Page 1334 - Advanced Organic Chemistry Part B - Reactions & Synthesis

Hydrogen halides (Ipc) 2 BCl, see Borane, bis-(isopinocampheyl) 1311
addition to alkenes, 290–293 chloro
addition to alkynes, 333–337 IpcBH 2 , see Borane, isopinocampheyl Index
Hydrogenolysis (Ipc) 2 BH, see Borane, bis-(isopinocampheyl)
benzyl ethers, 394, 396 Ireland-Claisen rearrangement, 567–576
N-hydroxysuccinimide in amide synthesis, boat versus chair transition structure, 569–570
253–254, 1248 chelation effects in, 571–572
Hydrozirconation, 356–358 enantioselective catalysts for, 572–573
Hypophosphorous acid examples, 574–575
as hydrogen atom donor in reduction, 432, 460 Lewis acid catalysis, 572
in reductive dediazonization, 1029 stereochemistry of, 567–571
Iron, organo- compounds
cyclobutadiene tricarbonyl complex, 769
Imidazole ferrocene, 768
N-acyl Isocyanates, synthesis from
acylation of alcohols by, 246–247, 265 acyl azides, 947–948
enolate acylation, 154 N-bromo amides, 949
Imidazolidines
catalysts for
Jones reagent, 1065
enolate arylation, 730
Julia olefination reaction, 174–176
olefin metathesis, 761
examples, 176
Imidazolyl disulfide
Julia-Kocienski reaction, 174
macrolactonization by, 249
Julia-Lythgoe reaction, 174
Imides
Juvabione, multistep syntheses of, 1174–1186
N-acyliminium ions from, 145
Imine anions, 48–52 diastereoselective from cyclohexenone,
1179–1180
alkylation of, 50–52
enantioselective, 1182–1185
enantioselective, 51–52
from aromatic starting materials, 1175–1176
as nucleophiles, 1
from terpene starting materials, 1176–1181
Imines, reactions with
[2,3]-sigmatropic rearrangement in, 1183
silyl enol ethers, 142–143
stereocontrolled, 1180–1181
silyl ketene acetals, 145
zincate reagents, 659
Iminium ions Ketenes
n-acyl [2+2]cycloaddition reactions with alkenes,
addition reactions of, 195–196, 828 539–541
formation of, 195–196 examples, 543
intermediates in intramolecular, 540–541
Mannich reactions, 140–143 intermediates in Wolff rearrangement, 941–943
Knoevenagel reactions, 147–148 B-ketoesters
reactions with alkylation of, 22–24
allylic silanes, 828–829 Ketones
organozinc compounds, 652 -acetoxy
Indium, organo- compounds from acetoxy epoxides, 1112–1113
from allylic halides, 663–664 from enol ethers, 1133
Indium trichloride from silyl enol ethers, 1133–1134
catalyst for Mukaiyama aldol reaction, 84 reduction of, 441–442
Indole aldol reactions of, 65–78
palladium-catalyzed arylation, 1045 -alkoxy
Iodination, aromatic, 1013 aldol reactions of, 92, 109
Iodine azide, 305 reactions with organometallic compounds, 650
Iodine atom transfer, 970, 972 reduction by hydride donors, 411, 413
Iodine isocyanate, 305 -alkoxy from Mukaiyama reactions, 86–87
Iodine nitrate, 305 examples, 88
Iodine thiocyanate, 305 alkylation of, 24–31
Iodobenzene diacetate, oxidation of amides, 950 examples, 29–30
Iodolactonization, 312–316 -amino
examples, 315–316 preparation by Mannich reaction, 140–141