March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 7th Edition (2013)
Appendix B. Classification of Reactions by Type of Compounds Synthesized
ACETALS
acetals + RM
10-64
aldehydes + alcohols
16-05
by transetherification
10-13
from dihalides
10-08
from hydroxy-ethers
14-06
ortho esters + RM
10-64
reductive cleavage of ortho esters
19-56
ACYLALS (DIESTERS)
aldehydes + anhydrides
16-06
ACYLOINS: See hydroxy-ketones
ALCOHOLS
addition of other organometallics to carbonyls
16-25
aldehydes + allylic silanes
16-51
alkenes + alcohols
15-33
alkenes + aldehydes or ketones
16-54
alkenes-oxymercuration
15-03
amides + organometallic compounds
16-82
amines + KOH
10-23
anhydrides + organometallic compounds
16-82
aromatics + carbonyls
11-12
arylation of ketones
11-12
boranes + CO; oxidation
18-23
boranes + CO; reduction
18-24
by the Cannizzaro reaction
19-81
by Wittig rearrangement
18-22
carboxylic esters + organometallics
16-82
cleavage of ethers
10-49
condensation of aldehydes
19-81
conjugate reduction
15-14
epoxides + organometallics
10-65
epoxides + silanes
10-55
from alcohols
10-17
from amines
10-23
from boranes
10-01
from boranes
12-27
from boranes
18-23
from boronates
18-23
from epoxides
10-65
from ethers
10-13
from silanes
10-16
Grignard addition to aldehydes or ketones
16-24
hydration of alkenes
15-03
hydrolysis of acetals and ketals
10-06
hydrolysis of alkyl halides
10-01
hydrolysis of inorganic esters
10-04
hydrolysis of sulfonate esters
10-04
hydrolysis of vinyl ethers
10-06
hydroxylation at aliphatic carbon
19-14
hydroxymethylation of arenes
11-12
organolithium addition to aldehydes or ketones
16-24
organometallics + oxygen
12-25
oxidation of boranes
12-27
oxidation of boranes
15-16
oxidation of boranes
18-23
oxidation of methylene
19-15
oxidation of silanes
10-16
radical addition to carbonyl compounds
16-56
rearrangement of ethers
18-22
rearrangement of peroxides
18-20
reduction of acyl halides
19-63
reduction of aldehydes or ketones
19-36
reduction of carbonyls with Grignard reagents
16-24
reduction of carboxylic acids
19-37
reduction of carboxylic esters
19-38
reduction of carboxylic esters
19-65
reduction of conjugated ketones
15-44
reduction of epoxides
19-35
reduction peroxides
19-60
ring expansion of amines
18-03
silanes + aldehydes or ketones
16-26
ALCOHOLS, ALLYLIC
addition of allylic organometallics to carbonyls
16-25
alkenes + formaldehyde
16-54
allylic silanes + aldehydes or ketones
16-26
deprotonation of epoxides
17-03
rearrangement of alkene-sulfoxides
18-35
ALDEHYDES
alkenes + aldehydes
15-33
alkyl halides + organoiron compounds
10-76
alkylation of aldehydes
10-68
alkylation of imines
10-68
alkylation reactions
10-67
and keto–enol tautomerism
12-03
aromatic compounds: Friedel–Crafts
11-18
arylation of aldehydes
13-14
boranes + MeO(ArS)CH2Li
18-24
by decarboxylation
12-40
by rearrangement of aldehydes
18-04
by the Wacker process
19-25
carbonylation of alkenes
15-37
carbonylation of aromatic compounds
11-18
carbonylation of hydrocarbons
12-33
formylation of aromatic compounds
11-18
from alkyl halides
10-64
from alkyl halides
10-76
from aryl imines
11-18
from dihydrooxazines
10-72
from dithianes
10-71
from dithioaldehydes
16-11
from organometallics
12-33
from oxazines
10-72
hydration of alkynes
15-04
hydroformylation
15-37
hydrolysis of acetals
10-05
hydrolysis of C=N compounds
16-02
hydrolysis of gem-dihalides
10-02
hydrolysis of nitro compounds
16-03
hydrolysis of vinyl ethers
10-06
hydrolysis of vinyl halides
10-04
Michael addition
15-24
oxidation of alcohols
19-03
oxidation of aryl methyl groups
19-18
oxidation of nitro compounds
19-21
oxidation of primary alkyl halides
19-20
oxidative cleavage of diols
19-07
oxidative cleavage of epoxides
19-07
ozonolysis of alkenes
19-09
reduction anhydrides
19-40
reduction nitriles
19-44
reduction of acid anhydrides
19-40
reduction of acyl halides
19-39
reduction of amides
19-41
reduction of carboxylic acids
19-40
reduction of carboxylic esters
19-40
ALDEHYDES, CONJUGATED
by aldol condensation
16-34
ALKANES
alcohols + RM
10-63
alkane addition to alkenes
15-18
alkenes + alkyl radicals
15-29
alkenes + diimide
15-12
alkenes + metals
15-12
alkenes + organometallics
15-21
alkyl halides + metals
10-56
alkyl halides + metals
10-57
alkyl halides + organocuprates
10-58
alkyl halides + RM (Li, Na, K)
10-57
alkyl halides + RM (other metals)
10-59
alkyl halides + silanes
10-55
Barton–McCombie reaction
19-58
by [2 + 2]-cycloaddition
15-63
by [3 + 2]-cycloaddition
15-59
by decarboxylation
12-40
cleavage of alkanes
12-47
cleavage of ketones
12-46
coupling of boranes
14-26
coupling of carboxylate salts
14-29
coupling of Grignard reagents
14-24
coupling of organocuprates
14-25
coupling of two alkanes
14-15
decarbonylation of aldehydes
14-32
decyanation
12-48
from alcohols
10-63
from alcohols
19-58
from alkanes
12-20
from alkanes
12-21
from alkyl halides
10-55–10-59
from alkyl halides
12-24
from alkylborates
10-59
from boranes
10-59
from nitriles
12-48
from organometallics
12-22
from organometallics
12-23
from organometallics
12-24
from S compounds
10-61
from S compounds
14-27
from silanes
10-55
Grignard reagents with metal compounds
14-24
homocoupling of organocuprates
14-24
hydrogen exchange
12-01
hydrogenation of alkenes
15-11
hydrogenation of alkynes
15-11
hydrogenation of aromatic compounds
15-13
inorganic esters + RM
10-61
insertion by carbenes
12-21
Kolbe reaction
14-29
pyrolysis of peroxides
17-37
radical addition to alkenes
15-29
radical coupling of alkanes
14-14
radical cyclization of alkenes
15-30
reduction dithianes
10-71
reduction of acyl halides
19-59
reduction of alcohols
19-54
reduction of alkenes and alkynes
15-12
reduction of alkyl halides
19-53
reduction of anhydrides
19-65
reduction of carbonyls to methylene
19-61
reduction of carboxylic esters
19-65
reduction of nitriles
19-66
reduction of nitro compounds
19-67
reduction of silanes
19-52
reduction of sulfonate esters
19-57
reduction of sulfur compounds
19-70
reduction of thioethers
14-27
reduction of thiols
14-27
reduction of thiols
19-70
reduction of xanthate esters
19-58
reductive cleavage of cyclopropanes
15-15
reductive cleavage of ethers
19-56
replacement of metals in RM by hydrogen
12-24
σ-bond rearrangements
18-38
sulfonate esters + metals
10-56
sulfonate esters + organocuprates
10-58
sulfur compounds + organometallics
10-61
via transmetallation
12-22
ALKENE-ALCOHOLS
rearrangement of alkene-ethers
18-35
ALKENE-ALDEHYDES
Claisen rearrangement
18-33
Cope rearrangement
18-32
rearrangement of allyl vinyl ethers
18-33
ALKENE-ALKYNES
addition of alkynes to alkynes
15-20
ALKENE-AMINES
rearrangement of alkene-ammonium salts
18-35
ALKENE-CARBOXYLIC ACIDS
Claisen rearrangement
18-33
rearrangement of alkene-esters
18-33
ALKENE-KETONES
Claisen rearrangement
18-33
rearrangement of allyl vinyl ethers
18-33
ALKENE-THIOETHERS
rearrangement of alkene sulfonium salts
18-35
ALKENES
aldehydes or ketones + active H compounds
16-38
alkane addition to alkynes
15-18
alkene addition\to alkenes
15-20
alkene metathesis
18-37
alkenes + aryl halides
13-10
alkenes + arylboronic acids
13-10
alkenes + aryldiazonium compounds
13-10
alkenes + carbenes
15-64
alkenes + carbocations
12-20
alkynes + alkyl halides + RM (M = metal)
15-22
alkynes + metals or metal hydrides
15-12
allylic esters + RM
10-60
allylic halides + metals
10-56
allylic silanes + esters
10-60
aryldiazonium salts + alkenes
13-26
base induced elimination of halosulfones
17-20
bis(decarboxylation) of dicarboxylic acids
19-13
by [2 + 2]-cycloaddition
15-63
by [3 + 2]-cycloaddition
15-59
by decarboxylation
12-40
by McMurry coupling
19-77
by migration of double bonds
12-02
by Peterson alkenylation
16-41
by the Diels–Alder reaction
15-60
by the ene reaction
15-23
by the Heck reaction
13-10
by the heteroatom Diels–Alder reaction
15-61
by the Horner–Wadsworth–Emmons reaction
16-44
by the Knoevenagel reaction
16-38
by the Ramberg–Bäcklund reaction
17-20
by the Sakurai reaction
15-26
by the Wittig reaction
16-44
cleavage of ethers
17-02
cleavage of vinyl ethers
17-02
conjugated addition of allylsilanes
15-26
deacyloxylation
19-59
decarbonylation of acyl halides
17-17
decarboxylation of hydroxy-carboxylic acids
17-26
dehydration of alcohols
17-01
dehydrogenation
19-02
deoxygenation of 1,2-diols
17-18
deprotonation of episulfides (thiiranes)
17-03
deprotonation of epoxides (oxiranes)
17-03
diazoalkanes + aldehydes
15-64
dimerization of alkyl halides
19-32
elimination (1,3-) of diols
17-25
elimination (1,3-) of haloamines
17-25
elimination (1,3-) of halohydrins
17-25
elimination (base) of ammonium salts
17-07
elimination (base) of ammonium salts
17-08
elimination (base) of halides
17-13
elimination (base) of sulfonate esters
17-06
elimination (base) of sulfonyl halides
17-14
elimination (base) of sulfonyl hydrazones
17-11
elimination of 1,2-dihalides
17-22
elimination of boranes
17-15
elimination of haloethers
17-24
enamines + boranes
15-16
esters + organometallics
10-60
extrusion from oxathiolanes
17-38
extrusion of CO from cyclic ketones
17-35
from alcohols
10-63
from alkenes
13-26
from alkyl halides
10-55
from allylic esters
10-60
from bis(xanthates)
17-18
from boranes
10-59
from carbenes
12-21
from dienes
18-37
from episulfones
16-48
from epoxides or thiiranes
17-03
from imines
16-44
from selenones
10-71
from silanes
10-55
hydroboration of alkynes
18-25
hydrogenation of alkynes
15-11
hydrogenation of aromatic compounds
15-13
isomerization of double bonds
15-01
ketones or aldehydes + bis(Grignards)
16-24
migration of boranes
12-02
migration of double bonds
12-02
nitrosation of aziridines
17-21
organometallics + ketones
16-25
organometallics + tosylhydrazones
16-38
other cycloaddition reactions
15-66
oxidative decarboxylation of carboxylic acids
19-12
Petasis alkenylation
16-45
protonolysis of vinyl boranes
18-25
protonolysis of vinyl boranes
18-26
pyrolysis of amine oxides (Cope)
17-09
pyrolysis of ammonium salts (Hofmann)
17-07
pyrolysis of esters
17-04
pyrolysis of hydroxy-alkenes
17-32
pyrolysis of sulfones
17-12
pyrolysis of sulfoxides
17-12
pyrolysis of thionocarbonates
17-19
pyrolysis of xanthates (Chugaev)
17-05
pyrolysis of β-lactones
17-26
rearrangement of dienes
18-39
reduction of enamines
19-67
reduction of hydrazones
19-61
reduction of thiiranes
19-35
reduction of thiophene derivatives
19-70
reduction of vinyl halides
19-53
reduction of vinyl imines
19-61
reductive coupling of aldehydes or ketones
19-77
reductive coupling of epoxides
19-35
sigmatropic carbon migration
18-30
sigmatropic H migration
18-29
silyl-organometallics + aldehydes or ketones
16-41
Tebbe alkenylation
16-45
vinyl boranes + halogen/base
18-25
vinyl halides + arylboronic acids
13-10
vinyl-cyclopropane rearrangement
18-31
vinyl-X + alkyl(aryl)boronic acids
12-15
Wagner–Meerwein rearrangement of alcohols
18-01
Wagner–Meerwein rearrangement of halides
18-01
ALKYNE-ALCOHOLS
addition of alkynes to carbonyls
16-25
ALKYNES
alkyl halides + alkyne anions
10-74
alkyl halides + propargylic RM
10-57
alkynes + aryliodonium salts
13-13
alkynes + boranes
18-26
aryl halides + alkyne-M (M = a metal)
13-13
aryl halides + alkynes
10-74
base-induced isomerization alkynes
12-02
dimerization of dihalides
19-32
elimination of alkenes
17-16
elimination of dihalo compounds (by base)
17-16
elimination of halides (by base)
17-13
from alkyl halides
10-74
from alkynes
10-74
hypervalent iodine + alkyne-M (M = a metal)
12-26
metathesis of alkynes
18-37
pyrolysis of bis(ammonium)salts
17-07
pyrolysis of thiirene dioxides
17-20
pyrolysis of ylids
17-10
Sonogashira coupling
13-13
Stephens–Castro coupling
13-13
ALLENES
base-induced rearrangement of halocyclopropanes
18-03
by Claisen rearrangement
18-33
by the Wittig reaction
16-44
Cope rearrangement of diynes
18-32
elimination of dihalides
17-22
propargylic esters + organocuprates
10-60
reduction of alkynes
19-53
ALLOPHANATES
carbamates + isocyanates
16-08
AMIDE–ESTERS
aziridines + amides
10-14
AMIDES
acyl halides + ammonia or amines
16-72
addition of organometallics to isocyanates
16-33
alcohols + cyanogen halides
16-09
aldehydes + ammonia + oxidant
14-11
alkanes + nitriles
14-12
alkenes + amides
15-09
alkenes + nitriles
16-91
alkyl halides + amides
10-41
amides + aldehydes
10-41
amides + amines
16-76
amines + CO + alkenes
15-36
amines + CO
12-53
amines + haloformates
10-53
amines + organoiron compounds
10-77
amines + vinyl esters
16-75
anhydrides + ammonia or amines
16-73
aromatic compounds + amides
11-22
aromatic compounds + hydroxamic acids
11-06
aromatic compounds + isocyanates
11-21
aryl halides + amides
10-41
aryl halides + amides
13-05
aryl halides, DMF and POCl3
11-21
by Beckmann rearrangement
18-17
by Michael addition
15-24
by Mitsunobu reaction
10-41
by reaction with nitrenes
12-13
by the Haller–Bauer reaction
12-46
by the Willgerodt reaction
19-84
carboxylic acids + amino-boranes
16-74
carboxylic acids and ammonia or amines
16-74
carboxylic esters + ammonia or amines
16-75
cleavage of ketones
12-46
condensation of methyl ketones
19-84
dealkylation of amides
19-73
from alcohols
10-41
from aromatic compounds
11-19
from N-halo amides
11-31
hydrolysis of isonitriles
16-97
hydrolysis of nitriles
16-04
imines + borane + CO
12-33
insertion of acyl nitrenes
12-13
insertion of diazo amides
12-21
ketenes + amines
15-08
ketones + HN3
18-16
ketones + −NH2
12-46
N-alkylation
10-41
N-arylation
10-41
nitriles + alcohols
16-91
nitriles + amines
16-21
oxidation of methylene in amines
19-17
oximes + halogenating or oxidizing agents
18-17
pyrolysis of imino esters
18-42
rearrangement of oximes
18-17
reduction of imides
19-64
Ritter reaction
16-91
transamidation
16-70
AMIDES, CONJUGATED
isocyanates + vinyl-M (metal)
15-22
AMIDINES
ketenimines + amines
15-08
nitriles + ammonia or amines
16-21
AMIDO-ALCOHOLS
alkenes + amides
15-52
AMINE OXIDES
oxidation of amines
19-29
AMINES
addition of organometallics to C=N compounds
16-31
addition of silanes to C=N
16-31
alkenes + amines or ammonia
15-08
alkyl halides + amines
10-31
alkylation of amines
10-31
alkylation of formamidines
10-71
alkylation of nitroso amines
10-71
allylic amination
12-12
amides + organometallic compounds
16-82
amination of active methylene compounds
12-12
amination of alkanes
10-39
amination of alkanes
12-12
amination of heterocycles
13-18
amination of methylene
19-16
amines + aryl halides
13-05
amines + diaryliodonium compounds
11-06
amines + diazo compounds
10-34
aminomethylation of aromatic compound
11-22
aromatic compounds + amide bases
13-18
aromatic compounds + aryl azides
11-06
aromatic compounds + haloamines
11-06
aromatic compounds + hydrazoic acid
11-06
aryl halides + amines
13-05
aryl halides + hydroxylamine-O-sulfonic acid
18-15
azides + haloboranes
12-32
aziridines + RM
10-66
boranes + ammonia + NaOCl
12-32
boranes + chloramine
12-32
by amidomethylation
11-22
by reaction with nitrenes
12-13
by the Stevens rearrangement
18-21
by transamination
10-33
Curtius rearrangement
18-14
cyclization of haloamines
18-40
dealkylation of amines
19-73
dehydrogenation
19-02
displacement of cyano
10-62
diynes + amines
15-08
enamines + boranes
15-16
from alcohols
10-31
from alcohols
10-32
from alkanes
10-39
from amides
18-13
from amines
10-31
from amines
10-33
from amines
10-34
from amines
10-71
from amino-ethers
10-64
from amino-nitriles
10-62
from ammonium salts
11-32
from boranes
10-31
from cyanohydrins
10-32
from ethers
10-32
from haloamines
10-31
from hydrazones
10-71
from hydroxylamines
13-32
from nitroamines
11-28
from nitrosamines
11-29
from organometallics
12-32
from phenols
11-22
from phenols
13-06
Hofmann rearrangement
18-13
Hofmann–Löffler reaction
18-40
hydrolysis of isocyanates
18-13
hydrolysis of isocyanates
18-15
hydrolysis of isocyanates
18-16
hydroxylamines + alkyl organometallics
12-32
imines + allylic silanes
16-51
insertion of nitrenes
12-13
Lossen rearrangement
18-15
Michael addition with N nucleophiles
15-31
phenols + amines or ammonia
13-06
Pictet–Spengler reaction
10-13
radical addition to C=N compounds
16-56
rearrangement of ammonium salts
13-31
rearrangement of ammonium salts
18-21
rearrangement of aryl hydroxylamines
13-32
reduction nitroso compounds
19-47
reduction of amides
19-64
reduction of amine oxides
19-68
reduction of amines
19-64
reduction of azides
19-50
reduction of azo compounds
19-74
reduction of azoxy compounds
19-74
reduction of C=N compounds
19-42
reduction of hydrazines
19-74
reduction of hydroxylamines
19-47
reduction of isocyanates
19-51
reduction of isothiocyanates
19-51
reduction of lactams
19-64
reduction of nitriles
19-43
reduction of nitro compounds
19-45
reduction of nitrosoamines
19-51
reduction oximes
19-48
reductive alkylation of aldehydes or ketones
16-17
Schmidt reaction
18-16
Sommelet–Hauser rearrangement
13-31
Stevens rearrangement
13-31
transamination
10-33
AMINO ACIDS
lactones + ammonia or amines
16-75
AMINO ALCOHOLS
alkenes + amines
15-52
epoxides + amines or ammonia
10-35
from amino epoxides
10-36
from isonitriles
10-40
from nitroalcohols
10-35
oxetanes + amines or ammonia
10-37
rearrangement of haloamines
18-10
reductive coupling of C=N with C=O
19-76
AMINO ALDEHYDES
aldehydes + C=N compounds
16-31
AMINO ESTERS
diazoesters + amines
15-64
AMINO ETHERS
aziridines + alcohols
10-14
AMINO KETONES
base-induced rearrangement of sulfonyl oximes
18-12
ketones + HCHO + amines
16-19
Mannich reaction
16-19
AMINO NITRILES
from amines
12-19
from cyanohydrins
10-32
HCN or cyanide + C=N compounds
16-53
AMINO THIOETHERS
alkenes + sulfonamides
15-55
alkenes + sulfonium salts + amines
15-55
AMINO THIOLS
episulfides + amines or ammonia
10-35
AMMONIUM SALTS
alkyl halides + amines
10-31
ANHYDRIDES
acyl halides + carboxylic acids
16-66
aldehydes + acyl peroxides
14-09
carboxylic acids + vinyl esters
16-67
dehydration of carboxylic acids
16-67
dehydration of dicarboxylic acids
16-67
ANHYDRIDES, ORGANIC–INORGANIC
anhydrides + mineral acids
16-68
ARENES
alkyl halides + ArM (Li, Na, K)
10-57
alkyl halides + aryl organometallics
10-57
alkyl halides + arylboronic acids
13-09
alkyl halides + organocuprates
10-58
alkyl halides + organometallics
13-17
aromatic compounds + active H compounds
13-17
aromatic compounds + acylperoxides
14-17
aromatic compounds + alcohols
11-11
aromatic compounds + alkenes
11-11
aromatic compounds + alkyl halides
11-11
aromatic compounds + carboxylic acids
14-19
aromatic compounds + ketones
11-12
aromatic compounds + peroxides
14-17
aryl halides + active methylene compounds
13-14
aryl halides + alkenes
13-10
aryl halides + alkenes
15-21
aryl halides + alkynes
15-21
aryl halides + organocuprates
10-58
aryl halides + RM (other metals)
10-59
aryl halides + trifluoroborates
13-09
aryl halides + vinylboronic acids
13-09
aryldiazonium salts + alkenes
13-26
aryldiazonium salts + alkyl organometallics
13-25
aryldiazonium salts + organometallics
13-25
by decarboxylation
12-40
by radical cyclization
15-30
coupling of aromatic compounds
11-15
cyclodehydration of carbonyl compounds
11-13
Friedel–Crafts alkylation
11-11
from alkylborates
10-59
from boranes
10-59
from ketones
11-13
hydrogen exchange
11-01
rearrangement of N-alkyl aryl amines
11-32
replacement of aryl nitro
13-29
α-halo ketones + organocuprates
10-58
AROMATIC COMPOUNDS
alkylation of heteroaryls
14-19
aromatic compounds + carbenes
15-64
aromatization of six-membered rings
19-01
cleavage of arenes
11-33
cleavage of aryl alkyl ethers
11-37
cyclization of ene–diynes
18-27
cyclotrimerization of alkynes
15-65
deamination of aromatic compounds
19-69
decarbonylation of aryl aldehydes
11-34
decarboxylation of aryl carboxylic acids
11-35
dehalogenation of aryl halides
11-39
dehydrogenation of cyclic alkanes
19-01
deoxygenation of aryl ethers
11-37
desulfonylation of aryl sulfonic acids
11-38
from aldehydes
11-34
from aromatic compounds
11-33
from aromatic compounds
18-28
hydrolysis of aromatic organometallics
11-41
protonation of aryl organometallics
11-41
pyrolysis of bicyclic dienones
17-28
reduction aryl diazonium salts
19-69
reduction of aryl halides
11-39
reduction of phenols
19-55
reduction of quinones
19-01
AZIDES
aldehydes + metal azides
16-78
alkenes + hydrazoic acid
15-10
alkenes + metal azides
15-53
amides + sulfonyl azides
12-11
from acyl halides
10-43
from alkyl halides
10-43
hydrazines + HONO or nitrosyl compounds
12-49
AZIDO ALCOHOLS
from epoxides
10-43
AZIDO AMIDES
from amides
12-11
AZIDO AMINES
from aziridines
10-38
AZIRIDINES
alkenes + alkyl azides
15-54
alkenes + halogen + haloamines
15-54
C=N compounds + sulfur ylids
16-47
extrusion of nitrogen from triazolines
17-34
form haloamines
10-31
from allene amides
15-09
from azido alcohols
10-43
from epoxides
10-36
from halo-azides
15-45
from hydroxy-amines
10-32
from imines
16-32
from triazolines
15-58
imines + diazo compounds
16-32
AZIRINES
alkynes + amino nitrenes
15-54
AZO COMPOUNDS
aryl amines + nitroso compounds
13-24
aryl diazonium salts + aromatic compounds
11-04
from aryldiazonium salts
13-28
oxidation of hydrazines
19-05
rearrangement of aryl triazenes
11-30
rearrangement of azoxy compounds
18-43
reduction of azoxy compounds
19-68
reduction of nitro compounds
19-80
Wallach rearrangement
18-43
AZOXY COMPOUNDS
from alkyl halides
10-45
nitroso compounds + hydroxylamines
12-51
reduction of nitro compounds
19-79
BIARYLS
aromatic compounds + aryl halides (hν)
14-18
aromatic compounds + aryl organometallics
11-16
aromatic compounds + aryl organometallics
14-17
aromatic compounds + arylboronates
11-16
aryl halides + alkyl or aryl organometallics
13-09
aryl halides + arylboronic acids
13-09
aryl halides + arylboronic acids
13-12
aryl halides + metals
13-11
aryl halides + trifluoroborates
13-12
aryldiazonium salts + aromatic compounds
13-27
aryldiazonium salts + metal salts
13-28
arylsulfonic acid + arylboronic acids
13-05
by benzidine rearrangement
18-36
coupling 2 aryldiazonium salts
13-28
coupling aryl halides
13-11
coupling of aromatic compounds
11-15
coupling of aryl sulfonates
13-12
Scholl Reaction
11-15
Suzuki–Miyaura coupling
13-12
Ullmann coupling
13-11
BIS(AMINES)
by benzidine rearrangement
18-36
BIS(AMIDES)
aldehydes + amides
16-18
BISULFITES
metal bisulfite + carbonyl compounds
16-12
BORANES
alkenes + borane or alkyl boranes
15-16
thermal migration of boron in boranes
18-11
BORATES (TRIFLUORO)
boranes + KHF2
12-28
BORATES
alcohols + boranes
12-28
oxidation of boranes
12-27
BORONIC ACIDS
alkyl borates + alkyl organometallics
12-28
BUNTE SALTS
from alkyl halides
10-28
CARBAMATES
alkyl halides + amines
10-17
amines + alkyl halides + CO2
12-53
amines + CO2
12-53
from aziridines
12-53
haloformates + amines
16-72
isocyanates + alcohols
16-08
CARBONATES
alcohols + phosphine
16-10
CARBOXYLIC ACIDS
acyl halides + diazo compounds
18-08
acyl peroxides + alkyl organometallics
12-26
alkylation of carboxylic acids
10-70
aromatic compounds + CO2
11-20
aromatic compounds + CO2
11-20
aromatic compounds-carboxylation
11-19
aryl nitro compounds + cyanide
13-30
Barbier–Wieland procedure
19-10
boranes + ether-acids
18-24
by decarboxylation
12-40
by Favorskii rearrangement
18-07
by malonic ester synthesis
10-67
by Michael addition
15-24
by the Cannizzaro reaction
19-81
carboxylation of alkenes
15-35
cleavage of diketones
12-43
cleavage of ketoesters
12-43
cleavage of ketones
12-45
cleavage of methyl ketones
12-44
deacyloxylation
19-59
esters + metal halides
10-51
from carboxylic acids
10-70
from lactones
10-51
from oxazolones
10-72
from RM + arenes
10-57
haloform reaction
12-44
hydrolysis of acyl halides
16-57
hydrolysis of amides
16-60
hydrolysis of anhydrides
16-58
hydrolysis of carboxylic esters
16-59
hydrolysis of diazo ketones
18-08
hydrolysis of nitriles
16-04
hydrolysis of ortho esters
10-06
hydrolysis of trihalide
10-03
ketones + peroxy acids
18-19
organometallics + CO2
16-30
oxidation of aldehydes
19-23
oxidation of aromatic rings
19-10
oxidation of aromatic side chains
19-11
oxidation of organoiron compounds
10-77
oxidation of primary alcohols
19-22
oxidative cleavage of alkenes
19-10
oxidative cleavage of alkynes
19-10
ozonolysis of alkenes
19-09
phenoxides + CO2
11-20
phosphoranes + CO2
16-44
pyrolysis of esters
17-04
rearrangement of ketones
18-19
CARBOXYLIC ACIDS, CONJUGATED
aldehydes + anhydrides
16-39
by the Knoevenagel reaction
16-38
CO2 + vinyl-M (metal)
15-22
CARBOXYLIC ESTERS
acyl halides + alcohols
16-61
acyl halides + ethers
16-61
alcohols + CO + alkenes
15-36
alcohols + CO + alkyl halides
10-77
alcohols + ketenes
15-05
alcohols + organoiron compounds
10-77
alcoholysis of acyl oxazolidinones
16-65
alcoholysis of amides
16-65
alcoholysis of nitriles
16-09
alcoholysis of trihalides
10-03
alkenes + acyl peroxides
14-09
alkenes + carboxylic acids
15-06
alkenes + carboxylic esters
15-33
alkyl halides + carboxylate anions
10-17
alkylation of oxazolidines
10-72
allylic carbonates + malonates
10-60
allylic esters + malonates
10-60
anhydrides + alcohols
16-62
aryl halides + alcohols + CO
13-15
aryl halides + alcohols + metal carbonyls
13-15
Baeyer–Villiger rearrangement
18-19
by Favorskii rearrangement
18-07
by Michael addition
15-24
by the Tishchenko reaction
19-82
carbonylation of alkyl halides and alcohols
10-77
carboxylic acids + diazo compounds
10-19
cleavage of keto-esters
12-43
condensation of aldehydes
19-82
condensation of ketones
19-84
conjugate addition of allylic silanes
15-26
esterification of carboxylic acids
16-63
esters + ethers
10-18
ethers + anhydrides
10-18
from alcohols
10-77
from alkanes
14-09
from alkyl halides
10-17
from alkyl halides
10-77
from alkyl halo sulfites
10-17
from carboxylate salts
10-17
from coupling of activated esters
10-61
from onium salts
10-17
from peroxides
14-09
from tosyl amides
10-17
hydrolysis of ortho esters
10-06
insertion of diazo esters
12-21
ketones + peroxides
18-19
oxidation of aldehydes
19-23
oxidation of methylene in ethers
19-17
oxidation of primary alcohols
19-22
oxidation of vinyl ethers
19-25
oxidative decarboxylation
19-12
oxygenation of organometallics
12-29
Pinner synthesis
16-09
rearrangement of haloketones
18-07
ring contraction of diazoketones
18-08
Sakurai reaction
15-26
transesterification
16-64
via Mitsunobu coupling
10-17
CARBOXYLIC ESTERS, CONJUGATED
Baylis–Hillman reaction
16-27
by the Knoevenagel reaction
16-38
Claisen condensation
16-36
COUMARINS
from phenols
11-11
CUMULENES
elimination of propargylic halides
17-22
CYANAMIDES
amines + cyanogen halides
10-54
CYANATES, ARYL
phenols + cyanogen halides
10-08
CYANIDES, ACYL
acyl halides + metal cyanides
16-88
CYANO IMINES
nitroso compounds + nitriles
16-42
CYANOAMINES
see amino nitriles
CYANOHYDRINS
aldehydes or ketones + HCN
16-52
aldehydes or ketones + R3SiCN
16-52
CYCLOBUTANES
by [2 + 2]-cycloaddition
15-63
extrusion of SO2
17-36
CYCLOBUTENES
ring closure of dienes
18-27
CYCLOPROPANES
alkenes + carbenes
15-64
alkenes + diazo esters
15-58
by the Simmons–Smith reaction
15-64
conjugated carbonyls + sulfur ylids
16-49
extrusion of nitrogen from pyrazolines
17-34
extrusion off CO from cyclobutanones
17-35
from pyrazoles
17-34
from pyrazolines
15-58
rearrangement of dienes
18-39
DIACETATES
oxidation of dicarboxylic acids
19-13
DIALDEHYDES
alkylation reactions
10-67
DIAMINES
aziridines + amines or ammonia
10-38
diamination of alkenes
15-53
from azido amines
10-38
reductive coupling of imines
19-76
DIAZO COMPOUNDS
acyl halides + diazomethane
16-89
base-induced elimination of N-nitroso compounds
17-33
from active methylene compounds
12-10
oxidation of hydrazones
19-06
DIAZONIUM COMPOUNDS
active methylene compounds + sulfonyl azides
12-10
aldehydes + sulfonyl azides
12-10
aromatic compounds + HONO
11-05
aryl amines + HONO
13-19
DICARBOXYLIC ACIDS
by Michael addition
15-24
from aryl isothiocyanates
11-21
oxidative cleavage of cyclic alkenes
19-10
oxidative cleavage of ketones
19-08
DIACIDS, CONJUGATED
by the Knoevenagel reaction
16-38
DIENES
addition of alkenes to dienes
15-20
addition of alkynes to alkynes
15-20
allylic halides + metals
10-56
by Stille coupling
12-15
by the Diels–Alder reaction
15-60
by the Wittig reaction
16-44
cleavage of cyclobutanes
15-63
Cope rearrangement
18-32
coupling of alkynes and allenes
15-20
coupling vinyl boranes
14-26
cycloaddition of dienes
15-66
dehydration of alkyne-alcohols
17-01
dienes + acyl metal compounds
12-16
elimination of halides
17-22
from aromatic compounds
18-27
from vinyl compounds
12-15
hydrogenation of aromatic compounds
15-13
hydrogenation of diynes
15-11
metathesis of alkenes
18-37
other cycloaddition reactions
15-66
pyrolysis of bicyclic alkene-ketones
17-28
pyrolysis of sulfoxides
17-20
rearrangement of dienes
18-32
ring closure of trienes
18-27
ring opening of cyclic alkenes
18-27
sigmatropic carbon migration
18-30
sigmatropic H migration
18-29
vinyl halides + metals
10-56
vinyl halides + RM (other metals)
10-59
vinyl-X + vinyl-M
12-15
DIESTERS
active methylene compounds + alkyl halides
10-67
alkenes + acyloxy salts
15-56
alkylation reactions
10-67
arylation
13-14
dimerization of acetals
10-64
DIHALIDES (GEMINAL)
alkenes + halogenating agents
16-23
ketones + halogenating agents
16-23
DIHALIDES
alkynes + HX
15-02
dihalogenation of alkenes
15-39
from alkyl halides + trihalides
10-57
DIIMIDES
isocyanates + phosphine oxides
16-93
DIKETONES
acyl halides + active H compounds
16-84
acylation of enamines
10-69
alkylation reactions
10-67
arylation
13-14
by Michael addition
15-24
conjugate addition of acyl halides
15-32
conjugate addition of RM with metal carbonyls
15-32
conjugated ketones + metals
10-56
coupling acyl halides
16-83
dimerization of silyl enol ethers
19-33
esters + ketones
16-86
from dithioketals
16-86
hydrolysis of furans
10-06
ketones + diazoketones
12-21
oxidation of alkynes
19-26
oxidation of methylene
19-17
oxidative cleavage of cyclic alkenes
19-10
DIKETONES, CONJUGATED
by the Knoevenagel reaction
16-38
DINITRILES
alkylation reactions
10-67
arylation
13-14
DIOLS
alkenes + formaldehyde
16-54
alkenes + halogens + metal carboxylates
15-48
by the Tollens reaction
16-43
dihydroxylation of alkenes
15-48
from halo-esters
15-48
hydride shifts of epoxides
18-41
hydrolysis of epoxides
10-07
ketones + formaldehyde
16-43
oxidation of aromatic compounds
15-49
pinacol coupling
19-76
reduction of lactones
19-38
reductive coupling of aldehydes or ketones
19-76
DISULFIDES
aryl halides + sulfides
13-04
from alkyl halides
10-27
oxidation of thiols
19-34
reduction of sulfonyl halides
19-71
DITHIOACETALS
aldehydes + thiols
16-11
from dihalides
10-26
DITHIOCARBAMATES
amines + carbon disulfide
16-22
DITHIOKETALS
alkylation of dithioketals
10-71
from dithioketals
10-13
from dithiols
10-13
ketones + CS2
16-42
ketones + thiols
16-11
vinyl sulfides + thiols
15-07
DITHIOLS
alkenes + sulfur reagents
15-51
DIYNES
by Cadiot–Chodkiewicz coupling
14-16
by Glaser coupling
14-16
by Sonogashira coupling
14-16
from alkynyl boronates
14-16
metal coupling of alkynes
13-13
metal coupling of alkynes
14-16
ENAMIDES
amines + vinyl halides
12-32
ENAMINES
alkylation of enamines
10-71
alkynes + amines
15-08
from hydroxy-amines
16-13
ENOL ETHERS: See vinyl ethers
ENOLS
and keto–enol tautomerism
12-03
EPISULFIDES: See thiiranes
EPOXIDES (Oxiranes)
aldehydes or ketones + haloorganometallics
16-24
diazonium compounds + aldehydes or ketones
16-46
epoxidation of alkenes
15-50
from halohydrins
10-09
ketones + alkenes
16-95
sulfur ylids + aldehydes or ketones
16-46
EPOXY ALCOHOLS
allylic alcohols + peroxides
15-50
from epoxy alcohols
10-14
EPOXY AMIDES
epoxidation of conjugated esters
15-50
EPOXY CARBOXYLIC ACIDS
epoxidation of conjugated acids
15-50
EPOXY ESTERS
diazo esters + aldehydes
15-64
epoxidation of conjugated esters
15-50
halo esters + aldehydes or ketones
16-40
EPOXY KETONES
epoxidation of conjugated ketones
15-50
EPOXY NITRILES
epoxidation of conjugated nitriles
15-50
ESTER AMIDES
isonitriles + carboxylic acids + aldehydes
16-98
isonitriles + carboxylic acids + ketones
16-98
ESTER SULFIDES
by the Pummerer rearrangement
19-83
rearrangement of sulfoxides
19-83
ESTERS: See Carboxylic Esters
ESTERS, INORGANIC
from alcohols
10-22
from sulfonyl halides
10-22
phosphites + alkyl halides
16-44
ESTERS, SULFONIC (see SULFONATE)
ETHER AMINES
rearrangement of halo-amines
18-18
ETHER ESTERS
conjugated esters + alcohols
15-05
ETHER KETONES
acetals + vinyl ethers
10-64
oxidation of methylene
19-15
ETHERS
acyl peroxides + alkyl organometallics
12-26
alcohols + diazo compounds
10-11
alcohols + ethers
10-13
alcohols + onium salts
10-15
alcohols + sulfonate esters
10-10
aldehydes + alcohols
16-07
alkenes + alcohols
15-05
alkenes-alkoxymercuration
15-05
alkylation of ethers
10-71
aryl halides + alkoxides
13-03
cleavage of oxonium salts
10-49
coupling of silanes
14-15
dehydration of alcohols
10-12
from alcohols (Williamson ether synthesis)
10-08
from alcohols + phenols
10-12
from alcohols
14-06
from alkyl halides (Williamson ether synthesis)
10-08
from alkyl halides
10-10
from alkyl sulfates
10-10
from carboxylic esters
10-10
from dihalides
10-10
from ethers
10-13
from haloethers
10-08
from halohydrins
10-09
from lactones and organometallics
16-30
from phenols
13-33
from trichloroimidates
10-10
ketones + alcohols
16-07
Michael addition with O nucleophiles
15-31
Organometallics + peroxides
12-26
oxidative cyclization of alcohols
14-06
phenols + diazo compounds
10-11
rearrangement of aryl sulfones
13-33
reduction of esters
19-62
reduction of lactones
19-62
reductive cleavage of acetals or ketals
19-56
Smiles rearrangement
13-33
transetherification
10-13
ETHERS, SILYL
Brook rearrangement
18-44
cleavage of ethers
10-49
from alcohols and silyl halides
10-08
rearrangement of hydroxy-silanes
18-44
FORMAMIDES
amines + trihalides
10-40
GLYCIDIC ESTERS: See epoxy esters
HALIDES, ACYL
acyl halides + HF
16-80
aldehydes + halogens
14-04
anhydrides + HF
16-80
carboxyl acids + halogenating agents
16-79
oxidation of primary alcohols
19-22
HALIDES, ALKYL
alcohols + HX
10-48
alcohols + inorganic acid halides
10-48
aldehydes + halo-boranes
16-23
alkanes + halogenating reagents
14-01
alkenes + alkyl halides
15-46
alkenes + halogenating agents
14-03
alkenes + HX
15-02
carboxylate salts + halogens
14-30
cleavage of amides
10-53
cleavage of amines
10-53
cleavage of ethers
10-49
cleavage of oxonium salts
10-49
from alcohols
10-48
from aldehydes + aromatics
10-14
from alkyl halides
10-46
from amines
10-53
from esters
10-51
from inorganic esters
10-47
from silyl ethers
10-48
from sulfonate esters
10-47
halide exchange with alkyl halides
10-46
halo-decarboxylation of acids
16-71
halogens + alkyl organometallics
12-31
halogens + boranes
12-31
halo-methylation of arenes
11-14
Hunsdiecker reaction
14-30
HALIDES, ALLYLIC
alkanes + halo-succinimides
14-03
alkenes + halogens
14-03
HALIDES, ARYL
aromatic compounds + halogen
11-10
aromatic compounds + halo-succinimides
11-10
aryl ammonium salts + halide ion
11-32
aryl halides + halogenating agent
13-07
aryldiazonium salts + metal halides
14-20
aryldiazonium salts + metal iodides
13-22
by Sandmeyer reaction
14-20
from aryl amines
14-20
from phenols
13-22
heating aryldiazonium tetrafluoroborates
13-23
phenols + phosphonium halides
13-07
rearrangement of N-haloamides
11-31
sulfonyl halides + transition metal halides
11-38
HALIDES, Silyl
From silanes
14-02
HALIDES, SULFONYL
alkanes + SO2 + halogens
14-10
aromatic compounds + sulfonyl halides
11-08
aryldiazonium salts + sulfur dioxide
14-22
sulfonic acids + halogenating agents
16-103
HALIDES, VINYL
elimination of dihalides
17-22
elimination of halides (by base)
17-13
from aldehydes or ketones
11-23
from alkynes
12-31
halide exchange with vinyl halides
10-46
halogens + vinyl boranes
12-31
halogens + vinyl-M (M = a metal)
12-31
HALOALCOHOLS (Halohydrins)
cleavage of cyclic ethers
10-49
from aldehydes or ketones
16-24
from alkenes
15-40
HALOALDEHYDES
aldehydes + halogen
12-04
aldehydes + halogenating agent
12-04
alkenes + formamides
15-47
HALOALKYNES
from alkynes
12-31
HALOAMIDES
from amides
12-53
from aziridines
10-50
HALOAMINES
alkenes + N-haloamines
15-43
from amines
12-52
HALOAZIDES
alkenes + X-N3
15-45
HALOCARBOXYLIC ACIDS
carboxylic acid + halogen
12-05
carboxylic acid + halogenating agents
12-05
from amino acids
10-52
HALOESTERS
from epoxides
10-50
HALOETHERS
from alkene-alcohols
15-51
HALOKETONES
alkenes + acyl halides
15-47
from diazoketones
10-52
from enol borinates
12-04
ketone + halogen
12-04
ketone + halogenating agents
12-04
HALOLACTAMS
halolactamization
15-41
HALOLACTONES
halolactonization
15-41
HALONITRO COMPOUNDS
alkenes + NOX
15-44
HALONITROSO COMPOUNDS
alkenes + NOX
15-44
HALOSILANES
from silanes
10-16
silanes + halogens
14-02
HALOSULFONES
sulfones + halogenation agents
12-06
HALOSULFOXIDES
sulfoxides + halogenating agents
12-06
HALOHYDRINS
alkenes + alcohols + halogens
15-40
alkenes + hypohalous acids
15-40
from epoxides
10-50
HETEROCYCLES
acylation of amines
16-77
aromatization of six-membered rings
19-01
by [3 + 2]-cycloaddition
15-58
by the heteroatom Diels–Alder reaction
15-61
by the Paterno–Büchi reaction
15-63
condensation of aldehydes
16-92
cyclization of amino-ketones or aldehydes
16-13
cyclization of haloamines
18-40
dehydrogenation reactions
19-02
dinitriles + ammonia or amines
16-21
rearrangement of acyl aziridines
18-31
thermal rearrangement of azides
18-14
furans: from diketones
16-05
indoles: Fischer indole synthesis
18-34
oxetanes: alkenes + aldehydes or ketones
16-95
oxetanes: Paterno–Büchi reaction
16-95
oxetanes: alkenes + ketones
15-63
pyrans: from diketones
16-05
pyrazoles: hydrazines + diketones
16-14
pyrazolines: alkenes + diazoalkanes
15-58
pyrazolines: hydrazines + keto-esters
16-14
pyridine derivatives: by the heteroatom Diels–Alder reaction
15-61
pyrrazolidines: alkenes + azomethine imines
15-58
pyrrolidines: cleavage of aziridines
15-58
pyrrolines: rearrangement of cyclopropyl imines
18-31
quinolines (dihydro): cyclodehydration of imines
11-13
quinolines (dihydro): from amines
11-13
quinolines (tetrahydro): cyclodehydration of amides
11-13
quinolines (tetrahydro): from amines
11-13
HYDRATES
from ketones or aldehydes
16-01
HYDRAZIDES
Imides + hydrazine
10-41
carboxylic esters + hydrazine
16-75
HYDRAZINES
reduction of azo compounds
19-51
reduction of diazo compounds
19-51
HYDRAZONES
active methylene compounds + aryldiazonium
12-07
exchange of hydrazine + hydrazones
16-14
from azo compounds
12-07
from ketones
12-07
hydrazines + aldehydes or ketones
16-14
HYDROXAMIC ACIDS
carboxylic esters + hydroxylamine
16-75
HYDROXY-ALDEHYDES
aldol condensation
16-34
dihydrooxazines + epoxides
10-72
imines + ketones
16-34
Mukaiyama aldol
16-35
oxidation of epoxides
19-20
silyl enol ethers + aldehydes
16-35
HYDROXY-AMIDES
aldehydes + amides
16-18
alkenes + amides
15-52
alkenes + sulfonyl amines
15-52
HYDROXY-AMINES: See amino alcohols
HYDROXY-AZIRIDINES
from amino epoxides
10-36
HYDROXY-CARBOXYLIC ACIDS
by the Cannizzaro reaction
19-81
rearrangement of 1,2-diketones
18-06
HYDROXY-ESTERS
Baylis–Hillman reaction
16-27
Claisen condensation
16-36
epoxides + carboxylate anions
10-14
from epoxides and RCOOH
10-18
Reformatsky reaction
16-28
transesterification of lactones
16-64
HYDROXY-ETHERS
epoxides + alcohols
10-14
HYDROXY-KETONES
acyloin condensation
19-78
aldehydes + cyanide
16-55
aldehydes and cyanide
15-32
Baylis–Hillman reaction
16-27
by aldol condensation
16-34
by rearrangement of hydroxy ketones
18-04
by the Tollens reaction
16-43
coupling of carboxylic esters
19-78
hydrolysis of diazo ketones
10-05
ketones + formaldehyde
16-43
Mukaiyama aldol
16-35
oxidation epoxides
19-20
oxidation of methylene
19-15
photolysis of epoxy ketones
10-07
rearrangement of silyloxy epoxides
18-02
reduction of epoxy ketones
19-35
silyl enol ethers + ketones
16-35
HYDROXY-NITRILES: See cyanohydrins
HYDROXY-NITRO COMPOUNDS
from epoxides
10-35
Henry reaction
16-37
HYDROXY-PHOSPHONATES
phosphonate esters + carbonyl compounds
16-44
HYDROXY-PHOSPHORAMIDES
phosphoramides + carbonyl compounds
16-44
HYDROXY-THIOCYANATES
epoxides + thiocyanate
10-14
HYDROXY-THIOETHERS
alkenes + disulfides + carboxylic acids
15-51
Claisen condensation
16-36
from epoxides
10-26
HYDROXYLAMINES
addition of organometallics to oximes
16-31
oxidation of amines
19-27
rearrangement of amine oxides
18-21
reduction of nitro compounds
19-46
IMIDES
acylation of amines
16-77
alkyl halides + imides
10-41
anhydrides + ammonia or amines
16-73
from alcohols
10-41
from aryl acyl isothiocyanates
11-21
isocyanates + phosphine oxides
16-93
IMIDINES
dinitriles + ammonia or amines
16-21
IMINES
active methylene compound + nitroso compound
12-08
addition of organometallics to nitriles
16-33
aldehydes + amines or ammonia
16-13
alkynes + amines
15-08
dehydrogenation of amines
19-05
from imines + RMgX
10-69
ketones + amines or ammonia
16-13
oxidation of primary amines
19-21
rearrangement of cyclopropyl
18-31
reductive alkylation of aldehydes or ketones
16-17
thermal rearrangement of alkyl azides
18-14
via Bischler–Napieralski reaction
10-13
IMINO ESTERS
haloimines + aroxides
18-42
ISOCYANATES
amides + hypohalites
18-13
amines + CO
12-53
base induced rearrangement of hydroxamic acids
18-15
carboxylic acids + HN3
18-16
Curtius rearrangement
18-14
from acyl halides
10-44
from alkyl halides
10-44
from nitrile oxides
18-44
Hofmann rearrangement
18-13
phosgene + amines
16-72
the Schmidt reaction
18-16
thermal rearrangement of acyl azides
18-14
ISONITRILES (ISOCYANIDES)
alkyl halides + cyanide
10-75
amines + trihalides
10-40
dehydration of formamides
17-31
from oxetanes
10-40
ISOTHIOCYANATES
from acyl halides
10-44
from alkyl halides
10-44
ISOTHIOURONIUM SALTS
from alkyl halides
10-25
KETALS
ketals + RM
10-64
ketones + alcohols
16-05
reductive cleavage of ortho esters
19-56
KETENES
base-induced elimination of acyl halides
17-14
dehydration of carboxylic acids
17-01
elimination of haloacyl halides
17-23
KETENIMINES
by the Wittig reaction
16-44
dehydration of amides
17-01
KETO-ALDEHYDES
ketals + formamides
12-16
KETO-ALKYNES
elimination of epoxy-hydrazones
17-27
KETO-AMIDES
alkenes + acyloxy salts + nitriles
15-56
amino acids + anhydrides
12-42
KETO-CARBOXYLIC ACIDS
active H compounds + CO2 or CS2
16-42
carboxylic acids + esters
16-87
KETO-ESTERS
acyl halides + active H compounds
16-84
aldehydes + diazoketones
12-18
alkenes + acyloxy salts
15-56
alkylation reactions
10-67
Claisen condensation
16-85
haloesters + esters
16-28
haloesters + nitriles
16-28
KETO-ESTERS, CONJUGATED
by the Knoevenagel reaction
16-38
KETO-NITRILES
acyl halides + active H compounds
16-84
by the Thorpe reaction
16-50
condensation of nitriles
16-50
esters + nitriles
16-86
from ketones
12-19
KETO-SULFIDES
Ketones + disulfides
12-14
KETO-SULFONES
acyl halides + active H compounds
16-84
KETO-SULFONIC ACIDS
ketones + sulfur trioxide
12-14
KETONES
acyl halides + aromatic compounds
11-17
acyl halides + organometallic compounds
16-81
addition of organometallics to nitriles
16-33
aldehydes + alkenes
15-34
aldehydes + boranes
12-18
aldehydes + heterocycles
14-19
aldehydes + transition metal complexes
12-18
alkenes + aldehydes
15-34
alkenes + alkenes + CO
15-36
alkenes + ketones
15-33
alkyl halides + organoiron compounds
10-76
alkylation of enamines
10-69
alkylation of hydrazones
10-68
alkylation of ketones
10-68
alkylation reactions
10-67
amines + HONO
12-50
and keto–enol tautomerism
12-03
aromatic compounds + acyl halides
11-17
aromatic compounds + aldehydes
14-19
aromatic compounds + anhydrides
11-17
aromatic compounds + carboxylic acids
11-17
aromatic compounds + nitriles
11-24
aryl diazonium salts + oximes
14-23
arylation of ketones
13-14
arylation
13-14
by cleavage of alkoxides
12-41
by decarboxylation
12-40
by Michael addition
15-24
carbonyl transposition
12-14
carbonylation of metal alkyls
13-15
carboxylic acids + organolithium reagents
16-29
cleavage of diketones
12-43
conjugate addition of alkyl halides
15-28
conjugate addition of allylic slanes
15-26
conjugate addition of boranes
15-27
conjugate addition of boranes
15-27
conjugate addition of organometallics
15-25
cyanoboranes + anhydrides
18-23
decarboxylative alkylation
14-31
decarboxylative coupling of 2 acids
16-90
diazo ketones + boranes
10-73
elimination (1,3) of halo-amines
17-25
elimination (1,3) of diols
17-25
elimination (1,3) of halohydrins
17-25
Friedel–Crafts acylation
11-17
Fries rearrangement
11-27
from aldehydes
12-18
from alkyl halides
10-76
from anhydrides
11-17
from aryl halides
13-15
from boranes
10-73
from cyanohydrins
10-68
from diazoketones
10-73
from dihaloalkenes
10-02
from dihydrooxazines
10-72
from dithianes
10-71
from dithioketals
10-06
from dithioketals
16-11
from enamines
10-69
from halo-ketones
10-73
from imines
10-69
from ketones
10-68
from keto-sulfoxides
10-67
from nitriles
11-24
from organometallics
12-33
haloketones + boranes
10-73
homologation of ketones
18-09
hydration of alkynes
15-04
hydration of allenes
15-04
hydrolysis of C=N compounds
16-02
hydrolysis of dithioketals
10-06
hydrolysis of dithioketals
10-71
hydrolysis of enol ethers
10-06
hydrolysis of furans
10-06
hydrolysis of gem-dihalides
10-02
hydrolysis of imines
16-33
hydrolysis of ketals
10-05
hydrolysis of nitro compounds
16-03
hydrolysis of orthoesters
10-06
hydrolysis of vinyl ethers
10-06
hydrolysis of vinyl halides
10-01
imines + RM
10-69
insertion of diazo ketones
12-21
ketenes + alkenes
15-63
keto esters + alkyl halides
10-67
ketones + diazomethane
18-09
Nef reaction
16-03
oxidation alkenes
19-25
oxidation of alcohols
19-03
oxidation of dicarboxylic acids
19-13
oxidation of methylene
19-17
oxidation of nitro compounds
19-21
oxidation of primary amines
19-21
oxidation of vinyl boranes
18-26
oxidative cleavage of alkenes
19-10
oxidative cleavage of diols
19-07
oxidative cleavage of enamines
19-10
ozonolysis of alkenes
19-09
pinacol rearrangement
18-02
pyrolysis of hydroxy-alkenes
17-32
radical addition to conjugated ketones
15-28
rearrangement of aryl esters
11-27
rearrangement of diols
18-02
rearrangement of epoxides
18-02
rearrangement of ketones
18-04
rearrangement of peroxides
18-20
ring expansion of amino alcohols
18-03
ring expansion of halohydrins
18-03
Sakurai reaction
15-26
silyl enol ethers + alkyl halides
10-68
tautomerization of enols
12-03
transesterification of vinyl esters
16-64
transition metal carbonyls + RM (M = metal)
12-33
Wacker process
19-25
Weinreb amides + organometallic compounds
16-82
KETONES, CONJUGATED
aldol condensation
16-34
alkenes + acyl halides
12-16
carbonylation of vinyl-M (M = metal)
12-33
coupling of dienones
15-20
oxidation of methylene
19-17
Pauson–Khand reaction
15-36
LACTAMS
alkyl halides from amides
10-41
and Michael addition
15-31
by Beckmann rearrangement
18-17
cyclic ketones + HN3
18-16
cyclic ketones + silyl azides
18-16
from amino carboxylic acids
16-74
from haloamides
10-41
lactams + amines
16-76
lactones + ammonia or amines
16-75
N-arylation
10-41
N-vinylation
10-41
oxidation of methylene in amines
19-17
rearrangement of oximes
18-17
reduction of imides
19-64
Schmidt reaction
18-16
LACTAMS, β
diazo-[2 + 2]-cycloaddition
15-63
enamines + ketenimines
16-96
ketenes + C=N compounds
16-96
ketones + C=N compounds
16-96
rearrangement of hydroxy-haloamines
18-18
LACTONES
alkenes + carboxylic acids
15-57
and Michael addition
15-31
Baeyer–Villiger rearrangement
18-19
condensation of dialdehydes
19-81
cyclization of allene carboxylic acids
15-06
from halocarboxylic acids
10-17
from hydroxy-carboxylic acids
16-63
oxidation of methylene in ethers
19-17
photolysis of halo-amides
18-40
rearrangement of cyclic ketones
18-19
rearrangement of lactones
18-44
reduction of anhydrides
19-63
LACTONES, β
ketones + aldehydes or ketones
16-95
NITRATES: See inorganic esters
NITRILES
aldehydes + hydroxylamines
16-16
alkenes + HCN
15-38
alkyl halides + cyanide
10-75
aromatic compounds + trihalo nitriles
11-25
aryl diazonium salts and metal cyanides
14-20
aryl halides + metal cyanides
13-08
aryl triflates + metal cyanides
11-25
by decarboxylation
12-40
by Sandmeyer reaction
14-20
carboxylic acids + cyanogen halides
16-94
cyanation α to active hydrogen compounds
12-19
cyanation α to nitrogen
12-19
cyanoborates + metal cyanide
12-34
dehydration of amides
17-30
dehydration of oximes
17-29
dehydrogenation of amines
19-05
elimination (base) of hydrazones
17-29
from iminium salts
11-25
from aldehydes
17-29
from alkyl halides
10-75
metal cyanides + alkyl organometallics
12-34
metal cyanides + aryl organometallics
13-08
Michael addition
15-24
oxidation of hydrazones
19-06
rearrangement of isonitriles
18-21
reduction of nitro compounds
19-49
NITRILES, CONJUGATED
by the Knoevenagel reaction
16-38
NITRITES: See inorganic esters
NITRO COMPOUNDS
alkanes + alkyl nitrates
12-09
alkanes + nitronium salts
12-09
alkenes + nitric acid
12-09
aryldiazonium salts + metal nitrites
14-21
by Michael addition
15-24
from alcohols
10-42
from alkyl halides
10-42
from aromatics
11-02
from aromatics
14-20
from conjugated carboxylic acids
14-13
nitration of aromatic rings
11-02
oxidation of amines
19-28
oxidation of isocyanates
19-28
oxidation of oximes
19-28
rearrangement of nitroamines
11-28
NITROALCOHOLS: See hydroxy-nitro compounds
NITRONES
from oximes
10-24
oxidation of hydroxylamines
19-06
NITROSO COMPOUNDS
Barton reaction
18-40
from active methylene compounds
12-08
nitrosation of aromatic rings
11-03
oxidation of amines
19-27
rearrangement of nitroso-amines
11-29
NITROSOAMINES
amines + HONO
12-50
ORGANOMETALLICS
alkanes + alkyl organometallics
12-22
alkanes + metals
12-23
alkenes + alkyl organometallics
15-21
alkenes + metal hydrides
15-17
alkyl halides + alkyl organometallics
12-39
alkyl halides + metals
12-38
alkynes + metal hydrides
15-17
aryl halides + metals
11-40
aryl halides + R-M (M = a metal)
11-40
formation of enolate anions
12-23
isonitriles + organolithium reagents
16-99
metal halides + RM (where M = metals)
12-36
metalation of aromatic compounds
13-17
metals + RM (where M = metals)
12-35
thioethers + organometallics
14-28
transmetalation
12-35–12-37
ORTHO ESTERS
by transetherification
10-13
carboxylic acids + alcohols
16-05
from trihalides
10-08
OSAZONES
hydrazines + hydroxy aldehydes or ketones
16-14
OXIMES
alcohols + NOCl
18-40
aldehydes or ketones + hydroxylamine
16-15
alkenes + NOX
15-44
aryldiazonium salts + oximes
14-23
Barton rearrangement
18-40
carbonyl compounds + nitrous acid
12-08
O-alkylation of oximes
10-24
reduction of nitro compounds
19-49
OXONIUM SALTS
alkyl halides + ethers
10-20
OXIRANES: See Epoxides
PEROXIDES
acid halides + alkyl hydroperoxides
10-21
acid halides + hydrogen peroxide
10-21
alkanes + oxygen
14-07
alkanes + peroxides
14-08
alkenes + oxygen
15-62
alkyl halides + hydroperoxide anion
10-21
alkyl halides + hydroperoxide anion
10-21
anhydrides + hydrogen peroxide
10-21
dienes + oxygen
15-62
from organometallics
12-29
oxidation of carboxylic acids
19-24
oxygen + alkyl organometallics
12-25
oxygen + organoboranes
12-25
photooxidation of dienes
15-62
PHENOLS
aromatic compounds + peroxides
14-05
aromatic compounds + peroxyacids
11-26
aryl halides + hydroxide
13-01
aryl sulfonic acids + hydroxide
13-02
aryldiazonium salts + water
13-20
Claisen rearrangement
18-33
Fries rearrangement
11-27
oxidation of aromatic compounds
11-26
oxidation of aryl borates
13-01
oxidation of arylboronic acids
13-01
rearrangement of allyl aryl ethers
18-33
rearrangement of aryl esters
11-27
rearrangement of aryl hydroxylamines
13-32
rearrangement of dienones
18-05
Wallach rearrangement
18-43
PHOSPHINES
alkenes + phosphines
15-08
phosphines + aryl halides
13-05
reduction of phosphine oxides
19-68
PHOSPHONATE ESTERS: See inorganic esters
PHOSPHONIUM SALTS
alkyl halides + amines
10-31
phosphines + ammonium salts
10-31
PHOSPHORANES
and the Wittig reaction
16-43
QUINONES
dyotropic rearrangement
18-44
oxidation of aromatic compounds
19-04
oxidation of aromatic compounds
19-19
oxidation of phenols
19-04
SELENIDES
aryl halides + selenide
13-04
from alkyl halides
10-26
SELENOCARBONATES
from isocyanates
16-08
SELENOETHER-ALDEHYDES
aldehyde + diselenide
12-14
SELENOETHER-KETONES
ketone + diselenide
12-14
SELENOXIDES
alkylation of selenoxides
10-71
SILANES
addition of silanes to alkenes
15-19
and dyotropic rearrangement
18-44
aryl halides + silanes
13-16
from metallated aryls
10-55
SULFIDES: See Thioethers
SULFINIC ACIDS
RM (M = a metal) + sulfonating agents
12-30
SULFONAMIDES
addition or arylboronates to C=N
16-31
dealkylation of sulfonamides
19-73
reduction of acyl sulfonamides
19-64
reduction of sulfonyl azides
19-50
sulfonyl halides + ammonia or amines
16-102
SULFONATE ESTERS
alkenes + sulfonic acids
15-06
from ethers
10-22
sulfonamides + alcohols
16-101
sulfonyl halides + alcohols
16-101
SULFONES
alkenes + sulfonyl halides
15-42
alkyl halides + sulfinic acid salts
10-29
alkyl halides + sulfonyl halides
10-29
alkylation of sulfones
10-67
alkylation of sulfones
10-71
and Michael addition
15-31
aromatic compounds + sulfonic acids
11-09
aromatic compounds + sulfonyl halides
11-09
aryl halides + sulfonate
13-04
oxidation of sulfoxides
19-31
oxidation of thioethers
19-31
sulfones + organometallics
10-61
sulfonyl halides + arylboronic acids
16-105
sulfonyl halides + organometallics
16-105
SULFONIC ACIDS
aromatic compounds + sulfuric acid
11-07
aromatic compounds + sulfuric acid
11-36
aryl halides + sulfonates
13-04
hydrolysis of sulfonyl halides
16-100
oxidation of sulfur compounds
19-30
oxidation of thiols
19-30
rearrangement of aryl sulfones
13-33
reduction of sulfonyl halides
16-104
sulfonation of aromatic compounds
11-07
sulfonation of aromatic compounds
11-36
sulfonation of methylene
19-16
SULFONIUM SALTS
alkyl halides + thioethers
10-26
SULFONYL IMINES: See halides, sulfonyl
SULFONYL IMINES
sulfonamides + aldehydes
16-18
SULFOXIDES
alkylation of sulfoxides
10-67
aromatic compounds + sulfonyl halides
11-09
oxidation of thioethers
19-31
TELLURIDES
from alkyl halides
10-26
THIIRANES (EPISULFIDES)
diazo compounds + sulfur
16-48
alkenes + sulfur reagents
15-50
from epoxides
10-26
from halo-alcohols
10-09
from halo-ketones
10-09
thioketones + sulfur ylids
16-48
THIOAMIDES
amides + sulfur reagents
16-11
amides + sulfur reagents
16-70
from nitriles
16-04
THIOCARBAMATES
from isocyanates
16-08
hydrolysis of thiocyanates
16-04
THIOCARBOXYLIC ACIDS
acyl halides + sulfur reagents
16-69
THIOCYANATES
aryl halides + thiocyanate
13-04
aryldiazonium salts + thiocyanate
13-21
from alkyl halides
10-30
from alkenes
15-42
from amines
10-30
THIOESTERS
acyl halides + thiols
16-69
esters + sulfur reagents
16-11
THIOETHER-ALDEHYDES
aldehyde + disulfides
12-14
THIOETHER-KETONES
enol ethers + disulfides
12-14
ketone + disulfides
12-14
THIOETHERS (SULFIDES)
alcohols + thiols
10-26
alkenes + thiols
15-07
alkyl halides + thiolate anions
10-26
aromatic compounds + sulfones
11-23
aryl halides + alkyl sulfides
13-04
aryldiazonium salts + sulfide
13-21
aryldiazonium salts + thiols
13-21
from alcohols
10-26
from alkyl halides
10-26
from ammonium salts
10-26
from dihalides
10-26
from organometallics
12-30
from phenols
11-23
Michael addition with S-nucleophiles
15-31
rearrangement of sulfonium salts
18-21
reduction of sulfones
19-72
reduction of sulfoxides
19-72
sulfur + alkyl organometallics
12-30
thiols + arylboronic acids
13-04
thiomethylation of aromatics
11-23
thiophenols + aromatic compounds
13-04
THIOKETONES
ketones + sulfur reagents
16-11
THIOLACTAMS
lactam + sulfur reagents
16-11
lactone + sulfur reagents
16-11
THIOLS
alkyl halides + hydrogen sulfide or HS−
10-25
aryl halides + sulfide
13-04
aryldiazonium salts + H2S
13-21
from alcohols
10-25
from Bunte salts
10-28
hydrolysis of Bunte salts
10-28
reduction of disulfides
19-75
reduction of sulfonyl halides
19-71
sulfur + alkyl organometallics
12-30
THIOUREAS
amines + CS2
16-22
isothiocyanates + amines
16-20
TRIAZOLES
alkenes + alkyl halides
15-58
TRIAZOLINES
alkenes + alkyl azides
15-58
TRIENES
aromatic compounds + carbenes
15-64
cycloaddition of dienes
15-66
ring opening of cyclic dienes
18-27
TRIHALIDES
acyl halides + halogenating agents
16-23
cleavage of methyl ketones
12-44
TRIOXANES
from aldehydes
16-92
UREAS
amines + CO2
16-22
isocyanates + amines
16-20
VINYL ETHERS (including silyl enol ethers)
alcohol + alkyne
15-05
alcohol + enol ester
10-13
alcohol + enol ether
10-13
by the Wittig reaction
16-44
cleavage of acetals or ketones
17-02
from aldehydes
12-17
from enol esters or enol ethers
10-13
from esters
16-45
from ketones
12-17
from phenols
10-08
peroxides + vinyl-M (M = a metal)
12-26
Petasis alkenylation
16-45
Tebbe alkenylation
16-45
VINYL PHOSPHINES
alkynes + phosphines
15-08
VINYL SILANES
addition of silanes to alkynes
15-19
VINYL SULFIDES
alkynes + thiols
15-07
ketones + thiols
16-11
VINYL SULFONES
alkynes + sulfonyl halides
15-42
from sulfinic acid salts
10-29
XANTHATES
carbon disulfide + alcohols
16-10