Cumulative Subject Index | Organic Reactions

Chapter and Topic Index, Volumes 1–118

Many chapters contain brief discussions of reactions and comparisons of alternative synthetic methods related to the reaction that is the subject of the chapter. These related reactions and alternative methods are not usually listed in this index. In this index, the volume number is in boldface, the chapter number is in ordinary type.

Click any reference below to go directly to that chapter. Also available as the original PDF .

A B C D E G H I K L M N O P R S T U V W X Y Z

A

Acetoacetic ester condensation, 1.9

Acetylenes

cotrimerizations of, 68.1
oxidations by dioxirane, 69.1
reactions with Fischer carbene complexes, phenol and quinone formation, 70.2
synthesis of, 5.1; 23.3; 32.2

Achmatowicz reaction, 87.1

Acid halides

reactions with esters, 1.9
reactions with organometallic compounds, 8.2

α-Acylamino acid mixed anhydrides, 12.4

α-Acylamino acids, azlactonization of, 3.5

Acylation

enantioselective, 104.1
intramolecular, to form cyclic ketones, 2.4; 23.2
of esters with acid chlorides, 1.9
of ketones to form diketones, 8.3

Acyl fluorides, synthesis of, 21.1; 34.2; 35.3

Acyl hypohalites, reactions of, 9.5

Acyloins, 4.4; 15.1; 23.2

1,4-Additions, 118.1

Alcohols

conversion to fluorides, 21.1; 21.2; 34.2; 35.3
conversion to olefins, 12.2
deoxygenation of, 77.2
oxidation of, 6.5; 39.3; 53.1; 74.2
replacement of hydroxyl group by nucleophiles, 29.1; 42.2
resolution of, 2.9

Alcohols, synthesis

by allylstannane addition to aldehydes, 64.1
by aminooxygenation of alkenes, 108.2
by base-promoted isomerization of epoxides, 29.3
by hydroboration, 13.1
by hydroxylation of ethylenic compounds, 7.7
by organochromium reagents to carbonyl compounds, 64.3
by reduction, 6.10; 8.1; 71.1
from organoboranes, 33.1; 73.1
of propargylic alcohols, 100.4

Aldehydes, additions of allyl, allenyl propargyl stannanes, 64.1

addition of allylic boron compounds, 73.1
addition of perfluoroalkyl reagents, 91.1

Aldehydes, catalyzed addition to double bonds, 40.4

Aldehydes, dimerization by alkoxides, 86.2

Aldehydes, synthesis of, 4.7; 5.10; 8.4; 8.5; 9.2; 33.1; 107.1

Aldimines, 99.1

Aldol condensation, 16.1; 67.1

catalytic, enantioselective, 67.1
directed, 28.3
with boron enolates, 51.1

Aldol reactions, 98.2

Aldol-Tishchenko reaction, 86.2

Aliphatic fluorides, 2.2; 21.1; 21.2; 34.2; 35.3

Alkaloids as catalysts for enantioselective Michael reactions, 90.1

Alkanes: by reduction of alkyl halides with organochromium reagents, 64.3

of carbonyl groups with organosilanes, 71.1
oxidation of, 69.1
via alcohol deoxygenation, 77.2

Alkenes

aminooxygenation of, 108.2
arylation, 11.3; 24.3; 27.2
asymmetric dihydroxylation of, 66.2
carbozincation of, 87.3
copper-boryl additions, 100.15
cross-metathesis of, 106.1
cyclopropanes from, 20.1
cyclization in intramolecular Heck reactions, 60.2
from carbonyl compounds with organochromium reagents, 64.3
dioxirane epoxidation of, 61.2
epoxidation and hydroxylation of, 7.7
epoxidation of electron-deficient, 74.3
free-radical additions to, 13.3; 13.4
halofunctionalization of, 105.1
hydroamination of
hydroboration of, 13.1
hydrocyanation of, 75.1
hydrogenation with homogeneous catalysts, 24.1
oxidation with palladium catalyst, 84.2
perfluoroalkylation of, 91.1
reactions with diazoacetic esters, 18.3
reactions with nitrones, 36.1
reduction by alkoxyaluminum hydrides diimides organosilanes perfluoroalkylation of, 34.1; 40.2; 71.1; 91.1

Alkenes, synthesis

by addition of sulfones to carbonyl compounds by Bamford-Stevens reaction by Claisen and Cope rearrangements by dehydrocyanation of nitriles by deoxygenation of vicinal diols by deoxygenative coupling of carbonyl compounds by Julia-Kocienski olefination by palladium-catalyzed vinylation by pyrolysis of xanthates by McMurray reaction by Wittig reaction from amines from aryl and vinyl halides from α-halosulfones from phosphoryl-stabilized anions from silicon-stabilized anions from tosylhydrazones from twofold extrusion reactions, 95.1; 23.3; 22.1; 30.2; 82.1; 95.1; 27.2; 12.2; 82.1; 14.3; 11.5; 27.2; 25.1; 62.2; 25.2; 38.1; 23.3; 39.1; 78.3
Alkenyl- and alkynylaluminum reagents, 32.2
Alkenyl-electrophiles lithium reagents, formation of silanes trifluoroborates, 83.1; 39.1; 75.3; 79.1
Alkoxyaluminum hydride reductions, 34.1; 36.3
Alkoxyphosphonium cations, nucleophilic displacements on, 29.1
Alkoxysilanes, 75.3
Alkylation of allyl alcohol esters of allylic and benzylic carbanions with amines and ammonium salts of aromatic compounds of esters and nitriles γ-, of dianions of β-dicarbonyl compounds iridium-catalyzed allylic of metallic acetylides of nitrile-stabilized carbanions with organopalladium complexes, 84.1; 27.1; 7.3; 3.1; 9.4; 17.2; 99.2; 5.1; 31.1; 27.2
Alkyl azides, use in Schmidt Reaction, 78.1
Alkylidenation by titanium-based reagents, 43.1
Alkylidenesuccinic acids, synthesis and reactions of, 6.1
Alkylidene triphenylphosphoranes synthesis and reactions of, 14.3

Alkylidyne, 102.2

Alkynes

alkyne-metal complexes, 103.3
cross coupling, 116.1
cycloisomerizations with alkenes and arenes, 92.1
hydroamination of, 88.1
hydroarylation of, 103.1
hydrocyanation of, 75.1
hydrozincation of, 87.3
hydrozirconation of, 113.2
metathesis, 102.2
perfluoroalkylation of, 91.1

Alkynyl

silanes, 75.3
trifluoroborates, 79.1

Allenes, hydroamination of, 88.1

Allenyl esters, azide additions, 92.2

Allenylsilanes, electrophilic substitution reactions of, 37.2

Allylboration of carbonyl compounds, 73.1

Allylic alcohols, synthesis

from epoxides, 29.3
by Wittig rearrangement, 46.2

Allylic amines, 83.2

Allylic and benzylic carbanions heteroatom-substituted, 27.1

Allylic cations, 115.1

Allylic hydroperoxides, in photooxygenations, 20.2

Allylic rearrangements, transformation of glycols into 2,3-unsaturated glycosyl derivatives, 62.4

Allylic rearrangements, trihaloacetimidate, 66.1

π-Allylnickel complexes, 19.2

Allylphenols, synthesis by Claisen rearrangement, 2.1; 22.1

Allylsilanes, 75.3

Allylsilanes, electrophilic substitution reactions of, 37.2

Allylstannanes, 110.1

Allyl transfer reactions, 73.1

Aluminum alkoxides

in Meerwein-Ponndorf-Verley reduction, 2.5
in Oppenauer oxidation, 6.5

Amides

arylation of, 85.1
cyclopropanation of, 77.1
formation by oxime rearrangement, 35.1
from ketones, 78.1
in hydroamination of alkenes, 88.1
synthesis, 97.2

α-Amidoalkylations at carbon, 14.2

Amination

electrophilic, of carbanions and enolates, 72.1
of alkenes, 88.1
of aryl halides, 100.14
of heterocyclic bases by alkali amides, 1.4
of hydroxy compounds by Bucherer reaction, 1.5

Amine oxides

Polonovski reaction of, 39.2
pyrolysis of, 11.5

Amines

β-phenethylamines, 114.1
N-arylation of, 85.1
coupling with alcohols, 118.2
from allylstannane addition to imines, 64.1
from carbocations, 78.1
from carboxylic acids, 3.9; 78.1
from chiral N-sulfinyl imines, 99.1
oxidation of, 69.1
perfluoroalkylation of, 91.1
synthesis from organoboranes, 33.1
synthesis by hydroamination of alkenes, 88.1
synthesis by reductive alkylation, 4.3; 5.7
synthesis by Zinin reaction, 20.4
reactions with cyanogen bromide, 7.4

α-Amino acid derivatives

from borono-Mannich reactions, 83.2

α-Amino acid synthesis

by olefin ring-closing metathesis, 89.1
by the Strecker reaction, 70.1

α-Aminoalkylation of activated olefins, 51.2

α-Amino ketones

from borono-Mannich reactions, 83.2
from oxime derivatives, 78.2

Aminooxygenation of alkenes, 108.2

Aminophenols from anilines, 35.2

Anhydrides of aliphatic dibasic acids Friedel-Crafts reaction with, 5.5

Anion-assisted sigmatropic rearrangements, 43.2

Annulation reactions, 107.2

Anthracene homologs, synthesis of, 1.6

Anti-Markownikoff hydration of alkenes, 13.1

Arene synthesis, 109.1

π-Arenechromium tricarbonyls, reaction with nitrile-stabilized carbanions, 31.1

η -(Arene)chromium complexes, 67.2

Arndt-Eistert reaction, 1.2

Aromatic aldehydes, synthesis of, 5.6; 28.1

Aromatic compounds chloromethylation of polycyclic, 1.3; 107.2

Aromatic fluorides, synthesis of, 5.4

Aromatic hydrocarbons, synthesis of, 1.6; 30.1

Aromatic substitution by the S 1 reaction RN, 54.1

Arsinic acids, 2.10

Arsonic acids, 2.10

Arylacetic acids, synthesis of, 1.2; 22.4

β-Arylacrylic acids, synthesis of, 1.8

Aryl amines, reactions of, 1.5; 85.1

Arylation by aryl halides by copper catalysis by diazonium salts γ-, of dianions of β-dicarbonyl compounds of alkenes of enolates of ketones of nitrile-stabilized carbanions, 27.2; 85.1; 11.3; 24.3; 17.2; 11.3; 24.3; 27.2; 93.1; 76.2; 76.2; 31.1

Aryl diazoacetates, 75.2

Arylglyoxals, condensation with aromatic hydrocarbons, 4.5

Aryl halides amination of cross-coupling homocoupling of in hydroarylation of alkynes, 100.14; 83.1; 63.3; 103.1

Arylsilanes, 75.3

Arylsulfonic acids, synthesis of, 3.4

Aryl thiocyanates, 3.6

Aryltrifluoroborates, 79.1

Asymmetric aldol reactions using boron enolates, 51.1

Asymmetric catalysis, 100.6

Asymmetric coupling, 113.1

Asymmetric cyclopropanation, 57.1
Asymmetric deprotonation with chiral lithium amides, 79.2
Asymmetric dihydroxylation, 66.2
Asymmetric enyne cycloisomerizations, 92.1
Asymmetric epoxidation, 48.1; 61.2; 74.3
Asymmetric functionalization, 105.1
Asymmetric hydroamination of alkenes, 88.1
Asymmetric hydrocyanation, 75.1
Asymmetric hydrogenation of C=N, 74.1
Asymmetric induction, 105.2
Asymmetric Michael reactions, 90.1
Asymmetric reduction, 71.1
Asymmetric rhodium-catalyzed 1,4 additions of organoboranes to electron-deficient alkenes, 93.1
Asymmetric Strecker reaction, 70.1
Asymmetric synthesis, 110.2
Atom transfer formation of radicals, 48.2
Atropisomers, 117.2
Axial chirality, 117.2
Aza-Achmatowicz reaction, 87.1
Aza-Cope/Mannich reaction, 75.4
Aza-Payne rearrangements, 60.1
Azaphenanthrenes, synthesis by photocyclization, 30.1
Azides, synthesis and rearrangement of, 3.9; 92.2
2H-Azirines, from Neber rearrangement of oxime derivatives intermediates in vinyl azide cyclizations, 78.2; 92.2
Azlactones, 3.5
Azomethine imines, 103.2
Baeyer-Villiger reaction, 9.3; 43.3
Bamford-Stevens reaction, 23.3
Barbier Reaction, 58.2
Bart reaction, 2.10
Barton fragmentation reaction, 48.2
Barton-McCombie reaction, 77.2
Béchamp reaction, 2.10
Beckmann rearrangement, 11.1; 35.1
Benzils, reduction of, 4.5
Benzoin condensation, 4.5
Benzoquinones acetoxylation of, 19.3
in Nenitzescu reaction, 20.3
synthesis of, 4.6

B

Benzylic carbanions, 27.1; 67.2

Benzylic deprotonations, 79.2

Benzyl

silanes, 75.3
trifluoroborates, 79.1

Biaryls, synthesis of, 2.6; 63.3; 79.1

Bicyclobutanes, from cyclopropenes, 18.3

Biginelli dihydropyrimidine synthesis, 63.1

Birch reaction, 23.1; 42.1

Bischler-Napieralski reaction, 6.2

Bis(chloromethyl) ether, 1.3

Borane reagents, for allylic transfer, 73.1

rhodium-catalyzed 1,4-additions to electron-deficient alkenes, 93.1

Borohydride reduction, chiral, 52.2

in reductive amination, 59.1

Boron-boron bonds

activation of, 105.2

Boron enolates, 51.1

Boron-containing heterocycles synthesis

by olefin ring-closing metathesis, 89.1

Boronic acid Mannich reaction, 83.2

1,4-additions to electron-deficient alkenes, 93.1

Boronic ester, 105.3

Boyland-Sims oxidation, 35.2

Breslow intermediates, 106.2

Brook Rearrangement, 102.1

Bucherer reaction, 1.5; 85.1

Butenolides from furan oxidation, 87.1

C

Cadogan-Sundberg reaction, 111.2

Cannizzaro reaction, 2.3

Carbanion, electrophilic amination, 72.1

Carbazole synthesis

by aryl azide cyclization, 92.2
by reductive cyclization, 111.2

Carbenes, 13.2; 26.2; 28.1

Carbene complexes in phenol and quinone synthesis, 70.2

Carbenoids

in cyclopropanation −, 57.1; 58.1; 77.1
intermolecular C H insertions of, 75.2

Carbocycles, synthesis by ring-closing metathesis, 89.1

Carbohydrates, deoxy, synthesis of, 30.2

Carbometallocupration, 41.2

Carbon-carbon bond formation

by acetoacetic ester condensation, 1.9
by acyloin condensation, 23.2
by aldol condensation, 16.1; 28.3; 46.1; 67.1
by alkylation of allyl alcohol esters, 84.1
by alkylation with amines and ammonium salts, 7.3
by γ-alkylation and arylation, 17.2
by allylic and benzylic carbanions, 27.1
by amidoalkylation, 14.2
by asymmetric catalytic construction, 117.2
by Cannizzaro reaction −, 2.3
by C H activation reactions −, 100.11
by C H insertion reaction, 80.1
by Claisen rearrangement, 2.1; 22.1
by Cope rearrangement, 22.1
by cross-coupling with organotrifluoroborate salts transition-metal catalysts, 79.1; 113.1
by cyclopropanation reaction, 13.2; 20.1
by Darzens condensation, 5.10
by diazonium salt coupling, 10.1; 11.3; 24.3
by Dieckmann condensation, 15.1
by Diels-Alder reaction, 4.1; 4.2; 5.3; 32.1
by free-radical additions to alkenes, 13.3
by Friedel-Crafts reaction, 3.1; 5.5
by Knoevenagel condensation, 15.2
by Mannich reaction, 1.10; 7.3
by metallaphotoredox catalysis, 100.8
by Michael addition, 10.3; 90.1
by nitrile-stabilized carbanions, 31.1
by nitrone [3 + 2] cycloadditions with alkenes, 94.1
by organoboranes and organoborates, 33.1; 100.9
by organocopper reagents, 19.1; 38.2; 41.2
by organopalladium complexes, 27.2; 100.9
by organozinc reagents, 20.1; 100.1
by rearrangement of α-halo sulfones, 25.1; 62.2
by Reformatsky reaction, 1.1; 28.3
by rhodium-catalyzed 1,4-addition of organoboranes to electron-deficient alkenes, 93.1

Carbon-carbon bond formation: (Continued)

by trivalent manganese, 49.3
by Vilsmeier reaction, 49.1; 56.2
by vinylcyclopropane-cyclopentene rearrangement, 33.2

Carbon-fluorine bond formation, 21.1; 34.2; 35.3; 69.2; 100.12; 104.3

Carbon-halogen bond formation

by replacement of hydroxyl groups, 29.1

Carbon-heteroatom bond formation

by free-radical chain additions to carbon-carbon multiple bonds, 13.4
by organoboranes and organoborates, 33.1

Carbon-nitrogen bond formation

by copper-catalyzed arylation and vinylation, 85.1
by hydroamination of alkenes, 88.1
by reductive amination, 59.1
through hydrogen borrowing, 118.2

Carbon-phosphorus bond formation, 36.2

Carbonyl compounds, addition of organochromium reagents, 64.3

Carbonyl compounds, α,β-unsaturated

formation by Meyer–Schuster rearrangement, 115.2
formation by Saegusa reaction, 98.1
formation by selenoxide elimination, 44.1
vicinal difunctionalization of, 38.2

Carbonyl compounds, from nitro compounds, 38.3

in the Passerini Reaction, 65.1
oxidation with hypervalent iodine reagents, 54.2
reactions with allylic boron compounds, 73.1
reductive amination of, 59.1

Carbonyl ylides from diazo carbonyl compounds, 80.2

Carbonylation as part of intramolecular Heck reaction, 60.2

Carboxylic acids

synthesis from furan oxidation, 87.1
synthesis from organoboranes, 33.1
reaction with organolithium reagents, 18.1

Carboxylic acid derivatives

conversion to fluorides, 21.1; 21.2; 34.2; 35.3
cyclopropanation of, 77.1
Carbozincation, 87.3
Cascade reactions, 104.2
Catalysis asymmetric by gold, platinum, palladium by manganese, iron, cobalt cooperative, 117.2; 115.1; 100.7; 117.1
Catalytic asymmetric allylic alkylation, 84.1
Catalytic asymmetric hydrogenation of C=N functions, 74.1
Catalytic enantioselective aldol addition, 67.1
Catalytic enantioselective ketene cycloadditions, 82.2
Catalytic enantioselective Michael reaction, 90.1
Catalytic transfer hydrogenation, 100.6
Catellani reaction −, 117.1
C H functionalization −, 75.2; 80.1; 100.10; 100.11; 117.1
C H insertions intramolecular with carbenoids intermolecular with carbenoids, 80.1; 75.2
Chapman rearrangement, 14.1; 18.2
Chelation assistance, 100.10
Chemical protein synthesis, 97.2
Chemoselective ligation, 97.2
Chiral lithium amides, 79.2
Chiral ligands catalytic enantioselective Michael Reactions enantioselective hydroformylation of alkenes, 90.1; 93.1; 107.1
Chloromethylation of aromatic compounds, 2.3
Cholanthrenes, synthesis of, 1.6
Chromium reagents, 64.3; 67.2
Chugaev reaction, 12.2; 77.2
Claisen condensation, 1.8
Claisen rearrangement, 2.1; 22.1
Cleavage of benzyl-oxygen, benzyl-nitrogen, and benzyl-sulfur bonds of carbon-carbon bonds by periodic acid of esters via S 2-type dealkylation N of non-enolizable ketones with sodium amide in sensitized photooxidation, 7.5; 2.8; 24.2; 9.1; 20.2
Clemmensen reduction, 1.7; 22.3

Cloke–Wilson Rearrangement, 114.1

Collins reagent, 53.1

Combinatorial chemistry

Condensation

acetoacetic ester, 1.9
acyloin, 4.4; 23.2
aldol, 16.1
benzoin, 4.5
Biginelli, 63.1
Claisen, 1.8
Darzens, 5.10
Dieckmann, 1.9; 6.9; 15.1
directed aldol, 28.3
Knoevenagel, 1.8; 15.2
Stobbe, 6.1
Thorpe-Ziegler, 15.1

Conjugate additions

of hydrogen cyanide, 25.3; 75.1
of organocopper reagents, 19.1; 41.2; 118.1
of organoboranes to electron-deficient alkenes by rhodium catalysis, 93.1

Conjugated systems, 116.1

Conrotation, 117.3

Cope rearrangement, 22.1; 41.1; 43.2

Copper acetylide, 114.2

Copper-catalyzed additions, 118.1

Copper-catalyzed arylation

of active methylenes, 76.2
of nitrogen nucleophiles, 85.1

Copper-catalyzed preparation of indoles by cyclization, 76.3

Copper-Grignard complexes, conjugate additions of, 19.1; 41.2

Corey-Winter reaction, 30.2

Coumarins, synthesis of, 7.1; 20.3

Cross-coupling reactions with

alkenylzirconocene, 113.2
copper catalysis, 85.1
iron catalysts, 83.1
metallaphotoredox catalysis, 100.8
organosilicon compounds, 75.3
organostannanes, 50.1
organotrifluoroborate salts, 79.1
organozinc reagents, 100.1
Suzuki-Miyaura reaction, 100.9
terminal alkynes, 116.1
transition-metal catalysts, 113.1; 117.2

Cross-metathesis reactions

alkenes, 106.1

Cuprate reagents, 19.1; 38.2; 41.2

Curtius rearrangement, 3.7; 3.9

Cyanation, of N-heteroaromatic compounds, 70.1

perfluoroalkyl carbanions, 91.1

Cyanoborohydride, in reductive aminations, 59.1

Cyanoethylation, 5.2

Cyanogen bromide, reactions with tertiary amines, 7.4

Cyclic amino acids and peptidomimetics synthesis by olefin ring-closing metathesis, 89.1

Cyclic ketones, formation by intramolecular acylation, 2.4; 23.2

Cyclic nitrones, [3 + 2]cycloadditions with alkenes, 94.1

Cyclization

of alkyl dihalides, 19.2
of aryl-substituted aliphatic acids, acid chlorides, and anhydrides, 2.4; 23.2
of α-carbonyl carbenes and carbenoids, 26.2
cycloheptenones from α-bromo ketones, 29.2
of diesters and dinitriles, 15.1
Fischer indole, 10.2
intramolecular by acylation, 2.4
intramolecular by acyloin condensation, 4.4
intramolecular by Diels-Alder reaction, 32.1
intramolecular by Heck reaction, 60.2
intramolecular by Michael reaction, 47.2
Nazarov, 45.1; 117.3
of nitrogen-centered radicals, 108.1
by radical reactions, 48.2; 108.1
reductive, 111.2
of stilbenes, 30.1
tandem cyclization by Heck reaction, 60.2
of unsaturated amines

Cycloaddition reactions

[2 + 2], 82.2; 87.2; 95.2
[2 + 2 + 2], 97.1
[3 + 2], 61.1; 80.2; 94.1; 103.2
[4 + 2], 4.1; 4.2; 32.1; 65.2; 82.2; 101.1
[4 + 3], 51.3; 115.1
[6 + 4], 49.2
of alkynes, 97.1
of azomethine imines, 103.2

Cycloaddition reactions, (Continued)

of cyclenones and quinones, 5.3
of cyclic nitrones with alkenes, 94.1
of diazocarbonyl ylides, 80.2
of oxadienes, 101.1
cyclotrimerization of acetylenes, 68.1
Diels-Alder, acetylenes and alkenes, 4.2
Diels-Alder, imino dienophiles, 65.2
Diels-Alder, intramolecular, 32.1
Diels-Alder, maleic anhydride of enones of ketenes of nitrones and alkenes, 4.1; 44.2; 45.2; 82.2; 36.1
Kinugasa reaction, 114.2
Pauson-Khand, 40.1
photochemical, 44.2
retro-Diels-Alder reaction, 52.1; 53.2

Cycloalkenes, synthesis

by olefin ring-closing metathesis, 89.1

Cyclobutanes, synthesis

by ketene cycloaddition, 87.2
by thermal cycloaddition reactions, 12.1
from nitrile-stabilized carbanions
synthesis of, 44.2

Cycloheptadienes, from

divinylcyclopropanes, 41.1
polyhalo ketones, 29.2

Cyclooligomerization, 102.2

π-Cyclopentadienyl transition metal carbonyls, 17.1

Cyclopentenones

annulation, 45.1
synthesis, 40.1; 45.1; 104.2

Cyclopropanation, 57.1; 77.1

Cyclopropane carboxylates, from diazoacetic esters, 18.3

Cyclopropanes

from α-diazo carbonyl compounds, 26.2; 57.1
from carboxylic acid derivatives, 77.1
from metal-catalyzed decomposition of diazo compounds, 57.1
from nitrile-stabilized carbanions, 31.1
from tosylhydrazones, 23.3
from unsaturated compounds, methylene iodide and zinc-copper couple, 20.1; 58.1; 58.2

Cyclopropanols, synthesis of, 77.1

Cyclopropenes, synthesis of, 18.3

Cyclopropylamines, 77.1

Darzens glycidic ester condensation, 5.10; 31.1
DAST, 34.2; 35.3
Dealkoxycarbonylation of activated esters, 81.1
Deamination of aromatic primary amines, 2.7
Debenzylation, 7.5; 18.4
Decarboxylation of acids of esters, 9.5; 19.4; 81.1
Dehalogenation of α-halo acyl halides, 3.3
Dehydrogenation in Saegusa reaction in synthesis of ketenes in synthesis of acetylenes, 98.1; 3.3; 5.1
Demjanov reaction, 11.2
Dendrimer synthesis, 109.1
Deoxygenation of alcohols of vicinal diols, 77.2; 30.2; 77.2
Deprotonations by chiral lithium amides, 79.2
Deracemization, 118.3
Desoxybenzoins, conversion to benzoins, 4.5
Dess-Martin oxidation, 53.1
Desulfonylation reactions, 72.2
Desulfurization of α-(alkylthio)nitriles in alkene synthesis with Raney nickel, 30.2; 12.5
Desymmetrization, 104.1; 110.2
Diazo compounds, carbenoids derived from, 57.1; 75.2
Diazoacetic esters, reactions with alkenes alkynes, heterocyclic and aromatic compounds, 18.3; 26.2
α-Diazo carbonyl compounds conversion to carbonyl ylides in cyclopropanation reactions insertion and addition reactions preparation of, 80.2; 57.1; 26.2; 80.1; 57.1; 80.1
Diazomethane in Arndt-Eistert reaction reactions with aldehydes and ketones, 1.2; 8.8
Diazonium fluoroborates, synthesis and decomposition, 5.4

D

Diazonium salts

coupling with aliphatic compounds, 10.1; 10.2
in deamination of aromatic primary amines, 2.7
in Meerwein arylation reaction, 11.3; 24.3
in ring closure reactions, 9.7
in synthesis of biaryls and aryl quinones, 2.6

Diboration

application of, 105.2
geminal, 105.2
reagents, 105.2
vicinal, 105.2

1,4-Dicabonyl compounds from furans, 87.1

Dieckmann condensation, 1.9; 15.1

for synthesis of tetrahydrothiophenes, 6.9

Diels-Alder reaction

hetero-Diels-Alder reaction, 101.1
intramolecular, 32.1
retro-Diels-Alder reaction, 52.1; 53.2
with alkynyl and alkenyl dienophiles, 4.2
with cyclenones and quinones, 5.3
with imines, 65.2
with maleic anhydride, 4.1

Dihydro diols, 63.2

Dihydrofurans, 114.1

Dihydropyrans, 101.1

Dihydropyrimidine synthesis, 63.1

Dihydroxylation of alkenes

asymmetric, 66.2
hydrogen-bond-mediated, 76.1

Diimide, 40.2

Diketones

pyrolysis of diaryl, 1.6
reduction by acid in organic solvents, 22.3
synthesis by acylation of ketones, 8.3
synthesis by alkylation of β-diketone dianions, 17.2
synthesis by the Stetter Reaction, 106.2

Dimethyl sulfide, in oxidation reactions, 39.3

Dimethyl sulfoxide, in oxidation reactions, 39.3

Diols

deoxygenation of, 30.2
chiral, 105.3
oxidation of, 2.8

1,3-Diol monoesters from β-hydroxy

ketones, 86.2

Dioxetanes, 20.2

Dioxiranes, 61.2; 69.1

Dioxygenases, 63.2

1,3-Dipoles, 94.1

Dirhodium catalysts, 75.2

Disrotation, 117.3

Divinyl-aziridines, -cyclopropanes -oxiranes, and -thiiranes rearrangements of, 41.1

Doebner reaction, 1.8

Dynamic kinetic resolution, 118.3

E

Eastwood reaction, 30.2

Elbs reaction, 1.6; 35.2

Electrocyclization, 104.2; 117.3

Electrophile-nucleophile coupling, 103.3

Electrophilic

amination, 72.1
fluorination, 69.2

Enamines, reaction with quinones, 20.3

activation of catalytic enantioselctive Michael reactions, 90.1

Enantioselective

1,4-additions, 118.1
aldol reactions, 67.1
allylation and crotylation, 73.1
boronic acid Mannich reactions, 83.2
catalysis, 104.1
deprotonation, 79.2
Favorskii reaction, 100.4
halofunctionalization of alkenes, 105.1
hydroamination of alkenes, 88.1
hydroformylation, 107.1
hydrofunctionalization of alkenes, 100.3
hydrogenation of heteroaromatics, 96.1
Michael reactions, 90.1
ring-closing olefin metathesis, 89.1
perfluoroalkyl additions, 91.1
rhodium-catalyzed 1,4-additions of organoboranes to electron-deficient alkenes, 93.1

Ene reaction, in photosensitized oxygenation, 20.2

Enolates

α-Arylation, 76.2

Enolates: (Continued)

Fluorination of, 69.2
α-Hydroxylation of, 62.1
in directed aldol reactions, 28.3; 46.1; 51.1
rhodium intermediates in rhodium-catalyzed 1,4-additions addition to electron-deficient alkenes, 93.1

Enone cycloadditions, 44.2

1, n-Enyne cycloisomerizations, 92.1

Enzymatic reduction, 52.2

Enzymatic resolution, 37.1

Enzymes for dynamic kinetic resolution, 118.3

Epoxidation

of alkenes, 61.2; 74.3
of allylic alcohols, 48.1
with organic peracids, 7.7

Epoxide isomerizations, 29.3

Epoxide

carbonylation, 86.1
deoxygenation of, 111.1
formation, 48.1; 61.2; 74.3
meso, 110.2
migration, 60.1
reduction of, 111.1
ring expansion, 86.1
ring opening, 110.2; 111.1
trifluoroalkylation of, 91.1

Esters

acylation with acid chlorides, 1.9
alkylation of, 9.4
alkylidenation of, 43.1
cleavage via S 2-type dealkylation N, 24.2
cyclopropanation of, 77.1
dealkoxycarbonylation of, 81.1
dimerization, 23.2
glycidic, synthesis of, 5.10
hydrolysis, catalyzed by pig liver esterase, 37.1
β-hydroxy, synthesis of, 1.1; 22.4
β-keto, synthesis of, 15.1
reaction with organolithium reagents, 18.1
reduction of, 8.1; 71.1
synthesis from diazoacetic esters, 18.3
synthesis by Mitsunobu reaction, 42.2

Ethers, synthesis by Mitsunobu reaction, 42.2

Evans-Tishchenko reaction, 86.2
Exhaustive methylation, Hofmann, 11.5
Extrusion reactions, 78.3; 109.1
Favorskii rearrangement, 11.4
Ferrocenes, 17.1
Ferrocene-based catalysts for catalytic enantioselective Michael reactions, 90.1
Fischer carbene complexes, 70.2
Fischer indole cyclization, 10.2
Fluorinating agents, electrophilic, 69.2
Fluorination of aliphatic compounds of carbonyl compounds of heterocycles, 2.2; 21.1; 21.2; 34.2; 35.3; 69.2; 69.2; 69.2
Fluorination by DAST by N-F reagents by sulfur tetrafluoride catalytic, enantioselective electrophilic nucleophilic, 35.3; 69.2; 21.1; 34.2; 100.12; 104.3; 104.3
Formylation by hydroformylation of alkylphenols of aromatic hydrocarbons of aromatic compounds of non-aromatic compounds, 56.1; 28.1; 5.6; 49.1; 56.2
Free radical additions to alkenes and alkynes to form carbon-heteroatom bonds to alkenes to form carbon-carbon bonds deoxygenations, 111.1; 13.4; 13.3; 77.2
Freidel-Crafts catalysts, in nucleoside synthesis, 55.1
Friedel-Crafts reaction, 2.4; 3.1; 5.5; 18.1
Friedländer synthesis of quinolines, 28.2
Fries reaction, 1.11
Furans, oxidative cleavage, 87.1
Gattermann aldehyde synthesis, 9.2
Gattermann-Koch reaction, 5.6
Germanes, addition to alkenes and alkynes, 13.4
Glycals fluorination of, 69.2
transformation into glycosyl derivatives, 62.4

G

Glycosides, synthesis of, 64.2

Glycosylating agents, 68.2

Glycosylation

on polymer supports, 68.2
with catalyst control, 100.13
with sulfoxides and sulfinates, 64.2

Glycidic esters, synthesis and reactions of, 5.10

Gold catalysis, 92.1

Gold complexes with alkynes, alkenes, and arenes, 92.1

Goldberg arylation, 85.1

Gomberg-Bachmann reaction, 2.6; 9.7

Grundmann synthesis of aldehydes, 8.5

H

Halides, displacement reactions of, 22.2; 27.2

Halide-metal exchange, 58.2; 91.1

Halides, synthesis

from alcohols, 34.2
by chloromethylation, 1.3
from organoboranes, 33.1
from primary and secondary alcohols, 29.1

Haller-Bauer reaction, 9.1

Halocarbenes, synthesis and reactions of, 13.2

Halocyclopropanes, reactions of, 13.2

Halogenation, 105.1

Halogen-metal exchange, 100.2

Halogen-metal interconversion reactions, 6.7

α-Halo ketones, rearrangement of, 11.4

Halosilanes, 75.3

α-Halo sulfones, synthesis and reactions of, 25.1; 62.2

Hauser–Kraus annulations, 107.2

Heck reaction, 27.2

intramolecular, 60.2

Helicenes, synthesis by photocyclization, 30.1

Heteroarenes, 96.1

Heteroaryl amines, 85.1

Heteroaryl silanes, 75.3

Heteroatom-substituted cyclopropanes, 77.1

Heterocumulenes

cycloadditions with, 97.1

N

N-Heterocycles

by intramolecular hydroamination of amino alkenes, 88.1
by olefin ring-closing metathesis, 89.1
by vinyl and aryl azide cyclizations, 92.2
carbenes (NHCs), 106.2
from nitrogen-centered radicals, 108.1
lithiation-substitution of, 100.5

O

O-Heterocycles, synthesis by olefin ring-closing metathesis, 89.1

H

Heterocycles

synthesis by cycloaddition, 97.1
synthesis by extrusion, 109.1
synthesis by enyne cyclo-isomerizations, 92.1
synthesis by olefin ring-closing metathesis, 89.1
synthesis by rearrangement, 114.1

Heterocyclic aromatic systems, lithiation of, 26.1

Heterocyclic bases

amination of, 1.4; 85.1
in nucleosides, 55.1

Heterodienophiles, 53.2

Hilbert-Johnson method, 55.1

Hoesch reaction, 5.9

Hofmann elimination reaction, 11.5; 18.4

Hofmann reaction of amides, 3.7; 3.9

Homocouplings mediated by Cu, Ni, and Pd, 63.3

Homogeneous hydrogenation catalysts, 24.1

Homologation, 105.3

Hunsdiecker reaction, 9.5; 19.4

Hydration of alkenes, dienes, and alkynes, 13.1

Hydrazoic acid, reactions and generation of, 3.8

Hydroacylation, 96.2; 100.3

Hydroalkylation, 100.3

Hydroamination of alkenes, alkynes, dienes and allenes

Hydroarylation

of alkynes, 103.1

Hydroboration, 13.1

Hydrocarbamoylation, 96.2

Hydrocyanation

of alkenes and alkynes, 75.1
of conjugated carbonyl compounds, 25.3

Hydroesterification, 96.2

Hydroformylation, 56.1; 107.1

Hydrofunctionalization of alkenes

by hydrogen-atom transfer, 100.7
copper-catalyzed, 100.3

Hydrogen borrowing, 118.2

Hydrogen cyanide, 25.3; 75.1

Hydrogenation catalysts, homogeneous, 24.1

Hydrogenation of C=N functions, 74.1

Hydrogenation of esters, with copper chromite and Raney nickel, 8.1

Hydrohalogenation, 13.4

Hydrosilylation, 75.3

Hydroxyaldehydes, aromatic, 28.1

α-Hydroxyalkylation of activated olefins, 51.2

Hydroxycyclopropanes, 77.1

α-Hydroxy ketones

rearrangement, 62.3
synthesis of, 23.2

Hydroxylation

of enolates, 62.1
of ethylenic compounds with organic peracids, 7.7

Hydrozirconation of alkynes, 113.2

Hypervalent iodine reagents, 54.2; 57.2

I

Imidates, rearrangement of, 14.1

Imines, additions of allyl, allenyl, propargyl stannanes, 64.1

additions of cyanide, 70.1
addition of perfluoroalkyl carbanions, 91.1
as dienophiles, 65.2
catalytic asymmetric hydrogenation, 74.1
cycloadditions, 95.2
formation by twofold extrusion reactions, 78.3
synthesis, 70.1
synthesis by hydroamination of allenes

Iminium ions, 39.2; 65.2; 75.4; 90.1

Addition of perfluoralkyl carbanions, 91.1

Imino Diels-Alder reactions, 65.2

Indole synthesis

by catalyzed cyclization with alkenes, 76.3
by catalyzed cyclization with alkynes, 76.3
by Nenitzescu reaction by reaction with TosMIC by reductive cyclization by styrenyl azide cyclization −, 20.3; 57.3; 111.2; 92.2
Intramolecular C H insertion, 80.1
Intramolecular cycloaddition of oxadienes, 101.1
Ionic hydrogenation, 71.1
Iridium alkylation, 99.2
Iron-catalyzed cross-coupling reactions, 83.1
Iron(III) acetylacetonate (Fe(acac) ), 83.1
Isocyanides in the Passerini reaction in the Ugi reaction sulfonyl methyl, reactions of, 65.1; 57.3
Isoquinolines, synthesis of, 6.2; 6.3; 6.4; 20.3
Isoxazolines, synthesis by [3 + 2]dipolar cycloadditions with alkenes, 94.1
Jacobsen reaction, 1.12
Japp-Klingemann reaction, 10.2
Julia-Kocienski reaction, 95.1
Katsuki-Sharpless epoxidation, 48.1
Ketene cycloadditions, 45.2; 82.2
Ketenes and ketene dimers, synthesis of asymmetric cycloadditions cycloadditions, 3.3; 45.2; 87.2; 82.2; 45.2; 95.2
Ketimines, 99.1
α-Ketol rearrangement, 62.3
α-Keto esters as donors in catalytic enantio- selective Michael reactions, 90.1
Ketones acylation of alkylidenation of Baeyer-Villiger oxidation of cleavage of non-enolizable comparison of synthetic methods conversion to amides conversion to fluorides cyclic, synthesis of cyclization of divinyl ketones perfluoroalkylation of reaction with diazomethane reduction to aliphatic compounds reduction by alkoxyaluminum hydrides organosilanes, 8.3; 43.1; 9.3; 43.3; 9.1; 18.1; 3.8; 11.1; 78.1; 34.2; 35.3; 2.4; 23.2; 45.1; 91.1; 8.8; 4.8; 34.1; 71.1
reduction in anhydrous organic solvents, 22.3
synthesis by oxidation of alcohols, 6.5; 39.3
synthesis from acid chlorides and organo-metallic compounds, 8.2; 18.1
synthesis from organoboranes, 33.1
synthesis from organolithium reagents and carboxylic acids, 18.1
synthesis from α,β-unsaturated carbonyl compounds and metals in liquid ammonia, 23.1

K

Kindler modification of Willgerodt reaction, 3.2

Kinetic resolution

of alcohols and amines, 104.1
of chiral aminoalkenes

Kinugasa reaction, 114.2

Knoevenagel condensation, 1.8; 15.2; 57.3

Koch-Haaf reaction, 17.3

Kornblum oxidation, 39.3

Kostaneki synthesis of chromanes, flavones and isoflavones, 8.3

Krapcho dealkoxycarbonylation, 81.1

Kulinkovich cyclopropanation, 77.1

L

Lactams −

by intramolecular C H insertion, 80.1
from cyclic ketones, 78.1
by cycloaddition of vinylketene
unsaturated, by olefin ring-closing metathesis, 89.1

β-Lactams, synthesis of, 9.6; 26.2; 82.1; 82.2; 87.2; 95.2; 114.2

Lactones −

by intramolecular C H insertion, 80.1
unsaturated, by olefin ring-closing metathesis, 89.1

β-Lactones, by ketene cycloadditon, 82.2; 87.2

by ring expansion of epoxides, 86.1
synthesis and reactions of, 8.7

δ-Lactones by ring expansion of epoxides, 86.1

γ-Lactones by ring expansion of epoxides, 86.1

Leuckart reaction, 5.7

Lithiation

of allylic and benzylic systems, 27.1
by halogen-metal exchange, 6.7
heteroatom facilitated, 26.1; 47.1
of heterocyclic and olefinic compounds, 26.1
of N-heterocycles, 100.5
with chiral lithium amides, 79.2

Lithioorganocuprates, 19.1; 22.2; 41.2

Lithium aluminum hydride reductions, 6.2

chirally modified, 52.2

Lithium dialkylamides, 79.2

Lossen rearrangement, 3.7; 3.9

M

Macrocycles synthesis

by alkyne metathesis, 102.2
by olefin ring-closing metathesis, 89.1

Mannich reaction, 1.10; 7.3; 75.4; 83.2

Matteson reaction, 105.3

McMurry coupling reaction, 82.1

Meerwein arylation reaction, 11.3; 24.3

Meerwein-Ponndorf-Verley reduction, 2.5

Mercury hydride method to prepare radicals, 48.2

Metal acetylides, 100.4

Metal-catalyzed reactions

hydroacylation hydroamination of alkenes hydrocyanation enantioselective Michael reactions vinyl azide cyclizations, 96.2; 88.1; 75.1; 90.1; 92.2

Metalations with organolithium compounds, 8.6; 26.1; 27.1

Metallaphotoredox catalysis, 100.8

Metallocarbenes

conversion to carbonyl ylides −, 80.2
insertion in C H bonds, 80.1

Metathesis

alkyne, 102.2
olefin ring-closing, 89.1

Methylenation of carbonyl groups, 43.1

Methylenecyclopropane

hydroamination of, 88.1
in cycloaddition reactions, 61.1

Methylene-transfer reactions, 18.3; 20.1; 58.1

Meyer–Schuster rearrangement, 115.2

Michael reaction, 10.3; 15.1; 15.2; 19.1; 20.3; 46.1; 47.2; 90.1

Microbiological oxygenations, 63.2

Microwave irradiation in

olefin ring-closing metathesis reactions, 89.1
enantioselective Michael reactions, 90.1

Mitsunobu reaction, 42.2

Moffatt oxidation, 39.3; 53.1

Molybdenum-catalyzed allylic alkylation, 84.1

Morita-Baylis-Hillman reaction, 51.2

Mukaiyama aldol reaction, 98.2

Multicomponent reactions, 117.1

N

Nagata reaction, 25.3

N-alkylation, 118.2

Natural product synthesis, 98.2; 102.1; 102.2; 114.3

Nazarov cyclization, 45.1; 117.3

Neber rearrangement, 78.2

Nef reaction, 38.3

Negishi reaction, 100.1

Nenitzescu reaction, 20.3

Nicholas Reaction, 103.3

Nitrenium ion intermediates in vinyl and aryl azide cyclizations, 92.2

Nitriles

cycloadditions with, 97.1
cyclopropanation of, 77.1
formation from aldehydes alkenes and alkynes α-cyano esters oximes organoboranes, 78.1; 75.1; 81.1; 35.2; 33.1
α,β-unsaturated by elimination of selenoxides, 44.1
perfluoroalkylation of, 91.1

Nitrile-stabilized carbanions

alkylation and arylation of, 31.1

Nitroamines, 20.4

Nitro alkenes, as acceptors and donors in catalytic enantioselective Michael reactions, 90.1

Nitro compounds, conversion to carbonyl compounds, 38.3

Nitro compounds, synthesis of, 12.3

Nitrogen-centered radicals, 108.1
Nitrone-olefin cycloadditions, 36.1; 94.1
Nitrones, perfluoralkylation of, 91.1
Nitrosation, 2.6; 7.6
Nitroxide-catalyzed oxidations, 74.2
Norbornene, hydroamination of, 88.1
Nucleosides, synthesis of, 55.1
Olefin formation by reductive elimination of β-hydroxy sulfones by twofold extrusion reactions by ring-closing metathesis, 72.2; 78.3; 89.1
Olefins hydroamination of hydrocyanation of hydroformylation of metathesis of oxidation of perfluoroalkylation of, 88.1; 75.1; 106.1; 84.2; 91.1
Oligomerization of 1,3-dienes, 19.2
Oligosaccharide synthesis on polymer support, 68.2
Oppenauer oxidation, 6.5
Organoboranes formation of carbon-carbon and carbon- heteroatom bonds from in allylation of carbonyl compounds in boronic acid Mannich reactions in cross-coupling reactions isomerization and oxidation of reaction with anions of α-chloro nitriles rhodium-catalyzed additions to electron-deficient alkenes, 33.1; 73.1; 83.2; 79.1; 13.1; 31.1; 93.1
Organocatalysts, 96.1; 100.12; 100.13; 106.2
Organochromium reagents addition to carbonyl compounds addition to imines, 64.3; 67.2; 67.2
Organohypervalent iodine reagents, 54.2; 57.2
Organometallic compounds coupling reactions with electrophiles enantioselective addition of of aluminum, 83.1; 118.1; 25.3
of boron, 100.15
of chromium, 64.3; 67.2
of copper, 19.1; 22.2; 38.2; 41.2
of lithium, 6.7; 8.6; 18.1; 27.1
of magnesium and zinc, 100.2
of magnesium, zinc, and cadmium, 8.2
of palladium, 27.2
of silicon, 37.2
of tin, 50.1; 64.1; 111.1
of zinc, 1.1; 20.1; 22.4; 58.2
of zirconium, 118.1

O

Organonitriles, 75.1

Organosilane, 102.1

Organosilanols, 75.3

Organosilicon hydride reductions, 71.1

Organotrifluoroborates, in cross-coupling reactions, 79.1

Organozirconocenes, 113.2

Orthogonal reactivity, 97.2

Osmium tetroxide dihydroxylation

asymmetric, 66.2
hydrogen-bond directed, 76.1

Overman rearrangement of allylic imidates, 66.1

Oxadienes, 101.1

Oxazaborolidine catalysts for enantio- selective Michael reactions, 90.1

1,3-Oxazine-2,4-diones from epoxides, 86.1

1,3-Oxathiolan-2-ones from epoxides, 68.1

Oxidation

by dioxiranes, 61.2; 69.1
by oxoammonium and nitroxide catalysts, 74.2
by photooxygenation, 20.2
in Saegusa reaction, 98.1
of alcohols and polyhydroxy compounds, 6.5; 39.3; 53.1
of aldehydes and ketones Baeyer-Villiger reaction, 9.3; 43.3
of amines, phenols, aminophenols diamines, hydroquinones, and halophenols, 4.6; 35.2
of enolates and silyl enol ethers, 62.1
of furans, 87.1
of furfuryl alcohols, 87.1
of α-glycols, α-amino alcohols, and polyhydroxy compounds by periodic acid, 2.8
of organoboranes, 13.1
of phenolic compounds, 57.2
with hypervalent iodine reagents, 54.2
with peracids, 7.7
with selenium dioxide, 5.8; 24.4

Oxidative decarboxylation, 19.4

Oximes

conversion to α-amino ketones, 78.2
conversion to 2H-azirines, 78.2
formation by nitrosation, 7.6

Oxoammonium-catalyzed oxidation, 74.2

Oxochromium(VI)-amine complexes, 53.1

Oxo process, 56.1

Oxyamination, 108.2

Oxygenation of arenes by dioxygenases, 63.2

P

Palladium-catalyzed

amination of aryl halides, 100.14
arylation of enolates, 76.2
C–H functionalization, 117.1
cross-coupling of organostannanes organotrifluoroborates terminal alkynes, 50.1; 79.1; 116.1
enantioselective Michael reactions, 90.1
indole synthesis by cyclization, 76.3
oxidation of alkenes, 84.2
vinylic substitution, 27.2

Palladium intermediates in Heck reactions, 60.2

Passerini reaction, 65.1

Pauson-Khand reaction to prepare cyclopentenones, 40.1

Payne rearrangement, 60.1

Pechmann reaction, 7.1

Peptides, synthesis of, 3.5; 12.4; 97.2

Peracids, epoxidation and hydroxylation with, 7.7

in Baeyer-Villiger oxidation, 9.3; 43.3

Perfluoroalkyl organometallic reagents, 91.1

Perfluoroalkylations, 91.1

Periodic acid oxidation, 2.8

Perkin reaction, 1.8

Persulfate oxidation, 35.2

Petasis borono-Mannich reaction, 83.2

Peterson olefination, 38.1

Phase-transfer catalysis

of enantioselective Michael reactions, 90.1

Phenanthrenes, synthesis by photocyclization, 30.1

Phenols, dihydric from phenols, 35.2

oxidation of, 57.2
synthesis from Fischer carbene complexes, 70.2

Phosphinic acids, synthesis of, 6.6

Phosphonic acids, synthesis of, 6.6

Phosphonium salts

halide synthesis, use in, 29.1
synthesis and reactions of, 14.3

Phosphorus compounds, addition to carbonyl group, 6.6; 14.3; 25.2; 36.2

addition reactions at imine carbon, 36.2

Phosphorus-containing heterocycles synthesis

by olefin ring-closing metathesis, 89.1

Phosphoryl-stabilized anions, 25.2

Photochemical cycloadditions, 44.2

Photocyclization of stilbenes, 30.1

of styrenyl azides, 92.2

Photooxygenation of olefins, 20.2

Photoreduction, 77.2

Photosensitizers, 20.2

Piancatelli Reaction, 104.2

Pictet-Spengler reaction, 6.3; 114.3

Pig liver esterase, 37.1

Pinacols, by McMurry reaction, 82.1

Polonovski reaction, 39.2

Polyalkylbenzenes, in Jacobsen reaction, 1.12

Polycyclic aromatic compounds, synthesis by photocyclization of stilbenes, 30.1

Polyene synthesis, 109.1

Polyhalo ketones, reductive dehalogenation of, 29.2

Pomeranz-Fritsch reaction, 6.4

Prévost reaction, 9.5

Propargylic alcohols, 115.2

Propargylium-cobalt complexes

reductive coupling, 103.3

Pschorr synthesis, 2.6; 9.7

Pummerer reaction, 40.3

Pyranones from furan oxidation, 87.1

Pyrazolines, intermediates in diazoacetic ester reactions, 18.3

Pyridinium chlorochromate, 53.1

Pyrolysis

of amine oxides, phosphates, and acyl derivatives of ketones and diketones for synthesis of ketenes of xanthates, 11.5; 1.6; 3.3; 12.2
Pyrrole synthesis by reductive cyclization by vinyl azide cyclization, 111.2; 92.2
Pyrrolidines, by aza-Cope/Mannich reaction, 75.4
Pyrrolines, 114.1
Quaternary ammonium N-F reagents salts, rearrangements of, 69.2; 18.4
Quinolines, synthesis of by Friedländer synthesis by Skraup synthesis, 28.2; 7.2
Quinones acetoxylation of diene additions to synthesis from Fischer carbene complexes synthesis of synthesis of 5-hydroxyindoles, 19.3; 5.3; 70.2; 4.6; 20.3
Radical addition, allylation, vinylation, 110.1
Radical formation and cyclization, 48.2; 108.1
Radical-mediated alcohol deoxygenation, 77.2
Ramberg-Bäcklund rearrangement, 25.1; 62.2
Rearrangements allylic trihaloacetamidate anion-assisted sigmatropic Beckmann Brook Chapman Claisen Cloke–Wilson Cope Curtius divinylcyclopropane Favorskii Lossen Meyer–Schuster Ramberg-Bäcklund Smiles, 66.1; 43.2; 11.1; 35.1; 102.1; 14.1; 18.2; 2.1; 22.1; 114.1; 22.1; 41.1; 43.2; 3.7; 3.9; 41.1; 11.4; 3.7; 3.9; 115.2; 25.1; 62.2; 18.2
Sommelet-Hauser, 18.4
Stevens, 18.4
vinylcyclopropane-cyclopentene, 33.2
[2,3] Wittig, 46.2

R

Reduction

of acid chlorides to aldehydes, 4.7; 8.5
of aromatic compounds, 42.1
of benzils, 4.5
of ketones, enantioselective, 52.2
of O-thioacyl derivatives, 77.2
Clemmensen, 1.7; 22.3
desulfurization, 12.5
with diimide, 40.2
by dissolving metal, 42.1
by homogeneous hydrogenation catalysts, 24.1
by hydrogenation of esters with copper chromite and Raney nickel, 8.1
hydrogenolysis of benzyl groups, 7.5
by lithium aluminum hydride, 6.10
by Meerwein-Ponndorf-Verley reaction chiral, 2.5; 52.2
by metal alkoxyaluminum hydrides, 34.1; 36.3
by organosilanes, 71.1
of mono- and polynitroarenes, 20.4
of olefins by diimide, 40.2
of α,β-unsaturated carbonyl compounds, 23.1
by samarium(II) iodide, 46.3
by Wolff-Kishner reaction, 4.8

Reductive alkylation, synthesis of amines, 4.3; 5.7

Reductive amination of carbonyl compounds, 59.1; 71.1

Reductive coupling of carbonyl compounds, 82.1

Reductive cyanation, 57.3

Reductive cyclization, 111.2

Reductive desulfonylation, 72.2

Reductive desulfurization of thiol esters, 8.5

Reformatsky reaction, 1.1; 22.4

Regitz deformylation diazo transfer, 80.1

Reimer-Tiemann reaction, 13.2; 28.1

Reissert reaction, 70.1

Resolution of alcohols, 2.9

Retro-Diels-Alder reaction, 52.1; 53.2

Rhodium-catalyzed −

C H insertion, 80.1
carbonyl ylide formation, 80.2
cyclopropanation, 57.1
1,4-additions of organoboranes, 93.1

Ring-closing metathesis, 89.1

Ritter reaction, 17.3

Rosenmund reaction for synthesis of arsonic acids, 2.10

Rosenmund reduction, 4.7

S

Saegusa reaction, 98.1

Samarium(II) iodide, 46.3

Sammes annulations, 107.2

Sandmeyer reaction, 2.7

Saturated carbon frameworks, 113.1

Schiemann reaction, 5.4

Schmidt reaction, 3.8; 3.9; 78.1

Selenium dioxide oxidation, 5.8; 24.4

Seleno-Pummerer reaction, 40.3

Selenoxide elimination, 44.1

Seven-membered rings, 115.1

Shapiro reaction, 23.3; 39.1

Silanes

addition to olefins and acetylenes, 13.4
electrophilic substitution reactions, 37.2
oxidation of, 69.1
reduction with, 71.1; 77.2

Silanolate salts, 75.3

Sila-Pummerer reaction, 40.3

Siliconates, 75.3

Silicon-based cross-coupling, 75.3

Silicon-containing heterocycles synthesis

by ring-closing metathesis, 89.1

Silver salt catalysis, 92.1

Silyl carbanions, 38.1

Silyl compounds, cross-coupling of, 75.3

Silyl enol ethers, α-hydroxylation of, 62.1

in catalytic, enantioselective Michael reactions, 90.1

Silyl migration, 102.1

Simmons-Smith reaction, 20.1; 58.1

Simonini reaction, 9.5

Singlet oxygen, 20.2; 87.1

Skraup synthesis, 7.2; 28.2

Smiles rearrangement, 18.2; 95.1

Solid-Phase synthesis

of cyclic alkenes by olefin ring-closing metathesis, 89.1

Solid-Phase synthesis: (Continued) of dihydropyrans of indoles, 101.1; 76.3

Sommelet-Hauser rearrangement, 18.4

Sommelet reaction, 8.4

Sonogashira reaction, 116.1

S 1 reactions of aromatic systems, 54.1

Staudinger-Pfenniger reaction, 78.3

Staudinger synthesis of β-lactams, 82.2; 95.2

Staunton–Weinreb annulations, 107.2

Stereocenters, contiguous, 110.2

Stereocontrolled synthesis, 118.3

Stereoselective N-alkylation, 118.2

Stereoselectivity, 98.2; 108.1

Stereospecific displacement, 105.3

Stetter reaction of aldehydes with olefins, 40.4; 106.2

Stevens rearrangement, 18.4

Strecker reaction, catalytic asymmetric, 70.1

Stilbenes, photocyclization of hydroamination of, 30.1; 88.1

Stille reaction, 50.1

Stobbe condensation, 6.1

Styrenyl azide cyclizations, 92.2

Substitution allylic of N-heterocycles with organocopper reagents, 99.2; 100.5; 22.2; 41.2

Succinic anhydrides from epoxides, 86.1

Sugars, synthesis by glycosylation with sulfoxides and sulfinates, 64.2

Sulfide reduction of nitroarenes, 20.4

Sulfonation of aromatic hydrocarbons and aryl halides, 3.4

Sulfur-containing heterocycles synthesis by olefin ring-closing metathesis, 89.1

Supramolecular compounds synthesis by olefin ring-closing metathesis, 89.1

Suzuki-Miyaura cross-coupling, 79.1; 100.9

Swern oxidation, 39.3; 53.1

T

Tamura annulations, 107.2

Tandem reactions − C N bond formation heterocycloaddition reactions, 118.2; 101.1

Tandem olefin metathesis reactions, 89.1

Tetrahydroisoquinolines, synthesis of, 6.3
Tetrahydrothiophenes, synthesis of, 6.9
1,2,4-Thiadiazoles as extrusion intermediates, 78.3
Thia-Payne rearrangement, 60.1
Thiazoles, synthesis of, 6.8
Thiele-Winter acetoxylation of quinones, 19.3
Thioacylation of alcohols, 77.2
Thiocarbonates, synthesis of, 17.3; 77.2
Thiocyanation of aromatic amines, phenols and polynuclear hydrocarbons, 3.6
Thiophenes, synthesis of, 6.9
Thiourea catalysts in enantioselective Michael reactions in Pictet-Spengler reactions, 90.1; 114.3
Thorpe-Ziegler condensation, 15.1
Tiemann reaction, 3.9
Tiffeneau-Demjanov reaction, 11.2
Tin(II) enolates, 46.1; 110.1
Tin hydride method to prepare radicals, 48.2
Tipson-Cohen reaction, 30.2
Tishchenko reaction, 86.1
Titanium, low valent species in coupling, 82.1
Tosylhydrazones, 23.3; 39.1
Tosylmethyl isocyanide (TosMIC), 57.3
Transfer hydrogenation, 100.6
Transition metal complexes as catalysts for alkyl-alkyl cross-coupling − C F bond formation − C H activation reactions − C H functionalization − C N bond formation cross-metathesis of alkenes cycloadditions dynamic kinetic resolution enantioselective hydrogenation enantioselective Michael reactions glycosylation hydroacylation hydroamination of alkenes hydroarylation of alkynes, 113.1; 104.3; 100.11; 100.10; 118.2; 106.1; 97.1; 118.3; 96.1; 90.1; 100.13; 96.2; 88.1; 103.1
Transmetallation reactions, 58.2; 100.2; 113.2
Transition-metal-mediated coupling, 117.2
Tributylstannane, in xanthate reduction, 77.2

Tricarbonyl(η -arene)chromium complexes, 67.2

Trihaloacetimidate, allylic rearrangements, 66.1

Trifluoroborates, in cross-coupling reactions, 79.1

Trifluoromethylation, 91.1

Trifluoromethyl carbanion, 91.1

Trifluoromethyllithium, 91.1

Trimerization, co-, acetylenic compounds, 68.1

Trimethylenemethane, [3 + 2] cycloaddition of, 61.1

Trimethylsilyl cyanide, 75.1

Tryptamines, 114.3

U

Ugi reaction

Ullmann reaction, 2.6; 14.1; 63.3; 85.1

Unsaturated compounds, synthesis

with alkenyl- and alkynylaluminum reagents, 32.2

V

Vilsmeier reaction, 49.1; 56.2

Vinylcyclopropanes, rearrangement to cyclopentenes, 33.2

Vinyl diazoacetates, 75.2

Vinyllithium reagents, from sulfonylhydrazones, 39.1

Vinylketenes

preparation of, 87.2
electrocyclization of, 87.2

Vinylogy, 98.2

Vinylsilanes, electrophilic substitution reactions of, 37.2

Vinylstannanes, 110.1

Vinyltrifluoroborates, 79.1

Vinyl substitution, catalyzed by palladium complexes, 27.2

von Braun cyanogen bromide reaction, 7.4

Vorbrüggen reaction, 55.1

W

Wacker oxidation, 84.2

Watanabe-Cenini-Söderberg reaction, 111.2

Willgerodt reaction, 3.2

Wittig reaction, 14.3; 31.1

[2,3]-Wittig rearrangement, 46.2

Wolff-Kishner reaction, 4.8

X

Xanthates

in the Barton-McCombie reaction, 77.2
synthesis and reactions of, 12.2; 77.2

Y

Ylides

in Stevens rearrangement, 18.4
in Wittig reaction, structure and properties, 14.3

Z

Zinc-copper couple, 20.1; 58.1; 58.2

Zinin reduction of nitroarenes, 20.4