Page 1324 - Advanced Organic Chemistry Part B - Reactions & Synthesis

Hofmann rearrangement, 949 Aziridines 1301
hydroboration-amination, 346, 351 azomethine ylides from, 531
organocerium addition to hydrazones, 666 from alkenes, 947 Index
reduction of amides, 398, 400, 404–405 Azo compounds
reductive amination, 403–404 thermal elimination reactions, 593–596
Amino acids
synthesis by
Baccatin III, multistep synthesis, 1210–1220
amidocarbonylation of aldehydes, 754
acyclic precursors for, 1216
enantioselective hydrogenation, 380, 384
fragmentation reaction in, 1210, 1215
(R -N-amino2-methoxymethylpyrrolidine
(RAMP), 53 Mukaiyama reaction in, 1218
(S -N-amino2-methoxymethylpyrrolidine Pyrone diels-alder reaction in, 1212
(SAMP), 53 Baeyer-Villiger oxidation, 1134–1138
Ammonium ylides Baldwin’s rules, 310–311
N-allyl, [2,3]-sigmatropic rearrangement of, Barbier reaction, 644
584–585 Barton deoxygenation, 460–461, 961
examples, 586 9-BBN, see 9-borabicyclo[3.3.1]nonane
formation using diazo compounds, 584–585 Benzothiazoles
Antisynthetic transforms, 1164 sulfones of in Julia reaction, 175
Aromatic compounds Benzoxazolium salts
biaryls, synthesis of 2-choloro in conversion of alcohols
copper-catalyzed, 703–705 to chlorides, 221
nickel-catalyzed, 755–756, 758–759 Benzyloxycarbonyl
chromium tricarbonyl complexes, 769–770 amine protective group 268
Aromatic substitution, see also halogenation, Benzyne
Nitration aromatic as intermediate in nucleophilic aromatic
Birch reduction, 436–438 substitution, 1039–1042
chloromethylation, 1023 cycloaddition reactions of, 1041–1042
diazonium ion intermediates for, 1003, ene reaction of, 1041
1027–1035 generation, 1039–1040
electrophilic, 1003, 1004–1027 BINAP, see Bis-(2,2’-diphenylphosphinyl)-1,
formylation, 1024 1’-binaphthyl 1,1’-binaphthalene-2,2’-diol,
Friedel-Crafts acylation, 1017–1023 complexes as enantioselective catalysts for
Friedel-Crafts alkylation, 1014–1017 Diels-Alder reaction, 510–512
halogenation, 1008–1014 BINOL, see 1,1’-binaphthalene-2,2’-diol,
mercuration, 1026 complexes as enantioselective catalysts for
metal-catalyzed, 1004, 1042–1052 Biomimetic synthesis, 142
nitration, 1004–1008 Bis-(4-bromo-2,6-di-t-butylphenoxy)
nucleophilic, 1004, 1027 methylaluminum (MABR)
addition-elimination mechanism, catalyst for Mukaiyama aldol reaction, 84
1035–1037 catalyst for Diels-Alder reaction, 500
elimination-addition mechanism, Birch reduction, 436–439
1039–1042 examples, 438
metal-catalyzed, 1042–1052 9-borabicyclo[3.3.1]nonane, 338–339
radical, 1052–1053 Borane, derivatives
side-chain oxidation, 1148–1149 alkenyl
S RN 1 mechanism for, 1053–1055 in alkene synthesis, 797–798
thallation, 1026 palladium-catalyzed coupling, 740–741
Vilsmeier-Haack reaction, 1024 alkynyl, addition to aldehydes, 805
Azetidinones allylic, 784
reduction of, 405 addition reactions with aldehydes, 797–809
Azides t-butyl (isopinocampheyl) chloro
acyl, isocyanates from, 947–948 as reducing agent, 415–416
alkyl, by nucleophilic substitution, 231–232 bis-(1,2-dimethylpropyl), 338
aryl, from aryl diazonium ions, 1032 bis-(iso-2-ethylapopinocampheyl) chloro
nitrenes from, 944, 946 as reducing agent, 416
reactions with bis-(isopinocampheyl)
boranes, amines from, 344 addition reaction of b-allyl, 799
ketones, lactams from, 953 hydroboration by, 349–350