Page 1326 - Advanced Organic Chemistry Part B - Reactions & Synthesis

singlet, 903, 906, 916 Fischer-Tropsch process, 760 1303
substituent effects on, 904, 909 palladium-catalyzed, 748–754
triplet, 903, 906, 916 Carbonyl-ene reaction, 869–881 Index
ylides, generation by, 938, 940 computational model for, 872–873
Carboalumination enantioselective catalysts for, 874–875
alkenes, 354–355 examples, 878–879
alkynes, 356–357 intramolecular, 875–877
examples, 357 Lewis acid catalysts for, 870, 874
Carbocations mechanism, 870–871
alkylation by, 862–863 stereoselectivity of, 871, 873
Friedel-Crafts reaction, 1014–1017 tandem with
as intermediates, 862–892 Mukaiyama reaction, 876
fragmentation reactions of, 897–900 pinacol rearrangement, 886–888
polyene cyclization, 864–869 Sakurai reaction, 877
rearrangement of, 883–892 Carboxylic acid derivatives
pinacol, 883–889 acyl chlorides, synthesis of, 243–244
reduction by silanes, 425–428 partial reduction of, 401–403
Carbocation rearrangements substitution reactions of, 242–256
during alkene chlorination, 301 Carboxylic acids
during reaction of alkenes with hydrogen aromatic
halides, 291 dissolving metal reduction, 439
Carbometallation reactions by synthesis by oxidation, 1148–1149
alkylaluminum compounds, 353–357 conversion to esters
copper-magnesium reagents, 695–697 using cesium salts, 227–228
zirconium compounds, 356–357 dianions
Carbonate esters alkylation of, 33–34
iodocyclization, 314, 317 esterification of
protecting group for diols, 267 by nucleophilic substitution, 227–228
Carbonyl compounds, see also Aldehydes; Esters; diazo compounds, 227
Ketones fischer, 252
-halogenation, 328–331 -keto, decarboxylation of, 23–24
[2+2]-photocycloaddition with alkenes, oxidative decarboxylation, 1145–1148
548–551 protective groups for
reaction with orthoesters, 275–276
allylic silanes, 815–827 oxazolines, 275
allylic tin compounds, 836–850 reactions with
organomagnesium compounds, 637–644 diazomethane, 227
phosphonium ylides, 157–164 trimethysilyldiazomethane, 227
phosphonate anions, 164–170 reduction by
-silyl carbanions, 171–174 diborane, 400
sulfones anions, 174–176 synthesis from
reductive coupling of 444–452 alkenes by hydrocarbonylation, 749–750
examples, 451 boronic acids, 345
mechanism, 447–448 malonate esters by alkylation, 22–23
reductive deoxygenation, 452–457 methyl ketones by oxidation by
Clemmensen reduction, 452–453 hypochlorite, 329
via dithiolanes, 453–454 organomagnesium compounds by
via N-sulfonyl hydrazones, 453 carbonation, 638
Wolff-Kishner reduction, 453 unsaturated
-selenylation, 331–333 enantioselective hydrogenation of, 378–379
-sulfenylation, 331–333 iodolactonization of, 312–316
synthesis from , -unsaturated
alkenes by hydroboration-oxidation, 345 from amine-catalyzed condensation reactions,
, -unsaturated 147–148
from Claisen rearrangement, 561–564 , -unsaturated
from Ireland-Claisen rearrangement, 567–576 synthesis by orthoester Claisen rearrangement,
Carbonylation reactions 564–567
boranes, 786–787 Catechol borane, see Borane, derivatives, catechol
hydroformylation, 759–760 Cbz, see benzyloxycarbonyl