Page 1320 - Advanced Organic Chemistry Part B - Reactions & Synthesis

Index

Acetals as alkenes, 881–883
electrophiles in intramolecular, 882–883
allyl silane addition, 820–821 amines, 252–257
Mukaiyama aldol reaction, 85–86 carbon nucleophiles, 148–149
protective groups for enolates, 150–157
alcohols, 258–262 ester condensation, 149–157
carbonyl compounds, 272–275 malonate magnesium salts, 152
diols, 266–267 silanes, ketones from, 828–829
Acrylic acid derivatives Acylium ions
-amido, hydrogenation of in Friedel-Crafts reaction, 1019
computational model for, 380–382 reaction with alkenes, 881–883
enantioselective, 380, 384 Acyloin condensation, 450
enantioselective hydrogenation, 380 mechanism, 450
examples, 385–386 Alcohols
Acyl anion equivalents, 1167–1169 acylation of, 243–252
Acyl chlorides by acyl halides, 246
-halogenation, 331 by acyl imidazolides, 246–247
reaction with by Fischer esterification, 252
organocadmium compounds, 661–662 by pyridine-2-thiol estes, 248
organomagnesium compounds, 637–638 catalysis by DMAP, 244
organozinc compounds, 661 Lewis acid catalysts for, 242
silanes, 828–829 using 3-chloroisoxazolium salts, 247
synthesis using using 2-chloropyridinium salts, 247
oxalyl chloride, 243 using DCCI, 247
triphenylphosphine, carbon tetrachloride, 244 allylic
Acyl iminium ions, 145–146, 199, 828–829 epoxidation of, 1082–1088
Acylation of synthesis
alcohols, 243–252 from aldehydes and allylic boron
by acyl halides, 244 compounds, 797–809
by acyl imidazolides, 246–247 from aldehydes and allylic silanes, 815–830
by pyridine-2-thiol esters, 248 from alkenes and selenium dioixide,
catalysis by DMAP, 244 1124–1126
Lewis acid catalysts for, 245–246 from alkenes and singlet oxygen,
using 3-chloroisoxazolium salts, 247 1117–1124
using 2-chloropyridinium salts, 247 from epoxides by base-catalyzed ring
using DCCI, 247 opening, 1114–1116
1297