Page 1323 - Advanced Organic Chemistry Part B - Reactions & Synthesis

1300 Alkylation (Contd.) N-methoxy-n-methyl
tandem with conjugate addition, 189–190 acylation of enolates by, 154
Index torsional effect in, 27–28 ketones from, 645
Friedel-Crafts, 1014–1016 reduction of, 401
Alkoxyphosphonium ions primary, from nitriles, 256
as intermediates in nucleophilic substitution, partial reduction by DiBAlH, 264
219–221 protective groups for
Alkynes dimethoxyphenyl, 271
alkenyl 4-methoxyphenyl, 271
synthesis by cross-coupling, 734–735 oxidative rearrangement of, 949, 952
chlorination, 335–336 reactions with
hydroalumination, 357 organocerium compounds, 666
hydroboration, 352 reduction by
hydrogen halide addition, 334–335 alane, 405
hydrogenation, partial, 387 borane, 400, 404–405
hydrozirconation, 356–357 lithium aluminum hydride, 398
mercury-catalyzed hydration, 335–336 synthesis of, 252–257
metathesis reaction with alkenes, coupling reagents for, 253–254, 1248–1249
764–765 from ketones by schmidt reaction, 950–951
in epothilone a synthesis, 1225 oximes by Beckmann rearrangement, 951
oxidation Schotten-Bauman conditions for, 252
potassium permanganate, 1074 thiono
ruthenium dioxide, 1075 reduction of, 405
palladium-catalyzed coupling, 726–728 [3,3]-sigmatropic rearrangement of, 579
reactions with , -unsaturated
organocopper-magnesium organometallic conjugate addition reactions of, 197
reagents, 695–697 , -unsaturated from O-allyl ketene aminals,
organotin hydrides, 833–834 576–577
reduction by unsaturated
dissolving metals, 439 halocyclization of, 320
LiALH 4 , 423–425 mercurocyclization, 326
synthesis from Amine oxides
boranes by homologation, 796–797 N-allyl, [3,3]-sigmatropic rearrangement of, 582
Allene thermal elimination reactions of, 597–598, 602
addition reactions, 333–334 Amines
protonation, 333–334 acylation of, 252–258, 1248–1249
synthesis arylation
from cyclopropylidenes, 941 copper-catalyzed, 1043–1044
Allylboration, 799–809; see also Aldehydes, palladium-catalyzed, 1047
reaction with, allylic boranes catalysts for Knoevenagel reactions, 147–148
computational model for, 801–802 N-chloro, radical reaction of, 990
enantioselective, 799, 804–805 enantioselective synthesis
examples, 806–807 by hydroboration-amination, 351
Lewis acid catalysis of, 802 protective groups for, 267–272
stereoselectivity, 798–799, 805 allyloxycarbonyl, 268–269
Allyloxycarbonyl benzyl, 269
amine protecting group, 268–269 benzyloxycarbonyl, 268, 396
Alpine-Hydride®, see lithium fluorenylmethoxycarbonyl 1247
B-isopinocampheyl-9- 2-nitrobenzyl, 269
borabicyclo[3.3.1]nonane hydride 4-pentenoyl, 271
Amides phthalimides, 270
N-alkylation of, 230 t-butoxycarbonyl, 268, 1246
N-allyl enolates sulfonamides, 271
[3,3]-sigmatropic rearrangement of, 578 trichloroethoxycarbonyl, 268
O-alkylation of, 230 trifluoroacetyl, 270
N-bromo, rearrangement of, table of, 272
949–950 synthesis by
N-iodo, radical reaction of, 990 Curtius rearrangement, 947–948
lithiation of, 631 Gabriel method, 229–230