Page 1332 - Advanced Organic Chemistry Part B - Reactions & Synthesis

silyl, rearrangement, 1114 aromatic 1309
synthesis, see also Epoxidation dissolving metal reduction, 436
by Darzens reaction, 182 aryl vinyl Index
from ketones and sulfur ylides, 177–179 Claisen rearrangement of, 564
2-trimethylsilyl, synthesis, 182 benzyl
Eschenmoser’s salt, 140 hydrogenolysis, 394, 396
Esters cleavage of, 239–240
allylic cyclic
copper-catalyzed coupling formation by oxymercuration, 325–326
palladium catalyzed carbonylation, 751 halo, by halocyclization, 311, 317–318
reaction with carbocations, 863 oxidation
allyloxycarbonyl, as protective groups for by ruthenium tetroxide, 1069
alcohols, 266 protective groups for alcohols
benzoate allyl, 264
by oxidation of ethers, 1069 benzyl, 262–263
boron enolates of, 80–81 t-butyl, 262
condensation reactions of, 149–150 dimethoxybenzyl, 263
dealkylation by trimethylsilyl iodide, 240 2,4-dimethoxytriphenylmethyl, 262
-diazo synthesis from
synthesis, 912 alcohols, 227
enolates of, 79, 568 alkenes by addition of alcohols, 294
chelation effects in, 571–572 ketones and silyl ethers, 427–428
conjugate addition reactions, 186–188, 190 1-ethoxyethyl
intramolecular alkylation, 36 as hydroxy protective group, 260
zinc, 657–659
as hydroxy protective groups
allyloxycarbonyl, 266 Favorskii rearrangement, 892–895
trichloroethoxycarbonyl, 265 mechanism, 894–895
lithium enolates of Felkin model
aldol reactions of, 78–81 aldol reaction, 90–91
alkylation, 31–33 ketone reduction, 410–411
formation of, 78–81 Ferrocene, 768
chelation in, 32–33, 80 Fischer esterification, 252
silyl ketene acetals from, 79 Fischer-Tropsch process, 760
partial reduction of, 401–403 Fluoride ion
-sulfonyl as base in conjugate addition, 184
palladium-catalyzed allylation of, 714 in allyl silane additions, 826, 832–833
synthesis from Fluorination
aldehydes, 1131 alkenes, 303–304
boranes by halo enolate homologation, ketones, 331
792–793 Formamidines
carboxylic acids, 227–228, 252 lithiation of, 630
-diazo ketones, by Wolff rearrangement, Formylation
941–946 aromatic, 1024
ketones by Baeyer-Villiger oxidation, Fragmentation reactions
1134–1139 carbocations, 897–900
thermal elimination reactions of, 601–603 in Baccatin III synthesis, 1211–1219
, -unsaturated in longifolene synthesis, 1191
conjugate addition by organocopper radicals, 984–985
compounds, 686–695 reductive, 461
synthesis by Wadsworth-Emmons reaction, Free radicals, see Radicals
164–166 Friedel-Crafts acylation, 1017–1023
Ethers catalyst for, 1017
allyl examples, 1022–1023
[2,3]-sigmatropic rearrangement of anions, intramolecular, 1016–1020
587–588 mechanism, 1019
allyl vinyl Friedel-Crafts alkylation reaction, 1014–1017
Claisen rearrangement, 561–564 by benzyl cations, 425
formation, 561–562 examples, 1017