKENES
C=C
361
XVIIII
CONTENTS
10.4
10.4.1
10.4.2
10.5
10.5.1
10.5.2
10.6
10.6.1
10.6.2
10.7
10.7.1
10.7.2
10.7.3
10.7.4
10.7.5
10.7.6
10.7.7
10.8
10.9
DIACETYLENES
363
NON-CONJUGATED
OC
-
X
-
C=C
363
CONJUGATED
C=C
-
C=C
364
DIALKENES
371
NON-CONJUGATED
C=C
-
X
-
C=C
371
CONJUGATED
C=C
-
C=C
371
DOUBLE
BONDS
TO
HETEROATOMS
C=X(
-
)
371
CARBONYL
COMPOUNDS
C=O
371
IMINES
C=N
372
SELECTED
COMBINATIONS
OF
FUNCTIONAL
GROUPS
372
C=C-C=C
373
C=C-C=O
373
C=C-C=N
373
C=C-C=O
374
C=C-C=N
375
N=C-C=N
376
C=N-N=C
376
MISCELLANEOUS
377
SUMMARY
AND
OUTLOOK
383
REFERENCES
387
11
TITANIUM-MEDIATED
SYNTHESES
OF
CYCLOPROPANOLS
AND
CYCLOPROPYLAMINES
390
ARMIN
DE
MEIJERE,
SERGEI
I.
KOZHUSHKOV,
AND
ANDREI
I.
SAVCHENKO
11.1
11.2
INTRODUCTION
390
REACTION
MODES
OF
TITANIUM
ALKYL
DERIVATIVES
POSSESSING
0-HYDROGEN
ATOMS
391
11.3
11.3.1
11.3.2
11.4
11.4.1
11.4.2
11.4.3
11.5
PREPARATION
OF
CYCLOPROPANOLS
392
FROM
ORGANOMAGNESIUM
PRECURSORS
392
VIA
LIGAND-EXCHANGED
TITANIUM-ALKENE
COMPLEXES
398
PREPARATION
OF
CYCLOPROPYLAMINES
405
FROM
ORGANOMAGNESIUM
PRECURSORS
405
VIA
LIGAND-EXCHANGED
TITANIUM-ALKENE
COMPLEXES
410
FROM
ORGANOZINC
PRECURSORS
415
APPLICATIONS
IN
NATURAL
PRODUCT
SYNTHESES
AND
SYNTHESES
OF
COMPOUNDS
WITH
POTENTIALLY
USEFUL
PROPERTIES
417
11.5.1
TRANSFORMATIONS
OF
CYCLOPROPANOLS
WITH
RETENTION
OF
THE
CYCLOPROPANE
RING
418
11.5.2
TRANSFORMATIONS
OF
CYCLOPROPANOLS
WITH
CLEAVAGE
OF
THE
CYCLOPROPANE
RING
419
11.5.3
11.6
TRANSFORMATIONS
OF
CYCLOPROPYLAMINES
422
CONCLUSION
425
REFERENCES
430
CONTENTS
I
XIX
12
TITANOCENE-CATALYZED
EPOXIDE
OPENING
435
ANDREAS
GANSAUER
AND
BJORN
RINKER
12.1
12.2
12.3
12.3.1
INTRODUCTION
435
STOICHIOMETRIC
OPENING
OF
EPOXIDES
BY
ELECTRON
TRANSFER
435
TITANOCENE-CATALYZED
EPOXIDE
OPENING
439
TITANOCENE-CATALYZED
REDUCTIVE
EPOXIDE
OPENING
TO
ALCOHOLS
439
12.3.2
TITANOCENE-CATALYZED
ADDITIONS
TO
A,0-UNSATURATED
CARBONYL
COMPOUNDS
442
12.3.3
12.3.4
12.3.5
12.4
TITANOCENE-CATALYZED
5
-EXO
CYCLIZATIONS
443
TITANOCENE-CATALYZED
RADICAL
TANDEM
REACTIONS
444
CATALYTIC
ENANTIOSELECTIVE
EPOXIDE
OPENING
445
CONCLUSION
448
REFERENCES
449
13
SYNTHESIS
AND
REACTIVITY
OF
ALLYLTITANIUM
DERIVATIVES
451
JAN
SZYMONIAK
AND
CLAUDE
MOISE
13.1
13.2
13.2.1
13.2.1.1
13.2.1.2
13.2.1.3
13.2.2
13.3
13.4
13.4.1
13.4.2
INTRODUCTION
451
ALLYL
BIS(CYCLOPENTADIENYL)TITANIUM
REAGENTS
452
PREPARATION
AND
PROPERTIES
OF
T]
3
-ALLYLTITANOCENES
452
REACTIONS
WITH
ALDEHYDES
AND
KETONES
453
OTHER
ELECTROPHILES
AND
DIENE
PRECURSORS
454
ASYMMETRIC
REACTIONS
WITH
R]
3
-ALLYLTITANOCENES
458
PREPARATION
AND
REACTIONS
OF
R]
1
-
ALLYL
TITANOCENES
459
ALLYL
MONO(CYCLOPENTADIENYL)TITANIUM
REAGENTS
460
ALLYLTITANIUM
REAGENTS
WITHOUT
CYCLOPENTADIENYL
GROUPS
464
SYNTHESIS
BY
TRANSMETALLATION
AND
SELECTIVE
ALLYLATION
REACTIONS
464
ALLYLTITANIUMS
FROM
ALLYL
HALIDES
OR
ALLYL
ALCOHOL
DERIVATIVES
AND
TI(II)
AND
THEIR
SYNTHETIC
UTILITY
467
13.5
CONCLUSION
469
REFERENCES
473
14
TITANIUM-BASED
OLEFIN
METATHESIS
AND
RELATED
REACTIONS
475
TAKESHI
TAKEDA
14.1
14.2
INTRODUCTION
475
REACTIONS
OF
TITANIUM
CARBENE
COMPLEXES
WITH
CARBON
-
CARBON
DOUBLE
BONDS
475
14.2.1
14.2.2
14.2.3
OLEFIN
METATHESIS
475
FORMATION
OF
TITANOCENE-METHYLIDENE
AND
ITS
REACTION
WITH
OLEFINS
476
FORMATION
OF
TITANOCENE-ALKYLIDENES
AND
THEIR
APPLICATION
TO
OLEFIN
METATHESIS
479
14.2.4
PREPARATION
OF
TITANOCENE-ALKYLIDENES
FROM
THIOACETALS
AND
THEIR
APPLICATION
TO
OLEFIN
METATHESIS
480
14.2.5
OTHER
TRANSFORMATIONS
OF
TITANACYCLOBUTANES
485
XX
I
CONTENTS
14.3
REACTIONS
OF
TITANIUM
CARBENE
COMPLEXES
WITH
CARBON
-
OXYGEN
DOUBLE
BONDS
487
14.3.1
14.3.2
14.4
14.4.1
14.4.2
14.5
METHYLENATION
OF
CARBONYL
COMPOUNDS
487
ALKYLIDENATION
OF
CARBONYL
COMPOUNDS
488
REACTIONS
OF
TITANIUM
CARBENE
COMPLEXES
WITH
TRIPLE
BONDS
493
REACTION
OF
TITANIUM
CARBENE
COMPLEXES
WITH
ALKYNES
493
THE
REACTION
OF
TITANIUM
CARBENE
COMPLEXES
WITH
NITRILES
495
CONCLUSION
497
REFERENCES
498
INDEX
501 |
| any_adam_object | 1 |
| building | Verbundindex |
| bvnumber | BV014279931 |
| callnumber-first | Q - Science |
| callnumber-label | QD262 |
| callnumber-raw | QD262 |
| callnumber-search | QD262 |
| callnumber-sort | QD 3262 |
| callnumber-subject | QD - Chemistry |
| classification_rvk | VH 9700 VK 5500 |
| classification_tum | CHE 630f CHE 622f CHE 330f |
| ctrlnum | (OCoLC)248888444 (DE-599)BVBBV014279931 |
| dewey-full | 547.0551 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.0551 |
| dewey-search | 547.0551 |
| dewey-sort | 3547.0551 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Chemie |
| format | Book |
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| id | DE-604.BV014279931 |
| illustrated | Illustrated |
| indexdate | 2024-08-22T00:31:32Z |
| institution | BVB |
| isbn | 3527304282 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-009793068 |
| oclc_num | 248888444 |
| open_access_boolean | |
| owner | DE-703 DE-29T DE-355 DE-BY-UBR DE-19 DE-BY-UBM DE-91G DE-BY-TUM DE-11 |
| owner_facet | DE-703 DE-29T DE-355 DE-BY-UBR DE-19 DE-BY-UBM DE-91G DE-BY-TUM DE-11 |
| physical | XXV, 512 S. Ill. : 24 cm |
| publishDate | 2002 |
| publishDateSearch | 2002 |
| publishDateSort | 2002 |
| publisher | WILEY-VCH |
| record_format | marc |
| spelling | Titanium and zirconium in organic synthesis ed. by Ilan Marek Weinheim WILEY-VCH 2002 XXV, 512 S. Ill. : 24 cm txt rdacontent n rdamedia nc rdacarrier Composés organiques - Synthèse Composés organiques titanés Composés organiques zirconiés Organic compounds Synthesis Organotitanium compounds Organozirconium compounds Organische Synthese (DE-588)4075695-6 gnd rswk-swf Zirkoniumverbindungen (DE-588)4190957-4 gnd rswk-swf Titanorganische Verbindungen (DE-588)4043813-2 gnd rswk-swf Titanverbindungen (DE-588)4185575-9 gnd rswk-swf Zirkoniumorganische Verbindungen (DE-588)4190954-9 gnd rswk-swf Organische Synthese (DE-588)4075695-6 s Zirkoniumorganische Verbindungen (DE-588)4190954-9 s DE-604 Titanorganische Verbindungen (DE-588)4043813-2 s Titanverbindungen (DE-588)4185575-9 s Zirkoniumverbindungen (DE-588)4190957-4 s Marek, Ilan Sonstige oth DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009793068&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Titanium and zirconium in organic synthesis Composés organiques - Synthèse Composés organiques titanés Composés organiques zirconiés Organic compounds Synthesis Organotitanium compounds Organozirconium compounds Organische Synthese (DE-588)4075695-6 gnd Zirkoniumverbindungen (DE-588)4190957-4 gnd Titanorganische Verbindungen (DE-588)4043813-2 gnd Titanverbindungen (DE-588)4185575-9 gnd Zirkoniumorganische Verbindungen (DE-588)4190954-9 gnd |
| subject_GND | (DE-588)4075695-6 (DE-588)4190957-4 (DE-588)4043813-2 (DE-588)4185575-9 (DE-588)4190954-9 |
| title | Titanium and zirconium in organic synthesis |
| title_auth | Titanium and zirconium in organic synthesis |
| title_exact_search | Titanium and zirconium in organic synthesis |
| title_full | Titanium and zirconium in organic synthesis ed. by Ilan Marek |
| title_fullStr | Titanium and zirconium in organic synthesis ed. by Ilan Marek |
| title_full_unstemmed | Titanium and zirconium in organic synthesis ed. by Ilan Marek |
| title_short | Titanium and zirconium in organic synthesis |
| title_sort | titanium and zirconium in organic synthesis |
| topic | Composés organiques - Synthèse Composés organiques titanés Composés organiques zirconiés Organic compounds Synthesis Organotitanium compounds Organozirconium compounds Organische Synthese (DE-588)4075695-6 gnd Zirkoniumverbindungen (DE-588)4190957-4 gnd Titanorganische Verbindungen (DE-588)4043813-2 gnd Titanverbindungen (DE-588)4185575-9 gnd Zirkoniumorganische Verbindungen (DE-588)4190954-9 gnd |
| topic_facet | Composés organiques - Synthèse Composés organiques titanés Composés organiques zirconiés Organic compounds Synthesis Organotitanium compounds Organozirconium compounds Organische Synthese Zirkoniumverbindungen Titanorganische Verbindungen Titanverbindungen Zirkoniumorganische Verbindungen |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009793068&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT marekilan titaniumandzirconiuminorganicsynthesis |