Keywords
1+2 Cycloaddition - see: Simmons-Smith; Cycloaddition Carbene; Cyclopropanation
1,1-Dipolarophile
1,3-Dipolar cycloaddition - see: Cycloaddition; Azomethine; Nitrone; Carbonyl oxide
1,3-Sigmatropic: 1,
2,
3,
4,
5
1,4-Addition - see: ConjAdd; ConjReduct; Michael
2+2 Cycloaddition - see: Cycloaddition; Ketene; Photochem
2+4 Cycloaddition - see: Diels-Alder
2+5 Cycloaddition
2,3-Sigmatropic Amine oxide
2,3-Sigmatropic Anionic: 1,
2,
3,
4
2,3-Sigmatropic Selenoxide: 1,
2
2,3-Sigmatropic Sulfoxide: 1,
2,
3,
4,
5
2,3-Sigmatropic Ylide-N
2,3-Sigmatropic Ylide-O
2,3-Sigmatropic Ylide-S
3+4 Cycloaddition - see: Oxyallyl
3,3-Sigmatropic - see: Claisen-Ireland; Claisen-Johnson; Claisen-Enol ether; etc; Cope rearrangement
Abiko-Masamune Aldol
Acetal -> Acetal
Acetal -> Acetal(thio)
Acetal -> Aldehyde: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
Acetal -> Diol: 1,
2
Acetal -> Enal: 1,
2,
3,
4,
5,
6
Acetal -> Ether
Acetal(thio) -> Acetal
Acetal(thio) -> Aldehyde: 1,
2,
3,
4
Acetal(thio) -> Enal
Acetal+Si-Alkynyl
Acetal+Si-Vinyl
Acetate pyrolysis
Acetoacetic ester synthesis: 1,
2,
3,
4
Acetonide - see: Diol -> Ketal; Ketal -> Diol
Acetylene - see: Alkyne; Ynal; Ynone; Li-Alkynyl; Mg-Alkynyl; Zn-Alkynyl; Reagents - Alkynyl-M
Acetylide - see: Li-Alkynyl; Mg-Alkynyl; etc
Acronyms: 1,
2
Acyl-Cl - see: CarboxCl
Acyl-X+Si-Vinyl
AcylImidazole+Ketoester dianion
Acyloin
Al-Alkynyl+Epoxide
Al-Alkynyl+Imine
Al-Allenyl/Propargyl+Ketone
Al-SiR3+Enal
Al-Vinyl -> Vinyl-Br
Al-Vinyl -> Vinyl-I: 1,
2
Al-Vinyl+Epoxide
Alcohol - see: Alkyl-OH; Allyl-OH; Propargyl-OH; Aryl-OH
Alcohol inversion
Alcohol inversion - see: Alkyl-OH -> Alkyl-OAc; Allyl-OH -> Allyl-OAc
Aldehyde - > Cyanoamine
Aldehyde -> α-Ketoaldehyde
Aldehyde -> Acetal: 1,
2,
3,
4
Aldehyde -> Acetal - see: Enal -> Acetal
Aldehyde -> Acetal(Me): 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
Aldehyde -> Acetal(thio): 1,
2
Aldehyde -> Aldehyde-α-OH: 1,
2,
3,
4
Aldehyde -> Alkene - see: Wittig; Corey-Fuchs;HWE; Nozaki-Takai; Peterson
Aldehyde -> Alkyl-OH: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18
Aldehyde -> Alkyne: 1,
2,
3,
4,
5,
6,
7,
8
Aldehyde -> Alkyne - see: Corey-Fuchs; Fritsch-Buttenberg-Wiechell; Reagents - Diazophosphonate; Ph
3P=CBr
2
Aldehyde -> CarboxAcid: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23
Aldehyde -> CarboxAcid - see: Pinnick oxidation; Reagents - NaClO
2
Aldehyde -> CH2: 1,
2,
3,
4,
5,
6
Aldehyde -> Cyanohydrin: 1,
2,
3,
4,
5
Aldehyde -> Enal: 1,
2,
3,
4,
5
Aldehyde -> Enamine: 1,
2,
3,
4
Aldehyde -> Enolacetate
Aldehyde -> Enolsilane
Aldehyde -> Epoxide
Aldehyde -> Imine: 1,
2,
3,
4,
5,
6,
7,
8
Aldehyde -> Oxime: 1,
2
Aldehyde azaenolate(asym)+Alkyl-X: 1,
2
Aldehyde azaenolate+Aldehyde: 1,
2,
3
Aldehyde azaenolate+Alkyl-X: 1,
2
Aldehyde azaenolate+Silyl-Cl
Aldehyde enamine+Alkyl-X
Aldehyde enamine+EneNitrile
Aldehyde Enamine+EnoateEster: 1,
2
Aldehyde enamine+Enone: 1,
2
Aldehyde enolate+Alkyl-X, Intram
Aldehyde+Aldehyde azaenolate: 1,
2,
3
Aldehyde+Alkyne
Aldehyde+B-Allenyl-Tartrate: 1,
2
Aldehyde+B-Allyl: 1,
2,
3
Aldehyde+B-Allyl-Corey
Aldehyde+B-Allyl-Ipc: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15
Aldehyde+B-Allyl-Tartrate: 1,
2,
3
Aldehyde+CarboxEster enolate: 1,
2,
3,
4
Aldehyde+CarboxEster(thio) enolate: 1,
2
Aldehyde+Ce-Vinyl: 1,
2
Aldehyde+Cr-Allyl: 1,
2
Aldehyde+Cr-Vinyl: 1,
2,
3
Aldehyde+Cu-Me
Aldehyde+Fluoride+Si-Aryl
Aldehyde+Ketene acetal: 1,
2,
3,
4,
5
Aldehyde+Ketone azaenolate
Aldehyde+Ketone enamine
Aldehyde+Ketone enolate: 1,
2,
3,
4,
5,
6,
7,
8
Aldehyde+Lactone enolate: 1,
2,
3,
4
Aldehyde+Li-Alkynyl: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
Aldehyde+Li-Allenyl/Propargyl: 1,
2
Aldehyde+Li-Allyl-P
Aldehyde+Li-Aryl: 1,
2,
3,
4
Aldehyde+Li-Benzyl
Aldehyde+Li-Cyclopropyl
Aldehyde+Li-Diazomethane
Aldehyde+Li-Epoxide: 1,
2
Aldehyde+Li-Furyl: 1,
2,
3
Aldehyde+Li-Phosphonate
Aldehyde+Li-Vinyl: 1,
2,
3,
4,
5,
6
Aldehyde+Mg-Alkyl: 1,
2,
3
Aldehyde+Mg-Alkynyl: 1,
2,
3,
4
Aldehyde+Mg-Allyl
Aldehyde+Mg-Aryl
Aldehyde+Mg-Vinyl: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
Aldehyde+Nucleophile - see: HWE; Wittig; Aldol; Corey-Fuchs
Aldehyde+Pd/Zn-Allenyl/Propargyl
Aldehyde+Si-Allenyl
Aldehyde+Si-Allyl: 1,
2,
3,
4
Aldehyde+Sn-Allenyl: 1,
2
Aldehyde+Sn-Allyl: 1,
2
Aldehyde+Sn-Vinyl
Aldehyde+Sulfonium ylide
Aldehyde+Ti-Allyl
Aldehyde+Ti/Li-Allyl-P
Aldehyde+Zn-Alkynyl
Aldehyde+Zn-Alkynyl(asym): 1,
2
Aldehyde+Zn-Allenyl/Propargyl
Aldehyde+Zn-Allyl
Alder ene reaction
Aldol - see: Ester enolate, Carboxylate enolate; etc
Aldol-B: 1,
2,
3,
4
Aldol-B-Evans: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18
Aldol-B-Ipc: 1,
2
Aldol-enamine -> Enal
Aldol-enamine -> Enone: 1,
2,
3,
4,
5,
6
Aldol-enamine -> Enone(asym)
Aldol-H+ -> Aldol
Aldol-H+ -> Enone: 1,
2,
3
Aldol-K -> Enone: 1,
2,
3,
4,
5,
6,
7,
8,
9
Aldol-Li
Aldol-Li -> Aldol: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12
Aldol-Li -> Enone: 1,
2,
3,
4
Aldol-Li -> Methylene lactone
Aldol-Na -> Aldol
Aldol-Na -> Enone: 1,
2,
3,
4,
5,
6,
7
Aldol-Na -> KetoEsterEnone: 1,
2
Aldol-Si: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13
Aldol-Zn -> Aldol
Aldol-Zn -> Enone
Alkene -> Diol-1,2: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24
Alkene -> Diol-1,2(asym): 1,
2,
3,
4
Alkene -> Enone - see: Allylic oxidation -> Enone
Alkene -> Epoxide - see: Epoxidation; Sharpless; Reagents - MCPBA; Peracid
Alkene Bromoamination
Alkene Carboalumination
Alkene Carboiodination
Alkene Carbolithiation: 1,
2
Alkene cleavage: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33
Alkene cleavage - see: Lemieux-Johnson oxidation; Ozonolysis; Reagents - KMnO
4; Pb(OAc)
4; Periodate
Alkene hydration
Alkene Hydroboration: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24
Alkene Hydrogenation: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18
Alkene Hydrostannation
Alkene hydroxylation - see: Alkene -> Diol-1,2; Reagents - OsO
4
Alkene isomerization: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13
Alkene(asym) Hydrogenation: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
Alkene+Diimide: 1,
2
Alkenyl-X - see: Vinyl-X; M-Vinyl (M = metal)
Alkyl-CN -> Alkyl-H
Alkyl-N3 -> Alkyl-NH2
Alkyl-NO2 -> Alkyl-H
Alkyl-NO2 -> Alkyl-NH2: 1,
2
Alkyl-NO2 -> Ketone
Alkyl-OAc -> Alkyl-H
Alkyl-OBn -> Alkyl-OH - see: O-Bn -> O-H; Hydrogenolysis; Reagents - DDQ
Alkyl-OH -> Aldehyde: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33,
34,
35,
36,
37,
38,
39,
40,
41,
42,
43,
44,
45,
46,
47,
48,
49,
50,
51,
52,
53,
54,
55,
56,
57,
58,
59,
60,
61,
62,
63,
64,
65,
66,
67,
68,
69,
70,
71,
72,
73,
74,
75,
76,
77,
78,
79,
80,
81,
82,
83,
84,
85,
86,
87,
88,
89,
90,
91,
92,
93,
94,
95,
96,
97,
98,
99,
100,
101
Alkyl-OH -> Aldehyde-α-NR2: 1,
2,
3
Alkyl-OH -> Aldehyde-α-OR: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13
Alkyl-OH -> Alkyl-Br: 1,
2,
3,
4,
5,
6,
7
Alkyl-OH -> Alkyl-Cl
Alkyl-OH -> Alkyl-Cl(2°): 1,
2
Alkyl-OH -> Alkyl-Cl(3°)
Alkyl-OH -> Alkyl-CN
Alkyl-OH -> Alkyl-H: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12
Alkyl-OH -> Alkyl-H - see: Barton-McCombie
Alkyl-OH -> Alkyl-H(2°): 1,
2
Alkyl-OH -> Alkyl-I: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19
Alkyl-OH -> Alkyl-I(2°)
Alkyl-OH -> Alkyl-N3: 1,
2,
3
Alkyl-OH -> Alkyl-N3(2°)
Alkyl-OH -> Alkyl-NR2: 1,
2
Alkyl-OH -> Alkyl-OBn - see: O-H -> O-Bn; O-H -> O-Me
Alkyl-OH -> Alkyl-OC(O)R: 1,
2,
3
Alkyl-OH -> Alkyl-OC(O)R(2°): 1,
2,
3
Alkyl-OH -> Alkyl-OR
Alkyl-OH -> Alkyl-OR(2°): 1,
2
Alkyl-OH -> Alkyl-SeR: 1,
2,
3,
4
Alkyl-OH -> Alkyl-SR: 1,
2,
3,
4
Alkyl-OH -> CarboxAcid: 1,
2,
3,
4,
5,
6,
7,
8,
9
Alkyl-OH -> KetoEster
Alkyl-OH -> Ketone: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33,
34,
35,
36,
37,
38,
39,
40,
41,
42,
43,
44,
45,
46,
47,
48,
49,
50,
51,
52,
53,
54,
55,
56,
57,
58,
59,
60,
61
Alkyl-OH -> Ketone-α-Br
Alkyl-OH -> Ketone-α-OR: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11
Alkyl-OH -> Ketone-1,2-di
Alkyl-OH -> Ketone-1,3-di: 1,
2
Alkyl-OMe -> Alkyl-I
Alkyl-OSO2R -> Alkyl-H: 1,
2,
3,
4
Alkyl-OSO2R -> Alkyl-OC(O)R(2°)
Alkyl-OTf+Li-Epoxide
Alkyl-S(O)R -> Alkyl-H
Alkyl-SeR -> Alkyl-H: 1,
2
Alkyl-SO2R -> Alkyl-H: 1,
2,
3,
4
Alkyl-SR -> Alkyl-H
Alkyl-X -> Alkyl-CN: 1,
2,
3,
4,
5,
6,
7,
8
Alkyl-X -> Alkyl-H: 1,
2,
3
Alkyl-X -> Alkyl-H(2°)
Alkyl-X -> Alkyl-I: 1,
2,
3,
4
Alkyl-X -> Alkyl-N3: 1,
2
Alkyl-X -> Alkyl-NH2
Alkyl-X -> Alkyl-NR2
Alkyl-X -> Alkyl-NR2 - see: N-H -> N-Alkyl
Alkyl-X -> Alkyl-ONO2
Alkyl-X -> Alkyl-Phosphonium
Alkyl-X -> Alkyl-SR: 1,
2
Alkyl-X-> Alkyl-NO2
Alkyne -> Alkynyl-I
Alkyne -> Ene-cis: 1,
2
Alkyne -> Ene-cis - see: Hydrogenation-Lindlar
Alkyne -> Ene-trans: 1,
2,
3,
4
Alkyne -> Sn-Alkynyl
Alkyne -> Vinyl-Br: 1,
2
Alkyne -> Vinyl-I: 1,
2
Alkyne Carboalumination: 1,
2,
3
Alkyne Carboauration
Alkyne Carbocupration: 1,
2,
3,
4,
5,
6
Alkyne Carbomercuration: 1,
2
Alkyne Carbometalation
Alkyne Carbonickelation: 1,
2
Alkyne Haloboration: 1,
2,
3
Alkyne hydration: 1,
2
Alkyne Hydroalumination: 1,
2,
3,
4,
5
Alkyne Hydroamination
Alkyne Hydroboration: 1,
2,
3,
4
Alkyne Hydrogenation: 1,
2,
3,
4
Alkyne Hydrostannation: 1,
2,
3,
4,
5,
6,
7,
8,
9
Alkyne Hydrosulfidation: 1,
2
Alkyne Hydrozirconation: 1,
2,
3,
4
Alkyne isomerization: 1,
2,
3
Alkyne metathesis
Alkyne Silyl-metalation: 1,
2
Alkyne+Aldehyde
Alkyne+Cu-Alkyl: 1,
2,
3,
4
Alkyne+Cu-Allyl
Alkyne+Cu-SnR3
Alkyne+Cu-Vinyl
Alkyne+Epoxide
Alkynyl-Br+Cu-Alkyl
Alkynyl-Cl -> Alkynyl-H
Alkynyl-I+Diimide
Alkynyliodonium
Alkynylmetal - see: Li-Alkynyl; Mg-Alkynyl; etc; Reagents - Alkynyl-M
Allene Hydrogenation
Allene synthesis
Allenyl-I+Cu-Vinyl: 1,
2
Allenylmetal - see: Li-Allenyl; Li-Propargyl; Si-, Sn-, Mg-, B- Ti-, Al-; Reagents - Allenyl-M
Allyl anion Cycloaddition
Allyl-B - see: B-Allyl
Allyl-H -> Allyl-X - see: Allylic oxidation
Allyl-OAc -> Allyl-N3 (Pd)
Allyl-OAc -> Allyl-OAc
Allyl-OAc+Cu-Aryl: 1,
2
Allyl-OH -> Allyl-Br: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12
Allyl-OH -> Allyl-Cl: 1,
2,
3,
4,
5,
6
Allyl-OH -> Allyl-H: 1,
2,
3
Allyl-OH -> Allyl-I
Allyl-OH -> Allyl-NR2(2°): 1,
2
Allyl-OH -> Allyl-OAc
Allyl-OH -> Allyl-OAc(2°): 1,
2,
3,
4
Allyl-OH -> Allyl-OAr(2°)
Allyl-OH -> Allyl-OSO2R
Allyl-OH -> Allyl-SR
Allyl-OH -> Diene
Allyl-OH -> Enal: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33
Allyl-OH -> EneLactone
Allyl-OH -> EnoateEster
Allyl-OH -> Enone: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33,
34,
35,
36
Allyl-OH isomerization: 1,
2,
3
Allyl-OP(O)(OR)2+Cu-Amine
Allyl-OSO2R -> Allyl-H
Allyl-OSO2R -> Allyl-OAc: 1,
2
Allyl-S(O)R -> Allyl-OH
Allyl-SR -> Allyl-H: 1,
2,
3
Allyl-X -> Allyl-H: 1,
2
Allyl-X -> Allyl-I
Allyl-X -> Allyl-OH
Allyl-X -> Allyl-OH free radical
Allyl-X -> Allyl-Phosphonium
Allyl-X -> Allyl-SO2R
Allyl-X -> Allyl-SR: 1,
2
Allyl-X -> Sn-Allyl
Allyl-X+Amine
Allyl-X+Si-Vinyl
Allyl-X+Sn-Allyl
Allylic oxidation - see: Reagents - SeO
2, O
2 (singlet}, NBS
Allylic oxidation -> Allyl-Br: 1,
2,
3,
4
Allylic oxidation -> Allyl-OH: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
Allylic oxidation -> Enal: 1,
2
Allylic oxidation -> Enone: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11
Allylsilane - see: Si-Allyl; Reagents - Allyl-Si
Allyltin - see: Sn-Allyl; Reagents - Allyl-Sn
Amide - see: CarboxAmide
Amide+In-Allyl
Aminal
Amine -> AmineOxide: 1,
2,
3
Amine -> CarboxAmide
Amine -> Formamide
Amine -> Guanidine
Amine -> Imine: 1,
2
Amine -> Isocyanate
Amine -> Isocyanide: 1,
2
Amine alkylation - see: N-H -> N-Alkyl; Amione+Alkyl-X; Reductive amination
Amine ConjAdd: 1,
2,
3
Amine epimerization
Amine oxide
Amine oxide 2,3-Sigmatropic
Amine oxide elimination
Amine+Alkyl-X: 1,
2,
3,
4,
5,
6,
7,
8
Amine+Allyl-X: 1,
2,
3
Amine+CarboxCl
Amine+Propargyl-I
Amine-3 - see: Aziridine
Amine-4
Amine-5: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33
Amine-6: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33,
34,
35,
36,
37,
38
Amine-7: 1,
2,
3
Amine-n - see: Lactam-n
Ammonium ylide
Anionic 2,3-Sigmatropic: 1,
2,
3
Anthracene -> Anthraquinone
Anthraquinone synthesis: 1,
2,
3
Ar-N=O -> Ar-NH2: 1,
2
Ar-OBn -> Ar-OH
Ar-OH -> Ar-OR
Arndt-Eistert: 1,
2
Aryl-Br -> Aryl-H
Aryl-Br -> Aryl-OMe
Aryl-H -> Aryl-Br: 1,
2
Aryl-H -> Aryl-Cl: 1,
2
Aryl-H -> Aryl-N=O
Aryl-Mg+Phosphinate
Aryl-Mg+Phosphite
Aryl-NO2 -> Aryl-NH2
Aryl-OH -> Ar-OC(O)NR2
Aryl-OH -> Ar-OSO2H
Aryl-OH -> Aryl-OMe: 1,
2,
3,
4,
5
Aryl-OH -> Aryl-OR
Aryl-OMe -> Aryl-OH: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16
Aryl-SO2R -> Ar-H
Aryllithium - see: Li-Aryl; Reagents: Aryl-Li
Asymmetric Deprotonation, amide
Aza-Claisen: 1,
2
Azaallyl anion Cycloaddition: 1,
2,
3
Azetine synthesis - see: Amine-4
Azide -> Amine: 1,
2,
3,
4,
5,
6
Azide Hydrogenation: 1,
2
Azide+Epoxide
Aziridine: 1,
2
Aziridine synthesis
Aziridine+Cyanide
Aziridine+Li-Dithiane: 1,
2
Azlactone
Azomethine ylide Cycloaddition: 1,
2,
3,
4
Azomethine ylide Retro-cycloaddition
B-Aldol: 1,
2
B-Aldol-Patterson
B-Alkyl -> Alkyl-OH
B-Alkynyl+Alkyl-X
B-Alkynyl+Me3Si-OTf
B-Allenyl-Tartrate+Aldehyde: 1,
2
B-Allyl+Aldehyde: 1,
2,
3
B-Allyl+Pyridine
B-Allyl-Corey+Aldehyde
B-Allyl-Ipc+Aldehyde: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16
B-Allyl-Tartrate+Aldehyde: 1,
2,
3,
4
B-Vinyl -> Cu-Vinyl: 1,
2
B-Vinyl -> Vinyl-H: 1,
2
Baeyer-Villiger: 1,
2,
3,
4,
5,
6,
7,
8,
9
Baeyer-Villiger -> Phenol
Baldwin rules: 1,
2
Barbier-Wieland degradation
Barton decarboxylation - see: Hunsdiecker
Barton-McCombie reduction: 1,
2,
3,
4,
5,
6,
7
Bayliss-Hillman - see: Morita-Bayliss-Hillman
Beckman rearrangement
Benzene Hydrogenation
Benzene synthesis: 1,
2,
3,
4,
5,
6
Benzyl-H -> Benzyl-OH
Benzyl-OH -> Aldehyde: 1,
2
Benzyl-OH -> Benzyl-Br
Benzyl-OH -> Benzyl-NR2
Benzyne
Benzyne Cycloaddition
Birch: 1,
2,
3
Birch alkylation: 1,
2,
3,
4,
5,
6
Birch reduction: 1,
2,
3,
4,
5,
6,
7,
8
Birch reduction - see: Reagents - Li/NH
3; Na/NH
3
Bischler-Napieralski
Bode epoxide elimination
Borane Carbonylation
Borane+Li-Alkyl
Borane+Li-Alkynyl: 1,
2
Borane+Li-Chloromethyl
Borane+Li-Dichloromethyl: 1,
2,
3,
4,
5,
6
Borane+Mg-Alkyl: 1,
2,
3
Borane+Mg-Vinyl
Borate+Mg-Allenyl/Propargyl
BoronateEster -> BoronicAcid
Bredt's Rule: 1,
2
Bromine-lithium exchange - see: Li/Br
Bromoacetate+CarboxEster enolate
Bromoacetate+Ketone enolate
Bromoamination Alkene
Bromoborane+Sn-Allyl
Bromoetherification: 1,
2,
3,
4
Bromohydrin: 1,
2
Bromolactonization
Brook elimination: 1,
2,
3
Brown Crotylation
Brown hydroboration - see: Hydroboration
C-Br -> C-H - see: Radical reduction(C-Br); Alkyl-Br -> Alkyl-H
C-CO2H -> C-Br: 1,
2
C-CO2H -> C-H - see: Decarboxylation
C-CO2H -> C-N: 1,
2,
3,
4,
5
C-I -> C-H - see: Radical reduction(C-I); Alkyl-I -> Alkyl-H
C-I -> C-Li - see: Li/I
C-OH -> C-X - see: Alkyl-OH; Allyl-OH; Benzyl-OH; etc
C-Si -> C-H - see: Si-Alkynyl -> H-Alkynyl; Si-Alkyl -> H-Alkyl; etc
C-Si -> C-OH, Alkyl: 1,
2,
3,
4,
5,
6,
7,
8
C-SO2R -> C-H - see: Alkyl-SO
2R -> Alkyl-H
C-SR -> C-H - see: Alkyl-SR -> Alkyl-H; Hydrogenolysis S-R
CaboxEster -> Carboxamide
Carbamate
Carbene
Carbene Cycloaddition: 1,
2
Carbene insertion: 1,
2,
3
Carbene, bisphenylthio
Carbenium+Si-Propargyl
Carboalumination Alkene
Carboalumination Alkyne: 1,
2,
3
Carboauration Alkyne
Carbocupration Alkyne: 1,
2,
3,
4,
5,
6
Carboiodination Alkene
Carbolithiation Alkene: 1,
2
Carbomercuration Alkyne: 1,
2
Carbometalation Alkyne
Carbonate -> Ketene acetal: 1,
2
Carbonate+CarboxEster enolate
Carbonate+Ketone enolate: 1,
2,
3,
4,
5,
6,
7
Carbonickelation Alkyne: 1,
2
Carbonium+Si-Allyl
Carbonium+Si-Vinyl
Carbonyl oxide Cycloaddition
Carbonylation
Carbonylation Borane
CarboxAcid -> Alkyl-OH: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
CarboxAcid -> CarboxAmide: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11
CarboxAcid -> CarboxAmide(Weinreb): 1,
2,
3
CarboxAcid -> CarboxCl: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18
CarboxAcid -> CarboxEster: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26
CarboxAcid -> CarboxEster(thio): 1,
2
CarboxAcid -> CarboxHydroxamate
CarboxAcid enolate+Alkyl-X: 1,
2,
3
CarboxAcid enolate+Benzyl-X
CarboxAcid enolate+Epoxide: 1,
2
CarboxAcid enolate+Ketone: 1,
2
CarboxAcid+Li-Vinyl
CarboxAmide -> Alkyl-OH: 1,
2
CarboxAmide -> Amine: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22
CarboxAmide -> CarboxAcid
CarboxAmide -> CarboxAmide-α-SePh: 1,
2,
3
CarboxAmide -> CarboxEster
CarboxAmide -> Enamine
CarboxAmide -> Imidate
CarboxAmide -> Imine: 1,
2,
3,
4
CarboxAmide -> Ketone
CarboxAmide -> Nitrile: 1,
2
CarboxAmide -> Thioamide: 1,
2,
3,
4
CarboxAmide enolate Oxidative coupling
CarboxAmide enolate(Evans) coupling
CarboxAmide enolate(Evans) Hydroxylation
CarboxAmide enolate(Evans)+Allyl-X: 1,
2,
3,
4
CarboxAmide enolate(Evans)+Propargyl-X
CarboxAmide enolate(Myers)+Alkyl-X
CarboxAmide enolate+Acyl-Imidazole
CarboxAmide enolate+Alkyl-X: 1,
2,
3
CarboxAmide enolate+CarboxCl
CarboxAmide enolate+Ketone
CarboxAmide enolate+Mander
CarboxAmide(Evans) -> Alkyl-OH: 1,
2,
3,
4,
5,
6,
7,
8,
9
CarboxAmide(Evans) -> CarboxAcid: 1,
2,
3
CarboxAmide(Evans) -> CarboxAmide(Weinreb): 1,
2,
3,
4,
5,
6
CarboxAmide(Evans) -> CarboxEster: 1,
2,
3,
4
CarboxAmide(Evans) -> CarboxEster(thio): 1,
2
CarboxAmide(Weinreb) -> Aldehyde: 1,
2,
3,
4,
5,
6,
7
CarboxAmide(Weinreb)+CarboxEster enolate
CarboxAmide(Weinreb)+Li-Alkyl
CarboxAmide(Weinreb)+Li-Alkynyl
CarboxAmide(Weinreb)+Li-Aryl
CarboxAmide(Weinreb)+Li-Vinyl: 1,
2
CarboxAmide(Weinreb)+Mg-Alkyl: 1,
2,
3,
4
CarboxAmide(Weinreb)+Mg-Vinyl
CarboxAmide+Li-Alkyl
CarboxAmide+Li-Allenyl/Propargyl
CarboxAmide+Li-Aryl
CarboxAmide+Li-Phosphonate
CarboxAmide+Li-Vinyl
CarboxAnhydride -> Alkyl-OH
CarboxAnhydride -> CarboxAcid
CarboxAnhydride+Li-Alkyl
CarboxCl -> CarboxAmide
CarboxCl -> CarboxAzide
CarboxCl+CarboxAmide enolate
CarboxCl+Cu-Me
CarboxCl+Cu-Vinyl
CarboxCl+Fe/Mg-Alkyl
CarboxCl+Ketone enolate
CarboxCl+Li-Phosphonate
CarboxCl+Mg-Alkyl
CarboxCl+Pd/Mg-Aryl
CarboxCl+Zn-Aryl
CarboxEster -> Aldehyde: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16
CarboxEster -> Alkyl-OH: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33,
34,
35,
36,
37,
38,
39,
40,
41,
42,
43,
44,
45,
46,
47,
48,
49,
50,
51,
52,
53,
54,
55,
56,
57,
58,
59,
60,
61,
62,
63
CarboxEster -> CarboxAcid: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33,
34,
35,
36,
37,
38
CarboxEster -> CarboxAmide: 1,
2,
3,
4,
5
CarboxEster -> CarboxAmide(Weinreb): 1,
2,
3
CarboxEster -> CarboxEster-α-OH: 1,
2,
3,
4
CarboxEster -> CarboxEster-α-SePh: 1,
2,
3,
4,
5,
6
CarboxEster -> CarboxHydrazide
CarboxEster -> EnoateEster: 1,
2
CarboxEster -> Ketene acetal
CarboxEster -> Ketene acetal - see: Claisen-Ireland
CarboxEster -> Ketone: 1,
2
CarboxEster enolate - see: EnoateEster enolate
CarboxEster enolate Oxidative coupling
CarboxEster enolate+
Oxaziridine
CarboxEster enolate+Aldehyde: 1,
2,
3,
4
CarboxEster enolate+Alkyl-X: 1,
2,
3,
4,
5,
6,
7,
8
CarboxEster enolate+Allyl-X: 1,
2,
3,
4,
5,
6
CarboxEster enolate+Anhydride
CarboxEster enolate+Bromoacetate
CarboxEster enolate+Carbonate
CarboxEster enolate+CarboxAmide(Weinreb)
CarboxEster enolate+CarboxEster: 1,
2,
3,
4,
5
CarboxEster enolate+Enal: 1,
2,
3
CarboxEster enolate+Enone
CarboxEster enolate+Epoxide: 1,
2
CarboxEster enolate+Formate
CarboxEster enolate+Ketone: 1,
2,
3,
4,
5
CarboxEster enolate+Lactone
CarboxEster enolate+Nitrile
CarboxEster enolate+O2
CarboxEster enolate+Vinyl-NO2
CarboxEster enolate+Ynone
CarboxEster epimerization: 1,
2,
3,
4
CarboxEster(thio) -> Aldehyde: 1,
2,
3,
4,
5
CarboxEster(thio) -> CarboxEster(thio)
CarboxEster(thio) -> Ketone
CarboxEster(thio) enolate+Aldehyde: 1,
2
CarboxEster(thio)+Cu-Alkyl
CarboxEster+CarboxEster enolate: 1,
2,
3,
4
CarboxEster+Ketone enolate
CarboxEster+Li-Alkyl
CarboxEster+Li-Allyl
CarboxEster+Li-Me: 1,
2
CarboxEster+Li-Phosphonate: 1,
2,
3
CarboxEster+Mg-Alkyl
CarboxEster+Mg-Aryl
Carboximide+Mg-Alkyl
Cationic cyclization: 1,
2,
3,
4,
5,
6,
7,
8
Ce-Alkynyl+Ketone
Ce-Furyl+Ketone
Ce-Vinyl+Aldehyde: 1,
2
Chelation control
Chelotropic, CO: 1,
2
Chelotropic, SO2: 1,
2
Chromium coupling - see: Takai-Utimoto; Nozaki-Hiyama; Reagents - CrCl
2
Claisen acylation, acyl-Cl: 1,
2,
3
Claisen acylation, Acyl-Imidazole
Claisen acylation, anhydride
Claisen acylation, carbonate: 1,
2,
3,
4,
5,
6,
7,
8
Claisen acylation, ester: 1,
2,
3
Claisen acylation, formate: 1,
2,
3,
4,
5,
6
Claisen acylation, Mander: 1,
2,
3,
4,
5,
6,
7,
8,
9
Claisen acylation, oxalate
Claisen acylation, Weinreb
Claisen(asym)
Claisen-Enol ether: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12
Claisen-Ireland: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12
Claisen-Johnson: 1,
2,
3,
4,
5,
6,
7,
8
Claisen-Johnson - Propargyl-OH
Claisen-Ketene acetal: 1,
2,
3
CompE+- Competition, Electrophile
CompE+-Enone/Vinyl-Br+Cu-R
CompE+-Acyl-X/Alkyl-X+Enolate
CompE+-Aldehyde/β-Lactone+Zn-Allyl
CompE+-Aldehyde/Aryl-I+Mg-R
CompE+-Aldehyde/Azide+Li-R
CompE+-Aldehyde/CarboxEster+Mg-R
CompE+-Aldehyde/CarboxEster+Phosphonate
CompE+-Aldehyde/CarboxEster+Wittig: 1,
2
CompE+-Aldehyde/Ketone+Allyl-Si
CompE+-Aldehyde/Ketone+Wittig: 1,
2,
3
CompE+-Aldehyde/Lactone+Wittig
CompE+-Aldehyde/Lactone-4+B-H
CompE+-Aldehyde/Vinyl-I+Li-R
CompE+-Aldehyde/Vinyl-OTf+Li-R
CompE+-Alkene/Imine+B-H
CompE+-Alkyl-Cl/Epoxide+Li-Dithiane
CompE+-Alkyl-I/CarboxEster+Li-Sulfoxide
CompE+-Alkyl-I/Neopentyl-I+Li-Alkynyl
CompE+-Alkyl-OSO2R/Alkyl(2)-Cl+NaCN
CompE+-Allyl carbonate/Azide+Cu-R
CompE+-Allyl-Br/Carbonate+Enolate
CompE+-Allyl-Br/Enoate+Li-Sulfone: 1,
2
CompE+-Allyl-OAc/Allyl-OCO2R+Pd-Enolate
CompE+-ArBr/Isocyanate+Li-R
CompE+-CarboxAmide/CarboxEster+B-H
CompE+-CarboxAmide/Ketone+B-H
CompE+-CarboxAmide/Ketone+Lawesson
CompE+-CarboxEster(thio)/Ketone+Cu-Alkyl
CompE+-CarboxEster/Aziridine+Li-R
CompE+-CarboxEster/Carbamate+Al-H
CompE+-CarboxEster/CarboxEster+Al-H
CompE+-CarboxEster/CarboxEster+KOH
CompE+-CarboxEster/Epoxide+Al-H
CompE+-CarboxEster/Urea+LiAlH4
CompE+-Carboximide/CarboxEster+Mg-R
CompE+-Ene/Ene+B-H
CompE+-Ene/Ketone+B-H
CompE+-Enoate/CarboxEster+Al-H
CompE+-EnolSi/EnolSi+Li-R
CompE+-Enone-5/Enone-6+MSR
CompE+-Enone/CarboxEster+B-H
CompE+-Enone/Enoate+B-H
CompE+-Enone/Epoxide+Li-R
CompE+-Enone/Lactone+Li-Alkynyl
CompE+-Furyl+Ketone
CompE+-H-Dithiane/H-Furyl+Li-R
CompE+-Imine/Acetal+H2O
CompE+-Ketone-Si/Epoxide+Li-Sulfone
CompE+-Ketone/CarboxAmide+Na-Alkynyl
CompE+-Ketone/CarboxEster+B-H: 1,
2
CompE+-Ketone/CarboxEster+CH2(ZnBr)2
CompE+-Ketone/CarboxEster+Li-R
CompE+-Ketone/CarboxEster+Mg-R
CompE+-Ketone/CarboxEster+Wittig
CompE+-Ketone/Enoate+B-H
CompE+-Ketone/Enoate+NaBH4
CompE+-Ketone/Enone+Amine
CompE+-Ketone/Enone+B-H: 1,
2,
3,
4,
5
CompE+-Ketone/Enone+Wittig
CompE+-Ketone/Ketone+B-H: 1,
2,
3
CompE+-Ketone/Ketone+Mg-Alkyl
CompE+-Ketone/Lactone+Ester enolate
CompE+-Ketone/Nitrile+Al-H
CompE+-Lactam/Lactone+Lawesson
CompE+-Lactone/Epoxide+NH3
CompE+-Lactone/Lactam+LiNiPr2
CompE+-Lactone/Lactone+Al-H
CompE+-Lactone/Lactone+LiNiPr2
CompE+-Lactonee/CarboxEster+Al-H
CompE+-Vinyl-I/RO-SiMe3+Li-R
CompE+-Vinyl-I/Weinreb amide+Li-R
CompElectr-BnCl/CarboxEster+Li-Dithiane
Competition - see CompElect; CompNucl; CompReduct; CompOxid
CompNu- Competition, Nucleophile
CompNu-Acetal/Enolether+H+
CompNu-Alcohol(1°)/Alcohol(1°)+SeCN
CompNu-Si-Vinyl/Alkene+Acylium
CompNu-Sn-Vinyl/B-Vinyl+Vinyl-I(Pd): 1,
2
CompOx- Competition, Oxidation
CompOx-Alcohol/Amine+CrO3: 1,
2
CompOx-Alkene/Alkene+O3: 1,
2,
3
CompOx-Alkene/Alkene+OsO4
CompOx-Alkene/Alkene+Peracid
CompOx-Alkene/Alkene+SeO2
CompOx-Alkene/Alkyne+O3: 1,
2,
3
CompOx-Alkene/Alkyne+Peracid
CompOx-Alkene/Alkyne+Peracid
CompOx-Alkene/Diene+1ΔO2
CompOx-Alkene/Enone+Dioxirane
CompOx-Alkene/Enone+OsO4
CompOx-Alkene/Enone+Peracid: 1,
2
CompOx-Alkyl-OH/Alkyl-OH+O2/Pt
CompOx-Alkyl-OH/Sulfide+CrO3: 1,
2
CompOx-Allyl-OH/Alkyl-OH+MnO2
CompOx-Lactol/Alkyl-OH+CrO3
CompOx-Lactol/Alkyl-OH+I2
CompOx-Vinyl-OAc/Alkene+OsO4
CompRed- Competition, Reduction
CompRed-Alkene/Aldehyde+H2
CompRed-Alkene/Alkene+B-H
CompRed-Alkene/Alkene+Diimide
CompRed-Alkene/Alkene+H2: 1,
2
CompRed-Alkene/Enoate+H2
CompRed-Alkene/Enone+Diimide
CompRed-Alkene/Ketone+H2
CompRed-Alkyne/Alkene+B-H
CompRed-Enone/Alkene+H2
CompRed-Vinyl-S/CarboxEster+B-H
ConjAdd = Conjugate addition (1,4-addition)
ConjAdd Amine: 1,
2,
3,
4,
5,
6,
7,
8
ConjAdd Cu-R: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19
ConjAdd Cu-SiR3
ConjAdd Enamine: 1,
2,
3,
4,
5,
6,
7,
8
ConjAdd Enolate: 1,
2,
3,
4,
5
ConjAdd Enolsilane: 1,
2
ConjAdd Ketene acetal: 1,
2
ConjAdd Ketone enolate
ConjAdd Li-R: 1,
2,
3
ConjAdd M-CN: 1,
2,
3
ConjAdd M-N3
ConjAdd M-OR: 1,
2,
3,
4,
5,
6
ConjAdd M-SR: 1,
2,
3,
4,
5,
6,
7
ConjAdd Nitronate: 1,
2
ConjAdd Si-Allyl: 1,
2
ConjAdd Sn-Allenyl
ConjAdd(asym) Cu-R: 1,
2,
3,
4
ConjAdd(asym) Li-Amide
ConjAdd(asym)-aldol Cu-R
ConjAdd-Acylation Cu-R: 1,
2
ConjAdd-Acylation Si-SeR
ConjAdd-Aldol - see: Robinson annulation
ConjAdd-Aldol Li-SiR3
ConjAdd-Alkylation Cu-Alkyl
ConjAdd-Alkylation Cu-Me
ConjAdd-Alkylation Cu-R: 1,
2,
3,
4,
5
ConjAdd-Alkylation Fulvene
ConjAdd-Alkylation Li-R
ConjAdd-Elimination Cu-R: 1,
2,
3,
4
ConjAdd-Michael Cu-R: 1,
2
ConjAdd-Silylation: 1,
2,
3
ConjReduct Enone: 1,
2,
3,
4,
5,
6,
7,
8,
9
ConjReduct-Acylation EneSulfone
ConjReduct-Acylation Enone: 1,
2
ConjReduct-Alkylation EnoateEster: 1,
2
ConjReduct-Alkylation Enone: 1,
2,
3,
4
ConjReduct-Phosphorylation
ConjReduct-Silylation Enone
ConjReduct-Triflation Enone: 1,
2,
3,
4
Conjugate addition - see: ConjAdd
Conjugate reduction - see: ConjReduct
Cope elimination: 1,
2,
3
Cope rearrangement
Corey-Chaykowsky
Corey-Fuchs: 1,
2,
3,
4,
5,
6,
7,
8
Corey-Fuchs - see: Reagents - Ph
3P=CBr
2
Corey-Kim
Cr reagents - see: Takai-Utimoto; Nozaki-Hiyama; Reagents - CrCl2
Cr-Allyl+Aldehyde: 1,
2
Cr-Arene+Li-Nitrile
Cr-Vinyl+Aldehyde: 1,
2,
3
Cram-chelation - see: Felkin-Anh
Cross metathesis - see: Olefin cross metathesis
Cu-Alkyl ConjAdd-Alkylation
Cu-Alkyl Oxidation: 1,
2
Cu-Alkyl(3°)+Enone
Cu-Alkyl+Alkyl-OSO2R
Cu-Alkyl+Alkyne: 1,
2,
3,
4
Cu-Alkyl+Alkynyl-Br
Cu-Alkyl+Allyl-OAc
Cu-Alkyl+CarboxEster(thio)
Cu-Alkyl+EnoateEster: 1,
2
Cu-Alkyl+Enone: 1,
2,
3,
4,
5,
6,
7
Cu-Alkyl+Enone-α-Si
Cu-Alkyl+Propargyl-OAc
Cu-Alkyl+Vinyl epoxide
Cu-Alkyl+Vinyl-X: 1,
2
Cu-Allyl+Alkyne
Cu-Allyl+EneLactone
Cu-Allyl+Enone
Cu-Allyl+Epoxide
Cu-Amine+Allyl-OP(O)(OR)2
Cu-Aryl+Allyl-OAc: 1,
2
Cu-Aryl+Enone: 1,
2
Cu-Me ConjAdd-Alkylation
Cu-Me+Aldehyde
Cu-Me+Allyl-OPiv
Cu-Me+CarboxCl
Cu-Me+EnoateEster: 1,
2,
3,
4,
5,
6,
7
Cu-Me+EnoateEster(thio)
Cu-Me+Enone: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14
Cu-Me+Enone-α-Si
Cu-Me+Enone-β-OR
Cu-Me+Enone-β-SR: 1,
2
Cu-Silane+EnoateEster
Cu-SiR3 + Allyl-X
Cu-SiR3+Enone
Cu-SiR3+Propargyl-OSO2R
Cu-SnR3+Alkyne
Cu-Vinyl+Alkyl-X: 1,
2,
3,
4,
5
Cu-Vinyl+Alkyne
Cu-Vinyl+Allenyl-I: 1,
2
Cu-Vinyl+Allyl-X: 1,
2
Cu-Vinyl+CarboxCl
Cu-Vinyl+CO2
Cu-Vinyl+Enal
Cu-Vinyl+EnoateAmide(Evans): 1,
2
Cu-Vinyl+Enone: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12
Cu-Vinyl+Epoxide: 1,
2,
3,
4,
5
Cu-Vinyl+Vinyl-X
Curtius: 1,
2,
3,
4,
5
CyanoAmine
CyanoAmine -> Ketone
Cyanohydrin - see: Aldehyde -> Cyanohydrin
Cyanohydrin -> AcylCyanide
Cycloaddition - see: Diels-Alder, Retro-Diels-Alder
Cycloaddition Allyl anion
Cycloaddition Azaallyl anion: 1,
2,
3
Cycloaddition Azomethine ylide: 1,
2,
3,
4
Cycloaddition Benzyne
Cycloaddition Carbene: 1,
2
Cycloaddition Carbonyl oxide
Cycloaddition Ketene: 1,
2,
3
Cycloaddition Nitrile oxide: 1,
2
Cycloaddition Nitrone: 1,
2,
3,
4
Cycloaddition Oxyallyl
Cyclobutanone synthesis
Cyclopentadienide+Alkyl-X: 1,
2
Cyclopentadienide+Ketone
Cyclopropanation - see: Simmons-Smith
Cyclopropanation Diazoester
Cyclopropanation Diazoketone: 1,
2
Cyclopropane
Cyclopropane alkylation: 1,
2
Cyclopropane Hydrogenolysis: 1,
2,
3,
4
Cyclopropane opening: 1,
2,
3,
4
Cyclopropylcarbinyl-OH -> Homoallyl-Br
Danheiser benzannulation
Decarbonylation: 1,
2,
3,
4,
5,
6,
7
Decarboxylation: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18
Decarboxylation - see: Hunsdiecker
Decarboxylation Krapcho: 1,
2,
3,
4,
5,
6,
7
Decarboxylation Oxidative: 1,
2
Decarboxylative elimination
Deconjugative alkylation: 1,
2,
3,
4,
5,
6,
7
Decyanation - see: Alkyl-CN -> Alkyl-H
Dehalogenation - see: Reductive elimination
Dehydration -> Diene: 1,
2
Dehydration -> Enal
Dehydration -> Enamine
Dehydration -> Ene: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21
Dehydration -> Ene - see: Selenoxide-E
i -> Ene
Dehydration -> EneLactone: 1,
2,
3
Dehydration -> Enoate: 1,
2,
3,
4,
5,
6
Dehydration -> Enone: 1,
2,
3
Dehydration -> Enyne
Dehydration -> Vinyl-OR
Dehydration -> Vinyl-S
Dehydration->Ene: 1,
2
Dehydroacetoxylation -> EnoateEster
Dehydroalkoxylation -> Diene
Dehydrogenation - see: Ketone -> Enone; Aldehyde -> Enal; Lactone -> EneLactone; Lactam -> EneLactam; Saegusa; Selenoxide E
i; Sulfoxide E
i; Reagents: DDQ
Dehydrohalogenation -> Alkynyl-Cl
Dehydrohalogenation -> Allyl-OR: 1,
2,
3
Dehydrohalogenation -> Ene: 1,
2,
3,
4,
5
Dehydrohalogenation -> EneLactone
Dehydrohalogenation -> Enoate
Dehydrohalogenation -> Enone: 1,
2,
3,
4,
5,
6
Dehydrohalogenation -> Vinyl-OR
Dehydrohalogenation -> Vinyl-SR
Dehydrohalogenation -> Vinyl-X
Dehydrohalogenation -> Vinyl-Xl
Dehydrosulfenylation -> EnoateEster
Dehydrosulfonoxylation -> Enamine
Dehydrosulfonoxylation -> EneLactone
Dehydrosulfonoxylation -> Enone
Dehydrosulfonoxylation -> Vinyl-NO2
Dehydrosulfonylation -> Diene: 1,
2
Dehydrosulfonylation -> EneLactone
Dehydrosulfonylation -> Enone
DeMayo cycloaddition
Deoxygenation - see: Alkyl-OH -> Alkyl-H; Wolff-Kishner; Aldehyde -> CH
2; Ketone -> CH
2; Reductive elimination
Deprotection - see: O-R -> O-H; N-R -> N-H; Ketal -> Ketone; Ketal -> Diol; Acetal -> Aldehyde
Diazoester Cyclopropanation
Diazoester ring expansion
Diazoketone: 1,
2,
3,
4,
5,
6,
7,
8
Diazoketone Cyclopropanation: 1,
2
Diazoketone, insertion
Dicarbonyl dianion - see: Ketoester dianion
Dichloromethyllithium - see: Li-Dichloromethyl
Dieckmann: 1,
2,
3,
4,
5,
6,
7
Diels-Alder, allene: 1,
2
Diels-Alder, Enal: 1,
2,
3
Diels-Alder, Enal(asym)
Diels-Alder, EneLactone
Diels-Alder, EneNitrile
Diels-Alder, EnoateAcid
Diels-Alder, EnoateEster: 1,
2,
3,
4,
5,
6
Diels-Alder, EnoateEster(asym)
Diels-Alder, Enone: 1,
2,
3,
4,
5,
6,
7,
8,
9
Diels-Alder, Intram: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27
Diels-Alder, Intram(asym)
Diels-Alder, Intram, o-Xylylene: 1,
2,
3,
4
Diels-Alder, Intram, Ynone: 1,
2
Diels-Alder, maleic anhydride: 1,
2,
3
Diels-Alder, Quinone: 1,
2,
3,
4,
5,
6,
7
Diels-Alder, sulfoxide: 1,
2
Diels-Alder, tethered
Diels-Alder, Yne: 1,
2,
3,
4,
5,
6
Diels-Alder-heterodienophile: 1,
2,
3,
4,
5,
6
Diels-Alder-inverse, Enamine: 1,
2,
3,
4
Diels-Alder-inverse, vinyl sulfide
Diene Hydrogenation: 1,
2,
3
Diene+Singlet oxygen
Dienone -> Enone
Diimide+Alkene: 1,
2
Diimide+Alkynyl-I
Diol -> Acetal: 1,
2,
3,
4,
5,
6
Diol -> Alkene
Diol -> Carbonate: 1,
2,
3
Diol -> Epoxide: 1,
2,
3,
4,
5,
6
Diol -> Ketal: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20
Diol -> Sulfite
Diol-1,2 cleavage: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19
Diol-1,2 cleavage - see: Alkene cleavage
Dioxirane - see: Reagents - DMDO
Dipolar cycloaddition - see: Cycloaddition
Dithiane - see: Li-Dithiane; Ketal(thio); Acetal(thio)
Dithiane reduction - see: Ketal(thio) -> CH
2
Domino Michael
E2 elimination - see: Dehydrobromination; Dehydroiodination; etc
Electrocyclic-4π: 1,
2,
3,
4,
5,
6,
7
Electrocyclic-6π: 1,
2,
3,
4,
5
Electrocyclic-8π: 1,
2,
3
Electrophile competition - see: CompE
+
Enal -> Acetal: 1,
2
Enal -> Acetal(Me)
Enal -> Allyl-OH: 1,
2,
3,
4,
5,
6,
7,
8
Enal -> EnoateAcid: 1,
2
Enal+Al-SiR3
Enal+CarboxEster enolate: 1,
2,
3
Enal+Cu-Vinyl
Enal+In-Allenyl/Propargyl
Enal+Ketone enolate
Enal+Li-Alkyl
Enal+Li-Alkynyl
Enal+Li-SiR3: 1,
2
Enal+Li-Vinyl
Enal+Mg-Vinyl: 1,
2
Enal+Sn-Allenyl
Enamine - see: Aldehyde enamine; Ketone enamine; ConjAdd Enamine
Enamine -> CyanoAmine
Enamine -> Enamine-β-Br
Enamine -> Imine-α-Cl
Enamine -> Ketone
Enamine ConjAdd: 1,
2,
3,
4,
5,
6,
7
Enamine(asymm)+Vinyl-NO2
Ene+Singlet oxygen
Enediolate - see: CarboxAcid enolate
EneLactam+K-OR
EneLactone Hydrogenation: 1,
2
EneLactone+Li-Selenide
EneNitrile+Aldehyde enamine
EnoateAmide(Evans)+Cu-Vinyl: 1,
2
EnoateAmide+Ketone enamine
EnoateEster -> Allyl-OH: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31
EnoateEster -> CarboxEster: 1,
2
EnoateEster ConjReduct-Alkylation: 1,
2
EnoateEster enolate+Alkyl-X
EnoateEster Epoxidation, nucleophilic: 1,
2
EnoateEster Hydrogenation: 1,
2
EnoateEster(asym) Hydrogenation
EnoateEster(thio)+Cu-Me
EnoateEster+Cu-Alkyl: 1,
2
EnoateEster+Cu-Me: 1,
2,
3,
4,
5,
6,
7
EnoateEster+Cu-Silane
EnoateEster+Enolsilane
EnoateEster+Ketoester enolate: 1,
2
EnoateEster+Ketone enolate
EnoateEster+Li-Amide
EnoateEster+Li-Selenide
EnoateEster+Nitronate
Enol -> Enolsulfide
Enolates - see: Ketone enolate; Enone enolate; Ester enolate; Aldehyde enolate; Amide enolate; Lactone enolate; EnoateEster enolate Carboxylate enolate; Pd-Enolate; Reagents - CH
2=C(OLi)
2
Enolether -> Aldehyde
Enolether -> Enal
Enolether -> Enone: 1,
2
Enolether -> Ketone: 1,
2,
3,
4,
5,
6,
7,
8
Enolether Formylation
Enolsilane - see: Mukaiyama aldol; Aldol-Si; Saegusa oxidation
Enolsilane -> Enal
Enolsilane -> Enolsilane-α-Br
Enolsilane -> Enone: 1,
2
Enolsilane -> Ketone enolate: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12
Enolsilane -> Ketone-α-Br
Enolsilane -> Ketone-α-I
Enolsilane -> Ketone-α-SePh
Enolsilane Oxidative coupling
Enolsilane+Alkyl-X: 1,
2
Enolsilane+Carbonium: 1,
2
Enolsilane+DDQ: 1,
2
Enolsilane+Dioxirane
Enolsilane+EnoateEster
Enolsilane+Imonium: 1,
2,
3
Enolsilane+MCPBA: 1,
2
Enolsilane+Orthoester
Enone -> Alkene: 1,
2,
3
Enone -> Allyl-OH: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33
Enone -> Allyl-OH(asym): 1,
2,
3,
4
Enone -> Dienone
Enone -> Enolsilane: 1,
2,
3,
4,
5,
6,
7,
8
Enone -> Enone-α-Halo: 1,
2,
3,
4,
5,
6,
7,
8,
9
Enone -> Enone-α-SeR: 1,
2,
3
Enone -> Ketal: 1,
2,
3,
4,
5,
6,
7,
8
Enone -> Ketal(Me): 1,
2,
3
Enone -> Ketal(thio): 1,
2,
3,
4
Enone -> Ketone: 1,
2,
3,
4
Enone -> Ketone - see: Hydrogenation-Enone; ConjReduct
Enone -> Vinyl-OTf: 1,
2,
3
Enone ConjAdd - see: ConjAdd
Enone ConjReduct: 1,
2,
3,
4,
5,
6,
7,
8,
9
Enone ConjReduct-Acylation: 1,
2
Enone ConjReduct-Alkylation: 1,
2,
3,
4
Enone ConjReduct-Silylation
Enone ConjReduct-Triflation: 1,
2,
3
Enone enolate dialkylation, spiro: 1,
2
Enone enolate+Alkyl-X: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11
Enone enolate+Alkyl-X(2°)
Enone enolate+Allyl-X: 1,
2,
3,
4,
5
Enone enolate+CS2
Enone enolate+Enone: 1,
2
Enone Enolate+Formaldehyde: 1,
2,
3
Enone enolate+Formate
Enone enolate+Mander: 1,
2
Enone enolate+Me-I
Enone Epoxidation, nucleophilic: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12
Enone Epoxidation, nucleophilic(asym)
Enone Hydrogenation: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
Enone+Aldehyde enamine: 1,
2
Enone+CarboxEster enolate
Enone+Cu-Alkyl: 1,
2,
3,
4,
5,
6,
7
Enone+Cu-Alkyl(3°)
Enone+Cu-Allyl
Enone+Cu-Aryl: 1,
2
Enone+Cu-Me: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14
Enone+Cu-SiR3
Enone+Cu-Vinyl: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12
Enone+Enone enolate: 1,
2
Enone+Ketoester enolate: 1,
2,
3,
4
Enone+Ketone enamine: 1,
2,
3
Enone+Ketone enolate: 1,
2,
3,
4,
5,
6
Enone+Li-Alkyl
Enone+Li-Alkynyl: 1,
2,
3
Enone+Li-Allenyl/Propargyl
Enone+Li-Allyl
Enone+Li-Allyl-S
Enone+Li-C(SPh)3
Enone+Li-Ether
Enone+Li-Furyl
Enone+Li-Me: 1,
2
Enone+Li-Nitrile
Enone+Li-Silane
Enone+Li-Vinyl: 1,
2,
3,
4
Enone+Mg-Allenyl/Propargyl
Enone+Mg-Vinyl: 1,
2,
3
Enone+Nitronate
Enone+Selenolate
Enone+Si-Allyl: 1,
2
Enone+Sn-Alkyl
Enone+Sn-Allenyl
Enone, Intram+Si-Propargyl
Enone-α-Si+Cu-Alkyl
Enone-α-Si+Cu-Me
Enone-α-Sulfonyl+Ketone Enolate
Enone-β-Amino+Ketene acetal
Enone-β-OR -> Enone: 1,
2,
3,
4,
5,
6,
7,
8,
9
Enone-β-OR+Al-H: 1,
2,
3
Enone-β-OR+Cu-Me
Enone-β-OR+Li-Alkyl: 1,
2
Enone-β-OR+Li-Aryl
Enone-β-OR+Li-Me
Enone-β-OR+Mg-Alkyl: 1,
2
Enone-β-SR+Cu-Me: 1,
2
Enone-6 -> Phenol
Enyne metathesis: 1,
2,
3,
4
Enyne reaction
Epimerization - see: Amine epimerization; Ketone epimerization; CarboxEster epimerization
Epoxidation
Epoxidation, dioxirane: 1,
2
Epoxidation, Mo
Epoxidation, nucleophilic EnoateEster: 1,
2,
3
Epoxidation, nucleophilic Enone: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12
Epoxidation, nucleophilic Vinyl-SO2R
Epoxidation, nucleophilic(asym) Enone
Epoxidation, peracid: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33,
34,
35,
36,
37
Epoxidation, Peracid - see: Reagents - MCPBA; Peracid
Epoxidation, Sharpless - see: Sharpless
Epoxidation, Ti
Epoxidation, V: 1,
2,
3,
4
Epoxidation, W
Epoxide -> Alkene
Epoxide -> Allyl-OH: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14
Epoxide -> Chlorohydrin: 1,
2
Epoxide -> Diol: 1,
2,
3,
4,
5,
6,
7,
8,
9
Epoxide elimination - see: Epoxide -> Allyl-OH; Selenoxide-E
i -> Allyl-OH
Epoxide reduction: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
Epoxide+Al-Alkynyl
Epoxide+Al-Vinyl
Epoxide+Alkyne
Epoxide+Azide
Epoxide+CarboxAcid enolate: 1,
2
Epoxide+CarboxEster enolate: 1,
2
Epoxide+Cu-Allyl
Epoxide+Cu-Vinyl: 1,
2,
3,
4,
5
Epoxide+Ketone azaenolate
Epoxide+Ketone enolate
Epoxide+Li-Alkynyl: 1,
2,
3
Epoxide+Li-Aryl
Epoxide+Li-Dithiane: 1,
2,
3,
4,
5,
6,
7,
8
Epoxide+Li-Ether
Epoxide+Li-Sulfone
Epoxide+Mg-Allyl
Epoxide+Mg-Vinyl
Epoxide+Na-Alkynyl
Epoxide+Na-Amide
Epoxide+Selenol
Epoxide+Si-Allyl
Epoxide+Thiol
Eschenmoser
Eschenmoser fragmentation
Ester - see: CarboxEster
Ester enolate+Aldehyde - see: CarboxEster enolate+Aldehyde; Aldol
Ester Pyrolysis
Ether -> Ketone
Ether-3 - see: Epoxide
Ether-4
Ether-5: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21
Ether-6: 1,
2,
3,
4,
5
Ether-7: 1,
2,
3,
4,
5
Ether-8: 1,
2,
3
Ether-9
Etherification
Evans amide - see: CarboxAmide(Evans)
Evans enolate - see: Aldol-B-Evans, CarboxAmide(Evans); EnoateAmide(Evans)
Evans-Tishchenko reduction: 1,
2
Favorski: 1,
2
Fe/Mg-Alkyl+CarboxCl
Felkin-Anh: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15
Felkin-Anh Chelation: 1,
2,
3,
4,
5,
6
Finkelstein
Finkelstein - see: Alkyl-X -> Alkyl-Y; Allyl-X -> Allyl-Y
Finkelstein reaction: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18
Fischer esterification: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
Fischer Indole: 1,
2,
3
Fleming-Tamao oxidation - see: C-Si -> C-OH
Fluorodesilylation - see: H/Si
Formaldehyde+Li/Br -> Li-Vinyl{%[Li-Vinyl
Formamide+Li-Aryl
Formate ester+Li-Vinyl
Formylation Enolether
Friedel-Crafts
Friedel-Crafts Acylation: 1,
2,
3,
4,
5
Friedel-Crafts Acylation, Ene: 1,
2,
3,
4
Friedel-Crafts Alkylation: 1,
2,
3,
4,
5
Friedel-Crafts Vinylation
Friedlander
Fries rearrangement
Fritsch-Buttenberg-Wiechell: 1,
2,
3,
4,
5,
6
Fulvene ConjAdd-Alkylation
Furan synthesis: 1,
2,
3,
4,
5
Furan+Singlet oxygen: 1,
2,
3
Furst-Plattner
Furst-Plattner (anti)
Furst-Plattner diaxial: 1,
2,
3,
4,
5,
6,
7
Gabriel synthesis
Glaser coupling
Glycol - see: Diol
Grignard reagent - see: Mg-R; Reagents - Alkyl-MgX; Allyl-MgX; Aryl-MgX; Vinyl-MgX; etc
Grob fragmentation: 1,
2,
3,
4
Grob fragmentation - oxidative
H/Si - see: Si-Alkynyl -> H-Alkynyl; Si-Alkyl -> H-Alkyl; Si-Vinyl -> H-Vinyl; etc
Haloboration Alkyne: 1,
2,
3,
4
Haloform
Halogen-metal exchange - see: Li/I; Li/Br
Heck coupling - see: Pd-Heck
Henbest: 1,
2,
3,
4,
5,
6
Henry reaction
Hg-Vinyl -> Vinyl-CO2Me
Hoffman elim
Hoffmann elim -> EneLactone
Hoffmann elim -> Enoate: 1,
2,
3,
4
Hoffmann elim -> Enone: 1,
2
Hoffmann rearrangement
Horner-Wadsworth-Emmons- see: HWE; Reagents - P(O)(OR)
2C
Hunsdiecker: 1,
2
HWE -> Diene
HWE -> DienoateEster: 1,
2,
3
HWE -> Dienone: 1,
2
HWE -> EneLactone: 1,
2
HWE -> EneSulfide: 1,
2
HWE -> EnoateAmide
HWE -> EnoateEster: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16
HWE -> EnoateEster-cis: 1,
2,
3,
4,
5,
6,
7
HWE -> Enone: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
HWE -> KetoEsterEnone
HWE -> Styrene: 1,
2
HWE -> Triene: 1,
2,
3
HWE = Horner-Wadsworth-Emmons
Hydroalumination Alkyne: 1,
2,
3,
4,
5
Hydroamination Alkyne
Hydroboration Alkene: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27
Hydroboration Alkyne: 1,
2,
3,
4
Hydroboration Vinyl-SR
Hydroformylation
Hydrogenation Alkene: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18
Hydrogenation Alkene(asym): 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
Hydrogenation Alkyne: 1,
2,
3,
4
Hydrogenation Alkyne - see: Hydrogenation Lindlar
Hydrogenation Allene
Hydrogenation Azide: 1,
2
Hydrogenation Benzene
Hydrogenation Diene: 1,
2,
3
Hydrogenation EneLactone: 1,
2
Hydrogenation EnoateEster: 1,
2
Hydrogenation EnoateEster(asym)
Hydrogenation Enone: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11
Hydrogenation Imine: 1,
2,
3
Hydrogenation Ketone
Hydrogenation Lindlar: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14
Hydrogenation Nitro
Hydrogenation Vinyl-OR
Hydrogenation Vinyl-SR
Hydrogenation/Allene
Hydrogenolysis Acyl-SR: 1,
2,
3,
4
Hydrogenolysis C-C≡N
Hydrogenolysis C-Cl
Hydrogenolysis C-OR: 1,
2
Hydrogenolysis C-S: 1,
2,
3,
4
Hydrogenolysis C-Se: 1,
2
Hydrogenolysis Cyclopropane: 1,
2,
3
Hydrogenolysis Ketone
Hydrogenolysis N-Bn - see: N-Bn -> N-H
Hydrogenolysis N-O: 1,
2,
3,
4,
5,
6,
7
Hydrogenolysis O-Bn - see: O-Bn -> O-H
Hydrohafnation, Ene -> Alkyl-OH
Hydroperoxide -> Alcohol
Hydrostannation - see: Alkyne; Alkene
Hydrostannation Alkene
Hydrostannation Alkyne: 1,
2,
3,
4,
5,
6,
7,
8,
9
Hydrosulfidation Alkyne: 1,
2
Hydroxylamine -> Nitrone: 1,
2
Hydrozirconation Alkyne: 1,
2,
3,
4
Imidate -> Amidine
Imine -> Aldehyde: 1,
2,
3
Imine -> Amine: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12
Imine -> Amine(asym)
Imine enolate - see: Aldehyde azaenolate; Ketone azaenolate
Imine Hydrogenation: 1,
2,
3
Imine+Al-Alkynyl
Imine+Li-Aryl
Imine+Mg-Vinyl
Imine+Weinreb amide enolate
Imonium
Imonium ylide - see: Azomethine ylid
Imonium+Enolsilane: 1,
2,
3
Imonium+Lactone enolate
Imonium+Li-Alkynyl
Imonium+Mg-Alkyl
Imonium+Mg-Vinyl
Imonium+Si-Allyl: 1,
2,
3
Imonium+Si-Vinyl: 1,
2,
3
Imonium+Sn-Allyl
In-Allenyl/Propargyl+Enal
In-Allyl+Amide
Indole synthesis: 1,
2,
3,
4,
5
Iodine-lithium exchange - see: Li/I
Iodoacetate+Ketoester enolate
Iodoetherification: 1,
2,
3
Iodolactonization: 1,
2,
3,
4,
5,
6,
7,
8,
9
Isocyanate+Li-Allyl
Isocyanate+Li-Aryl
Isocycanide radical
Isomerization - see: Alkene isomerization; Alkyne isomerization; Allyl-OH isomerization; Amine epimerization; Ketone epimerization; CarboxEster epimerization
Isoxazole
Jacobson kinetic resolution
Jones oxidation: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29
Julia-Kocienski: 1,
2,
3,
4,
5,
6
Julia-Lythgoe: 1,
2,
3
Julia-Type II: 1,
2
Ketal -> 1,2-Diol
Ketal -> Diol: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24
Ketal -> Enone: 1,
2,
3,
4,
5,
6,
7
Ketal -> Ketone: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33,
34
Ketal -> Vinyl-OR
Ketal(thio) -> CH2: 1,
2,
3,
4,
5,
6,
7,
8,
9
Ketal(thio) -> Enone
Ketal(thio) -> Ketal
Ketal(thio) -> Ketone: 1,
2,
3,
4,
5
Ketalization - see: Ketone -> Ketal; Aldehyde -> Acetal; Reagents - Glycol
Ketene acetal - see: Mukaiyama Aldol; Aldol-Si
Ketene acetal+β-DicarbonylEnone
Ketene acetal+Aldehyde: 1,
2,
3,
4,
5
Ketene acetal+Enone-β-Amino
Ketene Cycloaddition: 1,
2,
3,
4,
5,
6
Ketene+Alcohol
Ketene+Amine
KeteneAcetal(thio) -> CarboxAcid: 1,
2
KetoAldehyde -> Enone
Ketoamide -> Enone
Ketoester -> Enone: 1,
2,
3
KetoEster -> Ester: 1,
2
Ketoester dianion+AcylImidazole
Ketoester dianion+Alkyl-X: 1,
2
Ketoester dianion+Allyl-X: 1,
2,
3,
4
Ketoester enolate+Alkyl-X
Ketoester enolate+EnoateEster: 1,
2
Ketoester enolate+Enone: 1,
2,
3,
4
Ketoester enolate+Iodoacetate
Ketone -> Alkene: 1,
2,
3
Ketone -> Alkene - see: Wittig; Corey-Fuchs; HWE; Nozaki-Takai; Peterson; Ketone -> C=CH
2
Ketone -> Alkyl-OH: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33,
34,
35,
36,
37,
38,
39,
40,
41,
42,
43,
44,
45,
46,
47,
48,
49,
50,
51,
52,
53,
54,
55,
56
Ketone -> Alkyl-OH(asym): 1,
2,
3,
4,
5,
6
Ketone -> Amine - see: Reductive amination
Ketone -> C=CH2: 1,
2,
3,
4,
5,
6
Ketone -> C=CH2 - see: Wittig-methyl; Nozaki-Takai; Takai-Utimoto
Ketone -> CH2: 1,
2,
3,
4,
5,
6,
7,
8,
9
Ketone -> Enamine: 1,
2,
3,
4
Ketone -> Enolborane: 1,
2
Ketone -> Enolether: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
Ketone -> Enolphosphate: 1,
2
Ketone -> Enolsilane: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28
Ketone -> Enone: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29
Ketone -> Enone - see: Selenoxide; Sulfoxide; Saegusa; Dehydrohalogenation
Ketone -> Hydrazone: 1,
2
Ketone -> Imine: 1,
2,
3
Ketone -> Ketal: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30
Ketone -> Ketal - see: Enone -> Ketal
Ketone -> Ketal(Me): 1,
2,
3,
4,
5
Ketone -> Ketal(thio): 1,
2
Ketone -> Ketone-α-Br: 1,
2,
3,
4,
5,
6,
7,
8
Ketone -> Ketone-α-Cl
Ketone -> Ketone-α-OH: 1,
2,
3,
4,
5,
6,
7,
8,
9
Ketone -> Ketone-α-OR: 1,
2
Ketone -> Ketone-α-SePh: 1,
2
Ketone -> Ketone-α-SeR: 1,
2,
3,
4,
5,
6,
7,
8,
9
Ketone -> Ketone-α-SR
Ketone -> Ketone-1,2-di: 1,
2
Ketone -> Oxime
Ketone -> Vinyl-OP(O)(OR)2: 1,
2,
3,
4
Ketone -> Vinyl-OTf: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13
Ketone azaenolate+Aldehyde
Ketone azaenolate+Allyl-Br
Ketone azaenolate+CarboxEster
Ketone azaenolate+Epoxide
Ketone enamine+Aldehyde
Ketone enamine+Alkyl-X: 1,
2
Ketone enamine+Alkyl-X, Intram
Ketone enamine+Allyl-X
Ketone enamine+EnoateAmide
Ketone enamine+Enone: 1,
2,
3
Ketone enamine+Ketone
Ketone enamine+Thionium
Ketone enolate - see: Enone enolate; Enolsilane
Ketone enolate dimerization
Ketone enolate+Aldehyde: 1,
2,
3,
4,
5,
6,
7,
8
Ketone enolate+Aldehyde - see: Aldol
Ketone enolate+Alkyl-X: 1,
2,
3,
4,
5,
6,
7
Ketone enolate+Alkyl-X, Intram: 1,
2,
3,
4
Ketone enolate+Allyl-X: 1,
2,
3,
4,
5
Ketone enolate+Allyl-X, Intram: 1,
2
Ketone enolate+Bromoacetate: 1,
2,
3,
4,
5
Ketone enolate+Carbonate: 1,
2,
3,
4,
5,
6,
7
Ketone enolate+CarboxCl
Ketone enolate+CarboxEster: 1,
2,
3
Ketone enolate+Chlorocarbonate
Ketone enolate+CO2: 1,
2
Ketone enolate+CS2: 1,
2
Ketone enolate+Enal
Ketone enolate+EneNitrile
Ketone enolate+EnoateEster
Ketone enolate+Enone: 1,
2,
3,
4,
5,
6
Ketone Enolate+Enone-α-Sulfonyl
Ketone enolate+Epoxide
Ketone enolate+Formate: 1,
2,
3
Ketone enolate+Ketone
Ketone enolate+Mander: 1,
2,
3,
4,
5,
6,
7
Ketone enolate+Me-I: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12
Ketone enolate+NCS
Ketone enolate+O2
Ketone enolate+Oxaziridine
Ketone enolate+Oxetane
Ketone enolate+Propargyl-X
Ketone enolate+Vinyl-NO2: 1,
2
Ketone enolate+Vinyl-Phosphonium
Ketone epimerization: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13
Ketone Hydrogenation
Ketone olefination
Ketone olefination - see: Wittig, HWE;
Ketone protection - see: Ketone -> Ketal; Ketal -> Ketone; Ketone -> Enolether
Ketone protection enolate
Ketone reduction: see: Ketone -> CH
2; Ketal(thio) -> CH2; Reagents - LiAlH
4; NaBH
4; Bu
2AlH; etc
Ketone+Al-Allenyl/Propargyl
Ketone+CarboxAcid enolate: 1,
2
Ketone+CarboxAmide enolate
Ketone+CarboxEster enolate: 1,
2,
3,
4,
5
Ketone+Ce-Alkynyl
Ketone+Ce-Furyl
Ketone+CompE+-Furyl
Ketone+Cyclopentadienide
Ketone+Ketone enamine
Ketone+Ketone enolate
Ketone+Li-Alkyl
Ketone+Li-Alkynyl: 1,
2
Ketone+Li-Allenyl/Propargyl
Ketone+Li-Aryl
Ketone+Li-Dibromomethyl: 1,
2,
3
Ketone+Li-Dichloromethyl
Ketone+Li-Dithiane
Ketone+Li-Ether: 1,
2
Ketone+Li-Me: 1,
2,
3,
4,
5,
6,
7,
8,
9
Ketone+Li-Phosphine
Ketone+Li-Silane
Ketone+Li-Sulfone: 1,
2,
3
Ketone+Li-Vinyl: 1,
2,
3
Ketone+Mg-Alkyl: 1,
2,
3,
4,
5,
6,
7
Ketone+Mg-Alkynyl
Ketone+Mg-Vinyl: 1,
2,
3,
4,
5
Ketone+Na-Alkynyl
Ketone+Si-Allenyl
Ketone+Si-Allyl: 1,
2
Ketone+Sulfonium ylide
Ketone+Ti-Allenyl/Propargyl
Ketone+Wittig-alkyl: 1,
2
Ketone-α-Br -> Enone
Ketone-α-OH cleavage
Ketone-α-OR -> Ketone: 1,
2
Ketone-α-S(O)nR -> Ketone: 1,
2,
3,
4
Ketone-β-OH -> Ketone-1,3-di
Ketone-1,2-di: 1,
2,
3
Ketone-1,3-di enolate+Alkyl-X: 1,
2
Ketophosphonate dianion+Alkyl-X: 1,
2
KetoSulfone enolate + Alkyl-X
Ketosulfoxide dianion
Kinetic resolution - Ketone reduction
Knoevenagel condensation: 1,
2,
3
Knorr
Kolbe
Kornblum oxidation: 1,
2
Kowalski reaction: 1,
2
Krapcho Decarboxylation: 1,
2,
3,
4,
5,
6,
7,
8
Kumada coupling: 1,
2,
3
Kumada coupling - see: Pd/Mg
Lactam -> EneLactam: 1,
2,
3,
4
Lactam enolate+Alkyl-OTf(asym)
Lactam enolate+Allyl-X
Lactam enolate+CO2
Lactam-15+: 1,
2
Lactam-5: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15
Lactam-6: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16
Lactol -> Ether
Lactol -> Lactone: 1,
2,
3,
4,
5,
6
Lactone -> Alkyl-OH
Lactone -> EneLactone: 1,
2,
3,
4
Lactone -> Ester
Lactone -> Lactol: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12
Lactone -> Lactone-α-HO
Lactone -> Lactone-α-OH: 1,
2
Lactone -> Orthoester
Lactone enolate+Aldehyde: 1,
2,
3,
4
Lactone enolate+Alkyl-X: 1,
2,
3,
4,
5,
6,
7,
8
Lactone enolate+Allyl-X: 1,
2
Lactone enolate+Formaldehyde: 1,
2,
3
Lactone enolate+Imonium
Lactone+Li-Me
Lactone-10: 1,
2
Lactone-11
Lactone-13
Lactone-14: 1,
2,
3
Lactone-15+: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12
Lactone-4: 1,
2,
3,
4,
5
Lactone-5: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33,
34,
35,
36,
37,
38,
39,
40,
41,
42,
43,
44,
45,
46,
47,
48,
49,
50,
51,
52,
53,
54,
55
Lactone-6: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23
Lactone-8: 1,
2
Lactonization - see: Yamaguchi; Seleno-; Iodo-; Macrolactonization
Lemieux-Johnson oxidation: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12
Ley oxidation
Ley oxidation - see: Reagents - TPAP
Li-Alkyl -> B-Alkyl
Li-Alkyl -> Zn-Alkyl: 1,
2
Li-Alkyl+CarboxAmide
Li-Alkyl+CarboxAnhydride
Li-Alkyl+CarboxEster
Li-Alkyl+Enal
Li-Alkyl+Enone: 1,
2,
3
Li-Alkyl+Ketone
Li-Alkyl+Styrene
Li-Alkynyl -> B-Alkynyl: 1,
2
Li-Alkynyl -> Sn-Alkynyl
Li-Alkynyl -> Zn-Alkynyl
Li-Alkynyl+Aldehyde: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
Li-Alkynyl+Alkyl-X: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
Li-Alkynyl+CarboxAmide(Weinreb)
Li-Alkynyl+Chlorocarbonate: 1,
2
Li-Alkynyl+Enal
Li-Alkynyl+Enone: 1,
2,
3
Li-Alkynyl+Epoxide: 1,
2,
3
Li-Alkynyl+Formaldehyde: 1,
2,
3
Li-Alkynyl+Imonium
Li-Alkynyl+Ketone: 1,
2
Li-Alkynyl+Me-X: 1,
2,
3,
4
Li-Alkynyl+Pyridinium
Li-Allenyl/Propargyl+Aldehyde: 1,
2
Li-Allenyl/Propargyl+Alkyl-X
Li-Allenyl/Propargyl+Allyl-Cl
Li-Allenyl/Propargyl+CarboxAmide
Li-Allenyl/Propargyl+Enone
Li-Allenyl/Propargyl+Ketone
Li-Allenyl/Propargyl-Se+Alkyl-X
Li-Allyl -> B-Allyl
Li-Allyl -> Sn-Allyl
Li-Allyl+CarboxEster
Li-Allyl+Enone
Li-Allyl+Isocyanate
Li-Allyl-P+Aldehyde
Li-Allyl-S+Allyl-Cl
Li-Allyl-S+Enone
Li-Allyl-Si+Alkyl-X
Li-Amide+EnoateEster
Li-Amine+Alkyl-X
Li-Aryl -> Aryl-I: 1,
2
Li-Aryl -> Ce-Aryl
Li-Aryl -> Sn-Aryl
Li-Aryl+
Formamide
Li-Aryl+Aldehyde: 1,
2,
3,
4
Li-Aryl+CarboxAmide
Li-Aryl+CarboxAmide(Weinreb)
Li-Aryl+CO2
Li-Aryl+Enone-β-OR
Li-Aryl+Epoxide
Li-Aryl+Formamide
Li-Aryl+Imine
Li-Aryl+Isocyanate
Li-Aryl+Ketone
Li-Aryl+Me-I: 1,
2
Li-Aryl+Oxalate
Li-Aryl+Vinyl-SO2R
Li-Benzyl+Aldehyde
Li-Benzyl+O2
Li-C(SPh)3+Enone
Li-Chloromethyl+Borane
Li-Cyclopentadienide+Alkyl-X
Li-Cyclopropyl -> Mg-Cyclopropyl
Li-Cyclopropyl+Aldehyde
Li-Diazomethane+Aldehyde
Li-Dibromomethyl+Ketone: 1,
2,
3
Li-Dichloromethyl+Borane: 1,
2,
3,
4,
5,
6
Li-Dichloromethyl+Ketone
Li-Dithiane+Alkyl-X: 1,
2,
3,
4,
5,
6,
7,
8
Li-Dithiane+Aziridine: 1,
2
Li-Dithiane+Epoxide: 1,
2,
3,
4,
5,
6,
7,
8
Li-Dithiane+Ketone
Li-Epoxide+Aldehyde: 1,
2
Li-Epoxide+Alkyl-OTf
Li-Ether -> Zn-Ether
Li-Ether+Enone
Li-Ether+Epoxide
Li-Ether+Ketone: 1,
2
Li-Furyl+Aldehyde: 1,
2,
3
Li-Furyl+Alkyl-X
Li-Furyl+Enone
Li-Isocyanide
Li-Ketoesterdiyl - see: Dicarbonyl dianion
Li-Me+CarboxEster: 1,
2
Li-Me+Enone: 1,
2,
3
Li-Me+Ketone: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
Li-Me+Lactone
Li-Nitrile+Alkyl-X: 1,
2,
3,
4,
5,
6,
7,
8
Li-Nitrile+Cr-Arene
Li-Nitrile+Enone
Li-Nitrile+Epoxide
Li-Phosphine Oxidative coupling
Li-Phosphine+Ketone
Li-Phosphonate+Aldehyde
Li-Phosphonate+Aldehyde - see: HWE
Li-Phosphonate+CarboxAmide
Li-Phosphonate+CarboxCl
Li-Phosphonate+CarboxEster: 1,
2,
3
Li-Phosphonate+Lactone
Li-Pyridyl+Me-I
Li-Selenide+EneLactone
Li-Selenide+EnoateEster
Li-Silane+Enone
Li-Silane+Ketone
Li-SiR3+Enal: 1,
2
Li-Sulfide+Allyl-Br
Li-Sulfide+Borane: 1,
2
Li-Sulfide+Vinyl-NO2
Li-Sulfone+Alkyl-X: 1,
2,
3,
4,
5,
6
Li-Sulfone+Alkyl-X, Intram
Li-Sulfone+Allyl-X: 1,
2
Li-Sulfone+Epoxide
Li-Sulfone+Ketone: 1,
2,
3
Li-Sulfoxide+Alkyl-X
Li-Sulfoxide+Thioester
Li-Vinyl - see: Li/I; Li/Sn; Li/Br; Li/H; Reagents - Vinyl-Li
Li-Vinyl -> Cu-Vinyl - see: Cu-Vinyl
Li-Vinyl -> Mg-Vinyl: 1,
2,
3,
4
Li-Vinyl -> Sn-Vinyl
Li-Vinyl -> Zn-Vinyl: 1,
2,
3,
4,
5,
6
Li-Vinyl+Aldehyde: 1,
2,
3,
4,
5,
6
Li-Vinyl+Alkyl-X: 1,
2
Li-Vinyl+Allyl-X: 1,
2
Li-Vinyl+CarboxAcid
Li-Vinyl+CarboxAmide
Li-Vinyl+CarboxAmide(Weinreb): 1,
2
Li-Vinyl+Enal
Li-Vinyl+Enone: 1,
2,
3,
4,
5
Li-Vinyl+Formaldehyde
Li-Vinyl+Formate ester
Li-Vinyl+Ketone: 1,
2,
3
Li-Vinyl+Oxetane
Li/Br -> Li-Alkyl
Li/Br -> Li-Aryl: 1,
2,
3
Li/Br -> Li-Cyclopropyl
Li/Br -> Li-Furyl: 1,
2
Li/Br -> Li-Vinyl: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13
Li/Br -> Li-Vinyl{%[Li-Vinyl+Formaldehyde
Li/H -> Li-Alkynyl: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33,
34,
35,
36,
37,
38,
39,
40
Li/H -> Li-Allyl: 1,
2
Li/H -> Li-Allyl-X: 1,
2,
3,
4
Li/H -> Li-Amine: 1,
2,
3
Li/H -> Li-Aryl: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
Li/H -> Li-Aryloxazoline
Li/H -> Li-Benzyl
Li/H -> Li-Dithiane: 1,
2,
3,
4,
5
Li/H -> Li-Epoxide
Li/H -> Li-Furyl
Li/H -> Li-Indole: 1,
2,
3,
4
Li/H -> Li-Pyridyl: 1,
2,
3
Li/H -> Li-Pyrone
Li/H -> Li-Quinoline
Li/H -> Li-Vinyl-OR: 1,
2,
3,
4
Li/H(asym) -> Li-Allyl -> Ti-Allyl
Li/H(asym) -> Li-Ether
Li/I -> Li-Alkyl: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14
Li/I -> Li-Aryl
Li/I -> Li-Pyridyl
Li/I -> Li-Vinyl: 1,
2,
3,
4,
5,
6,
7,
8
Li/S -> Li-Alkyl: 1,
2
Li/Sn -> Li-Amine
Li/Sn -> Li-Azaallyl: 1,
2
Li/Sn -> Li-Cyclopropyl: 1,
2
Li/Sn -> Li-Dithiane
Li/Sn -> Li-Ether: 1,
2,
3,
4
Li/Sn -> Li-Vinyl: 1,
2,
3,
4,
5,
6
Lindlar - see: Hydrogenation Lindlar
Lithiation - see: Li/H, Li/I; Li/Br; Li/Sn; etc
Lithiothioacetal - see: Li-Dithiane; Li-Sulfide
Luche reduction: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12
Luche reduction - see: Reagents - BH
4- Na
+, CeCl3
Macrolactamization
Macrolactonization: 1,
2,
3,
4,
5,
6
Malonic Ester Synthesis
Mander reagent - see: Reagents - O=C(OR)CN
Mander+CarboxAmide enolate
Mander+Enone enolate: 1,
2
Mander+Ketone enolate: 1,
2,
3,
4,
5,
6,
7
Mannich: 1,
2,
3,
4,
5,
6,
7,
8,
9
Mannich carboiodination
Mannich, vinylogous: 1,
2,
3
McMurry coupling: 1,
2,
3
McMurry coupling -> Diol
Mechanism: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33,
34,
35,
36,
37,
38,
39,
40,
41,
42,
43,
44,
45,
46,
47,
48,
49,
50,
51,
52,
53,
54,
55,
56,
57,
58,
59,
60,
61,
62,
63,
64,
65,
66,
67,
68,
69,
70,
71,
72,
73
Meerwein-Ponndorf-Verley: 1,
2
Meisenheimer rearrangement
Metal-halogen exchange - see: Li/I; Li/Br
Metalate rearrangement (B): 1,
2,
3,
4,
5,
6,
7,
8
Metalate rearrangement (Cu)
Metalation - see: Li/H
Metaloenamine - see: Aldehyde azaenolate; Ketone azaenolate
Metathesis - see: RCM; Enyne metathesis; Olefin cross metathesis; Reagents - Grubbs
Methylenation - see: Wittig; Nozaki-Takai; Reagents - CH
2Br
2, Zn; CH
2I
2, Zn; PPh
3=CR
2
Meyer-Schuster Rearrangement
Mg-Alkyl+Aldehyde: 1,
2,
3
Mg-Alkyl+Borane: 1,
2,
3
Mg-Alkyl+CarboxAmide(Weinreb): 1,
2,
3
Mg-Alkyl+CarboxCl
Mg-Alkyl+CarboxEster
Mg-Alkyl+Carboximide
Mg-Alkyl+CO2
Mg-Alkyl+Enone-β-OR: 1,
2
Mg-Alkyl+Formate
Mg-Alkyl+Imonium
Mg-Alkyl+Ketone: 1,
2,
3,
4,
5,
6,
7,
8,
9
Mg-Alkyl+Nitrile: 1,
2
Mg-Alkyl+Ynal
Mg-Alkyl+Ynone
Mg-Alkynyl+Aldehyde: 1,
2,
3,
4
Mg-Alkynyl+Ketone: 1,
2
Mg-Allenyl/Propargyl+Borate
Mg-Allenyl/Propargyl+Enone
Mg-Allyl+Aldehyde
Mg-Allyl+Epoxide
Mg-Aryl+Aldehyde
Mg-Aryl+Aryl-OMe
Mg-Aryl+CarboxEster
Mg-Me -> Ce-Me
Mg-Vinyl -> Ce-Vinyl: 1,
2
Mg-Vinyl+Aldehyde: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
Mg-Vinyl+Borane
Mg-Vinyl+CarboxAmide(Weinreb)
Mg-Vinyl+Enal: 1,
2
Mg-Vinyl+Enone: 1,
2,
3
Mg-Vinyl+Epoxide
Mg-Vinyl+Imine
Mg-Vinyl+Imonium
Mg-Vinyl+Ketone: 1,
2,
3,
4,
5
Michael Acrolein
Michael Acrylonitrile
Michael addition - see: ConjAdd; ConjReduct; Robinson annulation
Michael Enone: 1,
2
Michael(asym) Enone-6
Mislow-Evans rearrangement - see: 2,3-Sigmatropic
Mitsunobu -> Acetal
Mitsunobu -> Amine: 1,
2,
3,
4
Mitsunobu -> Azide: 1,
2,
3
Mitsunobu -> Aziridine
Mitsunobu -> Br: 1,
2
Mitsunobu -> Cl: 1,
2
Mitsunobu -> Ester: 1,
2,
3,
4,
5,
6,
7,
8,
9
Mitsunobu -> Ether: 1,
2,
3,
4
Mitsunobu -> Hydrazine
Mitsunobu -> Lactone-15+
Mitsunobu -> SeR
Mitsunobu -> SR: 1,
2,
3,
4
Morita-Bayliss-Hillman: 1,
2
Morita-Bayliss-Hillman(asym)
Mukaiyama Aldol: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
N-Allyl -> N-H: 1,
2,
3
N-Bn -> N-H: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
N-Boc -> N-H: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20
N-C(O)CF3 -> N-H
N-C(O)OR -> N-Me
N-C(O)R -> N-H: 1,
2,
3,
4
N-Cbz -> N-H: 1,
2,
3,
4,
5
N-CHO -> N-H
N-CHO -> NC
N-CO2R -> N-H: 1,
2,
3,
4,
5,
6
N-CO2R -> N-Me: 1,
2
N-H -> N-Ac - see: N-H -> N-C(O)R
N-H -> N-Alkyl: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27
N-H -> N-Alkyl - see: Alkyl-X -> Alkyl-NR
2; N-H -> N-Me
N-H -> N-Alkyl(2°): 1,
2,
3
N-H -> N-Allyl
N-H -> N-Bn
N-H -> N-Boc: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
N-H -> N-C(O)CF3
N-H -> N-C(O)H
N-H -> N-C(O)NR2
N-H -> N-C(O)OR: 1,
2,
3,
4,
5,
6,
7
N-H -> N-C(O)R: 1,
2,
3,
4,
5,
6,
7
N-H -> N-Cbz: 1,
2
N-H -> N-Me: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10
N-H -> N-MOM
N-H -> N-PMB: 1,
2,
3
N-H -> N-Propargyl
N-H -> N-SEM
N-H -> N-SiMe2tBu
N-H -> N-SO2R: 1,
2,
3,
4,
5
N-H -> N-Troc
N-H -> N-Vinyl
N-Me -> N-C(O)OR: 1,
2
N-MOM -> N-H
N-OH -> N=O
N-OR -> N-H: 1,
2,
3,
4,
5,
6
N-Phthal -> N-H
N-PMB -> N-H: 1,
2
N-R -> N-OH
N-S(O)R -> N-H: 1,
2
N-SEM -> N-H: 1,
2
N-SiiPr3 -> N-H
N-SiMe2tBu -> N-H
N-SO2R -> N-H: 1,
2,
3,
4,
5,
6,
7,
8,
9
N-Troc -> N-H
Na-Alkynyl+Epoxide
Na-Alkynyl+Ketone
Na/H -> Na-Alkynyl: 1,
2
Naphthalene synthesis
Naphthoquinone synthesis
Nazarov: 1,
2,
3,
4,
5,
6
Nef reaction: 1,
2
Negishi coupling: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13
Negishi coupling - see: Pd/Zn
NH2 -> N=C=O
Ni-Aldehyde Hydrocarbation
Ni-Carbometalation, Ene
Ni/B-Aryl+Alkyl-Br(2°)
Nitrile -> Aldehyde: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14
Nitrile -> Amine: 1,
2,
3,
4
Nitrile -> CarboxAcid: 1,
2,
3,
4,
5
Nitrile -> CarboxEster: 1,
2,
3
Nitrile -> Imine: 1,
2
Nitrile -> Nitrile-α-SePh
Nitrile anion - see: Li-Nitrile
Nitrile anion+CarboxEster
Nitrile oxide Cycloaddition: 1,
2
Nitrile+CarboxEster enolate
Nitrile+Mg-Alkyl -> Ketone: 1,
2
Nitro -> Aldehyde
Nitro -> Amine
Nitro -> Nitrile oxide
Nitro aldol
Nitro compounds - see: Vinyl-NO
2, Alkyl-NO
2, Aryl-NO
2, etc
Nitro Hydrogenation
Nitronate+EnoateEster
Nitronate+Enone
Nitrone -> Hydroxylamine
Nitrone -> Oxaziridine
Nitrone Cycloaddition: 1,
2,
3,
4,
5,
6,
7
Nitrone Retro-Cycloaddition: 1,
2
Nitrone synthesis: 1,
2
Nitroso ene
Nozaki-Hiyama coupling: 1,
2,
3,
4,
5
Nozaki-Takai -> Ene: 1,
2,
3,
4,
5
Nucleophile competition, see CompNu
O-tBu -> O-H: 1,
2
O-Allyl -> -O-H
O-Bn -> O-H: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31
O-C(O)H -> O-H
O-C(O)NR2 -> O-H
O-C(O)OR -> O-H
O-C(O)R -> O-H: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18
O-Ethoxyethyl -> O-H: 1,
2,
3,
4
O-H -> Aldehyde - see: Alkyl-OH -> Aldehyde
O-H -> O-Alkyl: 1,
2,
3,
4
O-H -> O-Allyl
O-H -> O-Bn: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11
O-H -> O-Boc
O-H -> O-C(O)NR2
O-H -> O-C(O)NR2: 1,
2
O-H -> O-C(O)OR: 1,
2,
3
O-H -> O-C(O)R: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33,
34,
35,
36,
37,
38,
39,
40,
41,
42,
43,
44,
45,
46
O-H -> O-C(S)NR2: 1,
2
O-H -> O-C(S)OR: 1,
2,
3
O-H -> O-C(S)SR
O-H -> O-CPh3
O-H -> O-Ethoxyethyl: 1,
2,
3
O-H -> O-Me: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15
O-H -> O-MEM: 1,
2,
3
O-H -> O-Methoxypropyl
O-H -> O-MOM: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16
O-H -> O-P(O)(NR2)2
O-H -> O-P(O)(OR)2
O-H -> O-Piv
O-H -> O-PMB: 1,
2,
3,
4
O-H -> O-PNBz
O-H -> O-SEM: 1,
2,
3,
4
O-H -> O-SiiPr3: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14
O-H -> O-SiEt3: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22
O-H -> O-SiMe2tBu: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33,
34,
35,
36,
37,
38,
39,
40,
41,
42,
43,
44,
45,
46,
47,
48,
49,
50,
51,
52,
53,
54,
55,
56,
57,
58,
59,
60,
61,
62,
63,
64,
65,
66,
67,
68,
69,
70,
71,
72,
73,
74,
75,
76,
77,
78,
79
O-H -> O-SiMe2CH2Br
O-H -> O-SiMe3: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11
O-H -> O-SiPh2tBu: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17
O-H -> O-SO2R: 1,
2,
3,
4,
5,
6,
7,
8,
9,
10,
11,
12,
13,
14,
15,
16,
17,
18,
19,
20,
21,
22,
23,
24,
25,
26,
27,
28,
29,
30,
31,
32,
33,
34,
35,
36,
37,
38,
39,
40,
41,
42,
43,
44,
45,
46,
47
O-H -> O-Tf: 1,
2,
3,