Page 1328 - Advanced Organic Chemistry Part B - Reactions & Synthesis

cuprates, 676 aldol reactions, 69, 73, 76–77 1305
alkenyl, 679 alkylation, 25–26
cyano, 677, 679–680 reduction, 407–409 Index
mixed, 677–680 Cyclopropanes
stannyl, addition to alkynes, 834 enantioslective synthesis by cyclopropanation,
magnesium, mixed organometallic reagents, 931–934
695–697 catalysts for, 931, 933
mechanisms examples, 935
computational interpretation of, 697–702 Simmons-Smith reagent for, 916–917, 919–923
preparation of, 675–680 computational model of, 922–923
reactions with enantioselective, 920
allylic acetates, 682–683 examples, 916–917
epoxides, 685–686 hydroxyl group directing effect in, 921–922
halides and sulfonates, 680–685 Lewis acid catalysis of, 917
unsaturated ketones and esters, 686–694 synthesis using sulfur ylides, 177
reactivity, summary, 705–706 synthesis by carbene addition reactions, 916–934
structure of, 675–677 examples, 931–932
zinc, mixed organometallic reagent, 694–695 synthesis by metallocarbenes, 921–927
conjugate addition of, 694–696 copper catalysts for, 924–925
Copper bis-oxazolines examples, 931–932
as chiral catalysts for rhodium catalysts for, 931–932
aldol reaction, 128 Cyclopropanones, as intermediates in Favorskii
conjugate addition, 195–196 reaction, 893–895
Diels-Alder reactions, 507 Cyclopropenes
Mannich reactions, 143 from alkenyl carbenes, 941
Crabtree catalyst Cyclopropylidene, ring-opening to allenes, 941
homogenous hydrogenation, 375–376
Crown ethers
catalysis of nucleophilic substitution by, 224–225 Danishefsky diene, see 1,3-butadiene,
enolate reactivity, effect on, 20 1-methoxy-3-trimethylsiloxy-
Cuprates, see Copper, organo- compounds Darzens reaction, 182
Curtius rearrangement, 947–950 Decalones, alkylation 26–27
isocyanates from, 947–949 Decarbonylation
diphenylphosphoryl azide as reagent, 948 acyl halides, 760–761
macrolactonization by, 948 aldehydes, 760
Cyanide ion bicycle[2.2.1]heptadien-7-ones, 593
conjugate addition by, 198–199 Decarboxylation
Cyanoethyl as protecting group, 1251 in acylation of malonate enolates, 152
Cyclization in amine-catalyzed condesnsation reactions,
electrophilic of alkenes, 310–328 147–148
radical, 967–973 of -keto acids, 23–24
in reductive by SMI 2 , 448–449 of malonic acids, 23–24
Cycloaddition reactions oxidative by
1,3-dipolar, 526–538 bromine/iodosobenzene diacetate, 1147
examples, 535 bromine/mercuric oxide, 1147
ylides gernerated from carbenes, 938, 940 lead tetraacetate, 1145–1147
[2+2], 538–543 via radical intermediates, 957, 986
alkenes and carbonyl compounds, 548–551 Dess-Martin reagent, 1072–1073
alkenes and enones, 545–548 Dianions
alkenes and ketenes, 539–541, 543 of dicarbonyl compounds
photocycloadditions of enones, 545–548, 1092 alkylation, 36–37
zwitterionic intermediates in, 542 generation, 36
Cyclobutadiene DCCI, see Dicyclohexylcarbodiimide
iron tricarbonyl complex, 768 Diazaborolidines
Cyclobutanes boron enolates from, 118–119
syntesis by [2+2] cycloaddition, 538–543 Diaziridines
Cyclobutanones carbenes from, 913
by ketene cycloadditions, 539–543 Diazo compounds
Cyclohexanones acyl, 910–911