Page 1342 - Advanced Organic Chemistry Part B - Reactions & Synthesis

conjugate addition reactions, 188, 189, Stille reaction, 731 1319
190–192, 193 Stryrene derivatives
[2+2]-cycloaddition reactions of, 542 enantioselective hydrogenation, 384–387 Index
as enolate equivalents, 82–86, 125–132, 139 Sulfate esters
enolates from, 11–16, 73 of vic-diols, reductive elimination, 452
epoxides of, 1107, 1111–1114 Sulfenylation
halogenation, 328–331 alkenes, 307–309
Mannich reactions of, 140, 142, 143 reagents for, 307, 308
Mukaiyama aldol reactions of, 82–87 carbonyl compounds, 331–332
[2+2]-photocycloaddition with carbonyl Sulfenylcyclization, 320–324
compounds, 551 examples, 322–323
oxidation, 1133–1134 Sulfides, organolithium compounds from, 625, 636
photochemical cycloaddition, 544–545 Sulfonamides
preparation protective groups for amines, 269
from carbonyl compounds, 12–15 radical reaction of, 989–891
by conjugate reduction of enones, 16–18 synthesis by Mitsunobu reaction, 228, 232
using lombardo’s reagent, 661 Sulfonate esters
reaction with diol
acyl iminum ions, 145, 146 pinacol rearrangement, 883–886
carbocation, 862, 863, 864 enol
imines, 142–145 palladium-catalyzed cross-coupling, 728–729
Silyl ketene acetals, 78, 79 reactions with
alkylation, 863, 864 organocopper compounds, 675, 680
formation from esters, 79, 567–569 reduction, 422–423
Ireland-Claisen rearrangement of, 567–576 synthesis
Mukaiyama aldol reactions of, 96 by Mitsunobu reaction, 228, 232
reaction with from alcohols, 216
carbocations, 861–863, 864 Sulfolene dioxide
Silyl thioketene acetals cheletropic elimination of, 591–592
aldol reactions, 82 Sulfones
conjugate addition reactions, 191–192, 193 cyclohexyl 2-naphthyl as chiral auxiliary, 42–43
Mukaiyama reactions, 131, 133 -halo
Simmons-Smith reaction, 916, 917, 919 Ramberg-Backlund reaction of, 895–897
computational model of, 922, 925 -hydroxy
examples, 930–933 reductive elimination in Julia reaction,
hydroxy group directing effect in, 919, 920 174–176, 460
Lewis acid catalysis of, 917 Julia olefination reactions of, 174–176
Sodium bis-(2-methoxyethoxy) aluminum hydride vinyl, as dienophiles in Diels-Alder reaction,
partial reduction of esters by, 401 492–494
Sodium borohydride Sulfonium ylides, 177–179
as reducing agent, 396–399, 409, 411 allylic, [2,3]-sigmatropic rearrangement of, 581,
Sodium hexamethyldisilazide 583–587
base for enolate formation, 5 examples, 586
Sodium triacetoxyborohydride formation using diazo compounds, 583–584
as reducing agent, 405, 406, 407, 411–413 Sulfoxides
Sodium tris-(1-methylpropyl) borohydride, as acylation of, 155
reducing agent, 399–400 allylic, [2,3]-sigmatropic rearrangement of,
Solid phase synthesis, 1245–1252 581–583
oligonucleotides, 1250–1252 -keto, 154–156
polypeptides, 1245–1250 Sulfoximines
Sonogashira reaction, 726 as alkylidene transfer reagents, 270
Squalene Sulfur ylides
polyene cyclization in steroid biosynthesis, reactions with carbonyl compounds, 177–179
867–868 [2,3]-sigmatropic rearrangement, 583–585
S RN 1 substitution, 1053–1055 Suzuki reaction, 739
mechanism, 1054 Swern oxidation, 1070
Stannanes, see tin, organo- compounds Synthetic equivalents, 1166–1171
Stannyl enol ethers cyanide as nucleophilic carboxy equivalent, 1170
conjugate addition reactions, 193 in Diels-Alder reaction, 491–493