Named Reactions A-D

Akabori Amino Acid Reactions
NH2
OH R
sugar
~
OEt R
Na/Hg HCI/EtOH
H R
o
s. Akabori,
J. Chern. Soc. Japan 52, 606 (1931); Ber. 66, 143, 151 (1933); J Chern. Soc. 64,608 (1943).
Copyright © 2005 Nathan T. Reynolds
Aldol Reaction (Condensation)

o
OH
R. Kane, Ann. Phys. Chern., Sere 2,44,475

(1838);
Algar- Flynn -Oyamada Reaction

Ar Ar
OH
o
J. Algar, J. P. Flynn, Prac. Roy. Irish Acad. 42B, 1 (1934); B. Oyamada, J Chern. Soc. Japan 55, 1256 (1934).
Allan-Robinson Reaction
o o
Ar
o o
o
J. Allan, R. Robinson, J Chern. Soc. 125,2192 (1924).

Arens-van Dorp Synthesis; Isler Modification

Me
CI
1) LiNH2
OH
OEt
2) acetophenone
D. A. van Dorp, J. F. Arens, Nature 160,189 (1947); J. F. Arens et ale Rec. Trav. Chim. 68, 604, 609 (1949);0. Isler et al., He lv. Chim. Acta 39,259 (1956).
Arndt-Eistert Synthesis
o
R
OH
o
R
CI
o
OH
F. Arndt, B. Eistert, Ber. 68,200 (1935).

Auwers Synthesis
Br Ar
-OH EtOH
OH
o
K. v. Auwers et al., Ber. 41,4233 (1908); 48,85 (1915); 49,809 (1916); K. v. Auwers, P. Pohl, Ann. 405,243 (1914).
Baeyer-Drewson Indigo Synthesis

o o
dil. NaOH
HN
A. Baeyer,
v. Drewson, Ber.
15,2856 (1882).
Baeyer- Villiger Reaction

o o
A. Baeyer,
v. Villiger,
Ber. 32, 3625 (1899); 33, 858 (1900).
Baker- Venkataraman Rearrangement

o
Base.
o
Ph
w. Baker, J
Chern. Soc. 1933, 1381; H. S. Mahal, K. Venkataraman, ibid. 1934, 1767.

Bam.berger Rearrangem.ent
HO
E. Bamberger, Ber. 27, 1347, 1548 (1894).

Bam.ford-Stevens Reaction
/N,
R R H
Ts
Na
R2 = H, alkyl
w. R. Bamford,
T. S. Stevens, J Chern. Soc. 1952, 4735.

Barbier( -type) Reaction

o
OH
M = Mg, Li, Sm(II), Zn
x = Br, CI, I
P. Barbier, C. R. A cad. Sci. 128,110 (1899).

Barbier-Wieland Degradation
OMe
1) 2PhMgX 2) HX
o
OH
H. Wieland, Ber. 45,484 (1912); P. Barbier, R. Locquin, Compt. Rend. 156,1443 (1913).
Bart Reaction
o
~S/O-Na+ b-Na+
Sheller Modification:
H. Bart, DE 250264 (1910); DE 254092 (1910); DE 264924 (1910); DE 268172 (1912); Ann. 429,55 (1922); E. Scheller, GB 261026; A. w. Ruddy et al., J Am. Chern. Soc. 64, 828 (1942).
Barton Decarboxylation
OH
o
R OH
I N
1) DCC, DMAP 2) BU3SnH
D. H. R. Barton et al., Chern. Commun. 1983, 939

Barton Olefin Synthesis

o
3) Pb(OAc)4 4) PR3, ~
1)
)::::::N=N
D. H. R. Barton et al., Chern. Commun. 1970, 1226

Barton-McCotnbie Reaction
R'
s
D. H. R. Barton, S. W. McCombie, Perkin Trans. I 1975, 1574.
Barton-Zard Reaction
o
R NC:
Base
•
R
R1
D. H. R. Barton et al., Tetrahedron 46,7587 (1990).
Baudisch Reaction
H2NOH H202 Cu2+
,.
0, 0 ,
I I
Cu
I , I I ,
' , II
00
o. Baudisch et aI., Naturwiss. 27, 768, 769 (1939); Science 92,336

(1940); J Am. Chern. Soc. 63, 622 (1941).
Baylis-Hillman Reaction
o
~EWG OH EWG R
A. B. Baylis, M. E. D. Hillman, DE 2155113; eidem, US 3743669 (1972, 1973). Copyright © 2005 Nathan T. Reynolds
Beckmann Rearrangelllent
o
PCI5
NH
E. Beckmann, Ber. 19, 988 (1886).

Benkeser Reduction
Li or Ca
R. A. Benkeser et al., J Am. Chern. Soc. 74, 5699 (1952); 77, 3230 (1955).
Benzidine Rearrangement
A. W. Hofmann, Proc. Roy. Soc. London 12, 576 (1863); P. Jacobson et al., Ber. 26,688 (1893).
Benzilic Acid Rearrangement

o
OH
KOH.
Ar Ar
Ar
Ar OH
J. Liebig, Ann. 25, 27 (1838); N. Zinin, ibid. 31, 329 (1939).

Benzoin Condensation
o
2
Ar H OH
KeN.
Ar
Ar
A. J. Lapworth, J Chern. Soc. 83,995 (1903); 85,1206 (1904).

Bergman Reaction
~
.
•
R. R. Jones, R. G. Bergman, J Am. Chern. Soc. 94,660 (1972); R. G. Bergman, Accts. Chern. Res. 6,25 (1973).
Bergmann Azlactone Peptide Synthesis eOOH

I CHNH2 I CH I
COOH
1) Solvent 2) H2 3) Hel
HN Bn
CH2COOH
M. Bergmann et al., Ann. 449,277 (1926).

Bergmann Degradation
o
1) BnOH
N3
2) M, H2;
H20
o
M. Bergmann, Science 79, 439 (1934).
Bernthsen Acridine Synthesis

H N
RC02H
N~
R
A. Bemthsen, Ann. 192,1 (1878); 224,1 (1884).
Betti Reaction
OH N~ N~ OH NHR
M. Betti, Gazz. Chim. Ital. 30 II, 301 (1900); 33 II, 2 (1903);

Bechamp Reduction
Fe
Hel
A. J. Bechamp, Ann. Chim. Phys. 42(3), 186, (1854).

Benary Reaction
o
E. Benary, Ber. 63, 1573 (1930); 64,2543 (1931).
Biginelli Reaction
o
Me
o o
H
H N
NH Me
P. Biginelli, Ber. 24, 1317,2962 (1891); 26,447 (1893).

Birch Reduction
R R
Na, liq. NH3 Alcohol R= EDG R=EWG
A. J. Birch, J. Chern. Soc. 1944, 430; 1945, 809; 1946, 593; 1947, 102,1642,1949,2531.
Bischler-Mohlau Indole o Synthesis

Br
A. Bischler et al., Ber. 25,2860 (1892); 26, 1336 (1893); R. Mohlau, ibid. 14, 171 (1881); 15,2480(1882)
Bischler- N apieralski Reaction

HN
R
A. Bischler, B. Napieralski, Ber. 26, 1903 (1893).
Blaise Ketone Synthesis

o
0
CI RZnCI
E. E. Blaise, A. Koehler, Bull. Soc. Chim. [4] 7,215 (1910)

Blaise Reaction
o
Br OR
Zn, R'CN KOH (aq)
o
R'
o
OR
E. E. Blaise, Compt. Rend. 132, 478 (1901).

Blanc Reaction
CI
G. Blanc, Bull. Soc. Chim. France [4],33,313 (1923).

Blanc Reaction-Blanc Rule

o
HO
0
OH
n = 2,3 A is product n >3 B is product
H. G. Blanc, Compt. Rend. 144, 1356 (1907).

Bodroux Reaction
o
2 R"NHMgX
o
OR'
NHR"
F. Bodroux, Bull. Soc. Chim. France 33, 831 (1905), 35, 519 (1906);
Bodroux-Chichibabin Aldehyde Synthesis

HC(OEt)3
RMgX;
o
R H
F. Bodroux, Compt. Rend. 138,92 (1904); A. E. Chichibabin, Ber. 37, 186,850 (1904).
Bogert-Cook Synthesis
o
1)
MgBr
Ph
M. T. Bogert, Science 77, 289 (1933); J. W. Cook, C. L. Hewett, J Chern. Soc. 1933, 1098.
Bohn-Schmidt Reaction
o
Hg
OH
OH OH
OH
OH
R. Bohn, DE 46654 (1889); R. E. Schmidt, DE 60855 (1891).
Boord Olefin Synthesis

0
R 1) EtOH,
2) Br2
Hel
3)R1MgX 4) Zn(dust)
R1
L. C. Swallen, C. E. Boord, J Am. Chern. Soc. 52, 651 (1930); 53,1505 (1931); 55, 3293 (1933);
Borsche-Drechsel Cyclization
~
1) Hel
E. Drechsel, J Prakt. Chern. 38(2), 69 (1858); W. Borsche, M. Feise, Ber. 20,378 (1904).
Bouveault Aldehyde Synthesis

o
L. Bouveault, Bull. Soc. Chim. France 31, 1306, 1322 (1904).

Bouveault-Blanc Reduction
o
Na
OH MeOH
R
L. Bouveault, G. Blanc, Compt. Rend. 136, 1676 (1903)

Boyland-Sims Oxidation
NR2
1) KOH (aq.),
OH
E. Boyland et al., J. Chern. Soc. 1953, 3623; E. Boyland, P. Sims, ibid. 1954, 980.
Bradsher Cyclization
AcOH
c. K. Bradsher, T. W. G. Solomons, J
(1958).
Am. Chern. Soc. 80,933
Bradsher Reaction
HBr AcOH
c. K. Bradsher,
J Am. Chern. Soc. 62,486 (1940).

Brook Rearrangement
Base
n
1,2,3
A. G. Brook,J. Am. Chern. Soc. 80,1886 (1958)

Bucherer Carbazole Synthesis

~
NaHS03
OH
H. T. Bucherer, F. Seyde, J. Prakt. Chern. 77(2),403 (1908).

Bucherer Reaction
OH
H. T. Bucherer, J Prakt. Chern. [2] 69,49 (1904)

Bucherer-Bergs Reaction
o
R
N
KeN
H R
HN
H. T. Bucherer, H. T. Fischbeck, J Prakt. Chern. 140, 69 (1934); H. T. Bucherer, W. Steiner, ibid. 291; H. Bergs, DE 566094 (1929).
Buchner-Curtius-Schlotterbeck Reaction
o
R H
o
R
E. Buchner, T. Curtius, Ber. 18,2371 (1885); F. Schlotterbeck, Ber. 40,479 (1907); 42, 2559 (1909).
Buchwald-Hartwig Cross Coupling Reaction

x
RNH2
PdCl2(dppf) NaOtBu/THF.
~
NHR
J. Louie, J. F. Hartwig, Tetrahedron Letters 36,3609 (1995); A. Guram et al., Angew. Chern. Int. Ed. 34, 1348 (1995).
s.
Cadiot-Chodkiewicz coupling
CuCI
R--==CH
R'---==CBr
R'----==~---=~-R
w. Chodkiewicz et al., Compt. Rend. 245,322 (1957);

Camps Quinoline Synthesis

OH
Me
NaOH ROH
Me
OH
R. Camps, Ber. 22,3228 (1899); Arch. Pharm. 237, 659 (1899); 239, 591 (1901).
Cannizzaro Reaction
s. Cannizzaro, Ann.
(1854).
88, 129 (1853); K. List, H. Limpricht, Ann. 90, 180
Carroll Rearrangement
RIO R OH
0 0
Base
0
Me
•
R R
Me
CO2
M. F. Carroll, J Chern. Soc. 1940,704; 1941,507

Castro-Stephens Coupling
x
R R Cu
Pd/pyridine
C. E. Castro, R. D. Stephens, J. Org. Chern. 28,2163 (1963)

Chapm.an Rearrangem.ent
o
o. MUlTIlTI et al.,Ber. 48, 379 (1915);

Chern. Soc. 127,1992(1925);
A. W. Chapman, J. 1927,174; 1929,569.
Chichibabin Pyridine Synthesis

H R R R
,# N
A. E. Chichibabin, J Russ. Phys. Chern. Soc. 37, 1229 (1906)

Chichibabin Reaction
#
N
1216 (1914),
A. E. Chichibabin,
o. A. Zeide, J. Russ.
Phys. Chern. Soc. 46,
Chugaev Reaction
OH
1) CS2 2) NaOH, CH31 3) L1
L. Chugaev (Tschugaeff), Ber. 32, 3332 (1899).

Ciamician- Dennstedt Rearrangement

CI
G. L. Ciamician, M. Dennstedt, Ber. 14, 1153 (1881).

Claisen Condensation
o
2
Base
•
Me
o
OR'
L. Claisen, O. Lowman, Ber. 20, 651 (1887).

Claisen Rearrangement
R R
L. Claisen, Ber. 45,3157 (1912); L. Claisen, E. Tietze, ibid. 58,275 (1925); 59,2344 (1926).
Claisen-Schmidt Condensation
o
H R
o
NaOH
L. Claisen, A. Claparede, Ber. 14,2460 (1881); J. G. Schmidt, ibid. 1459.

Clernmensen Reduction
o
R
Zn(Hg)
Hel
E. Clemmensen, Ber. 46, 1837 (1913); 47, 51, 681 (1914).

Com.bes Quinoline Synthesis

R
0 0
aniline;
R1
H2SO4
•
N
R1
A. Combes, Bull. Soc. Chim. France 49,89 (1888).

Conia Reaction
o
F. Rouessac et al., Tetrahedron Letters 1965, 3319. Review: J. M. Conia, P. Le Perchec, Synthesis 1975, 1-19.
Conrad-Limpach Cyclization
OH
o
R
aniline
M. Conrad, L. Limpach, Ber. 20, 944 (1887); 24,2990 (1891).

Cope Elimination Reaction

80
H
\®/Me N--Me
fl.
A. C. Cope et al., J Am. Chern. Soc. 71,3929 (1949);

Cope Rearrangement
R R
..
A. C. Cope et al., J. Am. Chern. Soc. 62, 441 (1940).
Corey-Bakshi-Shibata Reduction
Ph Ph
0
N-. / B
\ 1
BH3, THF
••
..',OH ••
RS
RL
E. J. Corey et al., J. Am. Chern. Soc. 109,5551 (1987).

Corey-Fuchs Reactions
o
R
H
2) BuLi
¢Jfo
R
Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972,3769.

Corey-Kim Oxidation
o
N-S
(f)/
Me
Cia
Me
OH
o
then base
E. J. Corey, C. U. Kim, J Am. Chern. Soc. 94,7586 (1972).

Corey-Winter Olefin Synthesis

OH • · · • · · • R · · · • • · OH
•
R' R' R
E. J. Corey, R. A. E. Winter, J Am. Chern. Soc. 85,2677 (1963).

Cornforth Rearrangefilent
u::::c
R
J. w. Cornforth, The Chemistry of Penicillin (Princeton University Press, New Jersey, 1949) p 700.
Craig Method
HX
..
L. C. Craig, J. Am. Chern. Soc. 56, 231 (1934).

Criegee Reaction
o
PbOAc4
R. Criegee, Ber. 64, 260 (1931).

Curtius Rearrangement
o
R N3
T. Curtius, Ber. 23,3023 (1890)
Dakin Reaction
OH OH
NaOH
H
OH
H. D. Dal<in, Am. Chern. J 42,477 (1909).
Dakin-West Reaction
o
HN R Me Me
o
(1928).
H. D. Dakin, R. West, J Bioi. Chern. 78,91,745,757

Darzens Condensation
o
R
o
OEt
1) EtO2) HO-
o
• R
3) ~
G. Darzens, Compt. Rend. 139,1214 (1904); 141,766 (1905); 142, 214 (1906).
Darzens Synthesis of Tetra lin Derivatives
l\i1e G. Darzens, Compt. Rend. 183,748 (1926).

Darzens-Nenitzescu Synthesis of Ketones o

o
R R
AICI3 RCDCI AICI3 cyclohexane
R
CI G. Darzens, Comp t. Rend. 150,707 (1910); C. D. Nenitzescu, I. P. Cantuniari, Ann. 510,269 (1934);
Co ri ht © 2005 Nathan T. Re nolds
Delepine Reaction
N
2) HX
M. Delepine, Compt. Rend. 120,501 (1895); 124,292 (1897).

Demjanov Rearrangement
OH
OH
OH N. J. Demjanov, M. Lushnikov, J Russ. Phys. Chern. Soc. 35, 26 (1903)

Dess-Martin Oxidation
OH
D. B. Dess, J. C. Martin, J Org. Chern. 48, 4155 (1983).

Dieckmann Reaction
o
Base.
w. Dieckmann, Ber. 27, 102,965 (1894); 33,595,

2670, (1900); Ann. 317, 51, 93, (1901).
Diels-Alder Reaction
R
R
K. Alder, Ann. 460, 98 (1928); 470, 62 (1929); Ber. 62,2081,2087 (1929).

o. Diels,
Dienone- Phenol Rearrangement

o
OH
K. von Auwers, K. Ziegler, Ann. 425,217 (1921).

Dimroth Rearrangement
Me
NH
o. Dimroth, Ann.
364, 183 (1909); 459, 39 (1927).
Doebner Reaction
o
OH
OH
o
H
N (1894).
o. Doebner, Ann. 242,265 (1887); Ber. 20,277 (1887); 27, 352,2020
Doebner-Miller Reaction
R R
o
o. Doebner, w. v. Miller, Ber.
16,2464 (1883).
Doering- Laf'lammc Allene Synthesis

1) t-BuOK, CHBr3 2) Na or Mg
w. von E. Doering, P. M. LaFlalTIlTIe, Tetrahedron 2,75

(1958); US 2933544 (1960).

Named Reactions A-D

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Named Reactions A-D

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Akabori Amino Acid Reactions

Aldol Reaction (Condensation)

R. Kane, Ann. Phys. Chern., Sere 2,44,475

Algar- Flynn -Oyamada Reaction

J. Allan, R. Robinson, J Chern. Soc. 125,2192 (1924).

Arens-van Dorp Synthesis; Isler Modification

F. Arndt, B. Eistert, Ber. 68,200 (1935).

Baeyer-Drewson Indigo Synthesis

Copyright © 2005 Nathan T. Reynolds

Baeyer- Villiger Reaction

Ber. 32, 3625 (1899); 33, 858 (1900).

Copyright © 2005 Nathan T. Reynolds

Baker- Venkataraman Rearrangement

Chern. Soc. 1933, 1381; H. S. Mahal, K. Venkataraman, ibid. 1934, 1767.

E. Bamberger, Ber. 27, 1347, 1548 (1894).

T. S. Stevens, J Chern. Soc. 1952, 4735.

Barbier( -type) Reaction

M = Mg, Li, Sm(II), Zn

P. Barbier, C. R. A cad. Sci. 128,110 (1899).

1) DCC, DMAP 2) BU3SnH

D. H. R. Barton et al., Chern. Commun. 1983, 939

Barton Olefin Synthesis

D. H. R. Barton et al., Chern. Commun. 1970, 1226

o. Baudisch et aI., Naturwiss. 27, 768, 769 (1939); Science 92,336

E. Beckmann, Ber. 19, 988 (1886).

Benzilic Acid Rearrangement

J. Liebig, Ann. 25, 27 (1838); N. Zinin, ibid. 31, 329 (1939).

A. J. Lapworth, J Chern. Soc. 83,995 (1903); 85,1206 (1904).

Bergmann Azlactone Peptide Synthesis eOOH

M. Bergmann et al., Ann. 449,277 (1926).

Bernthsen Acridine Synthesis

M. Betti, Gazz. Chim. Ital. 30 II, 301 (1900); 33 II, 2 (1903);

A. J. Bechamp, Ann. Chim. Phys. 42(3), 186, (1854).

E. Benary, Ber. 63, 1573 (1930); 64,2543 (1931).

P. Biginelli, Ber. 24, 1317,2962 (1891); 26,447 (1893).

Bischler-Mohlau Indole o Synthesis

Bischler- N apieralski Reaction

A. Bischler, B. Napieralski, Ber. 26, 1903 (1893).

Blaise Ketone Synthesis

E. E. Blaise, A. Koehler, Bull. Soc. Chim. [4] 7,215 (1910)

E. E. Blaise, Compt. Rend. 132, 478 (1901).

G. Blanc, Bull. Soc. Chim. France [4],33,313 (1923).

Blanc Reaction-Blanc Rule

H. G. Blanc, Compt. Rend. 144, 1356 (1907).

Bodroux-Chichibabin Aldehyde Synthesis

R. Bohn, DE 46654 (1889); R. E. Schmidt, DE 60855 (1891).

Boord Olefin Synthesis

Bouveault Aldehyde Synthesis

L. Bouveault, Bull. Soc. Chim. France 31, 1306, 1322 (1904).

L. Bouveault, G. Blanc, Compt. Rend. 136, 1676 (1903)

Am. Chern. Soc. 80,933

Copyright © 2005 Nathan T. Reynolds

J Am. Chern. Soc. 62,486 (1940).

A. G. Brook,J. Am. Chern. Soc. 80,1886 (1958)

Bucherer Carbazole Synthesis

H. T. Bucherer, F. Seyde, J. Prakt. Chern. 77(2),403 (1908).

H. T. Bucherer, J Prakt. Chern. [2] 69,49 (1904)

Buchwald-Hartwig Cross Coupling Reaction

w. Chodkiewicz et al., Compt. Rend. 245,322 (1957);

Camps Quinoline Synthesis

88, 129 (1853); K. List, H. Limpricht, Ann. 90, 180

M. F. Carroll, J Chern. Soc. 1940,704; 1941,507

C. E. Castro, R. D. Stephens, J. Org. Chern. 28,2163 (1963)

o. MUlTIlTI et al.,Ber. 48, 379 (1915);