Page 1344 - Advanced Organic Chemistry Part B - Reactions & Synthesis

as co-reagent in conversion of alcohols to ethylmagnesium bromide dimeric di-iso-propyl 1321
halides, 217–222 ether complex, 621, 623, 624
Triphenylsilyl bis-iodomethylzinc complex with exo, Index
as hydroxyl protective group, 265, 266 exo-dimethoxybornane, 919
Tris-(trimethylsilyl) silane, as hydrogen atom lanthanum (R R -phenylpy BOX
donor, 431–433, 963 trifluoromethanes sulfonate
Tropinone, synthesis of, 142 tetrahydrate, 510
lithium enolate of methyl t-butyl ketone, 11, 19
lithium salt of methyl t-butyl ketone
Ugi reaction, 1256
N-phenylimine anion, 49
Ullman coupling reaction, 703
lithium salt of SAMP hydrazone of
2-acetylnaphthalene, 53, 55
Vanadium monomeric and dimeric copper-carbene
catalysis of epoxidation, 1081, 1082 complexes with diimine ligand, 921, 922
reductive coupling by, 450 tetrakis-P,P,P’P’-(4-methylphenyl)-1,1’-
Vicarious nucleophilic aromatic substitution, 1037 binaphthyldiphosphine-1,2-diphenyl-1,2-
Vilsmeier-Haack reaction, 1024 ethaneamine ruthenium borohydride
Vinyl ethers, see enol ethers
catalyst, 393
phenyllithium tetrameric diethyl ether
Wacker oxidation, 710–711 complex, 626
Wadsworth-Emmons reaction, 164–170 scandium (S S phenylpyBOX
computational modeling of, 166–170 trifluoromethanesulfonate hydrate, 510
examples, 167–168 tin tetrachloride complex of
intramolecular, 166 2-benzyloxy-3-pentanone, 93
macrocyclization by, 166 titanium tetrachloride complex of O-acryloyl
stereoselectivity of, 165–166 ethyl lactate, 482
Weinreb amides, see amides, n-methoxy-n-methyl zinc enolate from t-butyl bromoacetate, 658
Wieland-Miescher ketone, 138
starting material for longifolene synthesis, 1188,
Yamaguchi method for macrolactonization, 249
1189–1195
Ylides
Wilkinson’s catalyst
ammonium, [2,3]-sigmatropic rearrangement of,
homogeneous hydrogenation, 374
583–585
hydroboration, 341
carbonyl
hydrosilation, 809, 810
from carbenes, 936–941
Wittig reaction, 157–164
phosphonium in wittig reaction, 157–164
application in synthesis, 163–164
-oxido in wittig reactions, 162
as example of generalized aldol reaction, 65, 150
sulfur
examples, 159
reactions with carbonyl compounds, 177–180
Schlosser modification, 162 [2,3]-sigmatropic rearrangement of, 581–598
stereoselectivity, 159
Wittig rearrangement, 587–589 Zinc, organo- reagents, 650–661
examples, 590 conjugate addition of, 198
stereochemistry, 587–588
Wolff-Kishner reduction, 453–454 cross-coupling
cobalt-catalyzed, 761
Wolff rearrangement, 941, 943, 944, 945 palladium-catalyzed, 723–729
mechanism, 941
zinc-catalyzed, 756–758
halomethyl, as carbene precursors, 916
Xanthates preparation of, 650–652
in radical deoxygenation, 433 from boranes, 652
thermal elimination reactions of, 601–602 reactions with, 651–655
X-ray structure of aldehydes, 653–656
(BINOLate) Ti 2 (O-i-Pr) 6 , 129 zincate reagents, 659–660
(BINOLate) Ti 3 (O-i-Pr) 10 , 129 Zinc borohydride
boron trifluoride complex of as reducing agent, 399
2-methylpropenal, 482 in reductive amination, 403, 404
, -diphenylprolinol oxazaborolidine catalyst, in reduction of -hydroxyketones, 412
418–420 Zirconium
ethylmagnesium bromide bis-diethyl ether enolates in aldol reactions, 76–78
complex, 621, 623 hydrozirconation, 355–357