Page 1339 - Advanced Organic Chemistry Part B - Reactions & Synthesis

1316 Oxidation of (Cont.) organometallic reagents, 723–728
ketones, 1131–1143 organotin reagents, 731–738
Index Baeyer-Villiger, 1134–1139 Heck reaction, 715–723
Oxime ethers, in radical cyclizations, 973, 974, hydrocarbonylation, 749–750
979–981 oxidative cyclization, 711–712
Oximes solvocarbonylation, 749–750
amides from, by Beckmann rearrangement, Pantolactone as chiral auxiliaries for
951–955 Diels-Alder reaction, 599–504
fragmentation of, 952 Paterno-buchi reaction, 548–552
Bis-(2-oxo-3-oxazoldinyl) phosphinic chloride PCC, see chromium oxidants
Amide synthesis by, 253 PDC, see chromium oxidants
Oxy-cope rearrangement, 553, 556–559 Peroxycarboxylic acids
anionic, 556–559 alkene epoxidation, 1091–1096
in synthesis of juvabione, 1183 Baeyer-Villiger reaction, 1136–1138
examples, 557–559 Peterson reaction, 171–174
examples, 173–174
Oxygen, singlet
Phase transfer catalysis
alkene oxidation by, 1117–1126
in nucleophilic substitution, 224–226
examples, 1121
Phosphate esters
in zeolite, 1120, 1121
allylic
mechanism, 1119, 1121
palladium-catalyzed carbonylation, 753
regioselectivity, 1126
reductive cleavage, 439–440
generation, 1118
Phosphines
reaction with
as ligands in
enaminoketones, 1124
enantioselective hydrogenation, 376–384
enol ethers, 1122
enolate arylation, 728–730
Oxymercuration, 293–298
Heck reaction, 715
alcohols from, 295–298
palladium-catalyzed aromatic substitution,
computation model of, 297–298
1045–1046, 1048–1049
cyclization by, 324–327
palladium-catalyzed cross-coupling, 739, 783
ethers from, 297–298
Phosphite esters
examples, 298
synthesis by Mitsunobu reaction, 228
stereochemistry of, 295–297
Phosphonate esters
Ozonolysis
in wadsworth-emmons reaction, 164–170
alkenes, 1129–1131
Phosphonium ions
examples, 1131
alkoxy, as intermediates in nucleophilic
substitution, 219–221
vinyl, as dienophiles in Diels-Alder reaction, 494
Palladacycle
Phosphonium ylides
as catalyst in Heck reaction, 715–723
in wittig reaction, 157–164
Palladium, organo-, intermediates,
stabilized, 159
706–754
Phosphorus tribromide
acylation of
reaction with alcohols, 218–221
organotin compounds, 833, 839
Photochemical cycloaddition reactions, 544–551
-allyl, 369, 707, 712, 713, 751, 754
alkene photodimerization, 544–545
nucleophilic substitution of, 712–715 copper triflate catalysis of, 544–545
alkene oxidation, 709–712 enones, 545–549
mechanism, 709 in synthesis of longifolene, 1086
alkene arylation, 715–719 Phthalimides
mechanism, 716–717 as amine protective group, 269
-elimination reactions of, 707, 709, 712, 716, in Gabriel amine synthesis, 229–230
717, 723 Pinacol borane, see borane, pinacol
carbonylation reactions of, 708, 748–752 Pinacol rearrangement, 883–889
catalysis of aromatic substitution, 1042–1052 examples, 888
mechanism, 1046–1047 of epoxides, 886
cross-coupling reactions of, 708, 723–739 stereochemistry of, 884–886
enol sulfonate esters, 730 sulfonate esters in, 884–886
boron compounds, 739–746 tandem with carbonyl-ene reaction, 886–887