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Named reactions

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Diels-Alder Reaction

Diels-Alder Reaction

Mechanism of the Diels-Alder Reaction

Reference

Original reference Liebigs Ann. 1928, 460, 98.
Wikipedia link
Organic chemistry portal link


Sample reactions

This reaction is from the synthesis of Prostaglandin F2α by Elias J. Corey. Show me the full synthesis.

Reactant structure
2-Chloroacrylonitrile, Cu(BF4)2
Reaction arrow head
0 °C
Product structure

This reaction is from the synthesis of Cubane by Philip E. Eaton. Show me the full synthesis.

Reactant structure
Et2NH
Reaction arrow head
Et2O
-20 °C
40 % (3 steps)
Product structure

This reaction is from the synthesis of Dodecahedrane by Leo A. Paquette. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
THF
-78 °C to RT
23 %
Product structure

This reaction is from the synthesis of Ryanodol by Pierre Deslongchamps. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
PhH
Reflux, 60 min
100 %
Product structure

This reaction is from the synthesis of Reserpine by Robert B. Woodward. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
PhH
Reflux, 10 h
8 %
Product structure

This reaction is from the synthesis of Gelsemine by Larry E. Overman. Show me the full synthesis.

Reactant structure
Methyl acrylate, AlCl3
Reaction arrow head
CH2Cl2
-78 °C, 7 h
98 %
Product structure

This reaction is from the synthesis of Pentacycloanammoxic Acid by Elias J. Corey. Show me the full synthesis.

Reactant structure
DBAD
Reaction arrow head
Product structure

This reaction is from the synthesis of Marasmic Acid by Robert B. Woodward. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
CH2Cl2
RT, 24 h
Product structure + Product structure

This reaction is from the synthesis of Cholesterol by Robert B. Woodward. Show me the full synthesis.

Reactant structure
1,3-Butadiene
Reaction arrow head
PhH
100 °C, 96 h
86 %
Product structure

This reaction is from the synthesis of Carpanone by Orville L. Chapman. Show me the full synthesis.

Reactant structure
PdCl2, NaOAc
Reaction arrow head
MeOH, H2O
38 °C to RT, 3 h
46 %
Product structure

This reaction is from the synthesis of Taxol by Kyriacos C. Nicolaou. Show me the full synthesis.

Reactant structure
2-Chloroacrylonitrile
Sealed tube
Reaction arrow head
PhH
130 °C, 72 h
85 %
Product structure

This reaction is from the synthesis of Taxol by Kyriacos C. Nicolaou. Show me the full synthesis.

Reactant structure + Reactant structure
PhB(OH)2, Neopentyl glycol
Dean-Stark
Reaction arrow head
PhH
RT to Reflux, 48.5 h
61 %
Product structure

This reaction is from the synthesis of Taxol by Isao Kuwajima. Show me the full synthesis.

Reactant structure
O2, Tetraphenylporphyrin
Reaction arrow head
CH2Cl2
RT, 7 h
Product structure

This reaction is from the synthesis of Fredericamycin A by Dale L. Boger. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
CH2Cl2
RT, 20 h
47 % (2 steps)
Product structure

This reaction is from the synthesis of Aspidofractinine by Claude Spino. Show me the full synthesis.

Reactant structure + Reactant structure
Sealed tube
Reaction arrow head
PhH
90 °C, 5 h
55 %
Product structure

This reaction is from the synthesis of Ingenol by John L. Wood. Show me the full synthesis.

Reactant structure + Reactant structure
BF3.OEt2
Reaction arrow head
PhMe
-78 °C, 85 min
59 %
Product structure

This reaction is from the synthesis of Cyanocobalamin by Robert B. Woodward. Show me the full synthesis.

Reactant structure + Reactant structure
SnCl4
Reaction arrow head
PhH
RT
73 %
Product structure

This reaction is from the synthesis of Yohimbine by Eugene E. van Tamelen. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
PhH
RT, 2-3 weeks
93 %
Product structure

This reaction is from the synthesis of Okilactomycin by Amos B. Smith, III. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
PhMe
90 °C, 24 h
88 %
Product structure

This reaction is from the synthesis of Dodecahedrane by Horst Prinzbach. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
CCl4
Reflux, 2 h
100 %
Product structure

This reaction is from the synthesis of Dodecahedrane by Horst Prinzbach. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
PhMe
Reflux, 60 min
92 %
Product structure

This reaction is from the synthesis of Dodecahedrane by Horst Prinzbach. Show me the full synthesis.

Reactant structure
Maleic anhydride
Reaction arrow head
PhH
80 °C, 12 h
98 %
Product structure

This reaction is from the synthesis of Luciduline by Wolfgang Oppolzer. Show me the full synthesis.

Reactant structure + Reactant structure
SnCl4
Reaction arrow head
MeCN
RT, 24 h
Product structure

This reaction is from the synthesis of Reserpine by Gilbert Stork. Show me the full synthesis.

Reactant structure + Reactant structure
i-Pr2NLi
Reaction arrow head
THF
-78 to 0 °C, 3 h
88 %
Product structure

This reaction is from the synthesis of Longifolene by Alex G. Fallis. Show me the full synthesis.

Reactant structure
µW
Reaction arrow head
PhMe
2.5 h
97 %
Product structure

This reaction is from the synthesis of Triquinacene by Leo A. Paquette. Show me the full synthesis.

Reactant structure
I2, DEAD
Reaction arrow head
THF
4.4 %
Product structure

This reaction is from the synthesis of Nominine by David Y. Gin. Show me the full synthesis.

Reactant structure
Pyrrolidine
Reaction arrow head
MeOH
60 °C, 4.5 h
78 %
Product structure

This reaction is from the synthesis of Retigeranic Acid by Elias J. Corey. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
98-105 °C, 120 h
61 %
Product structure

This reaction is from the synthesis of Retigeranic Acid by Tomas Hudlicky. Show me the full synthesis.

Reactant structure
Reaction arrow head
PhMe
300 °C, 8 h
23 %
Product structure + Product structure

This reaction is from the synthesis of Retigeranic Acid by Paul A. Wender. Show me the full synthesis.

Reactant structure
Reaction arrow head
PhMe
250 °C, 22 h
44 %
Product structure

This reaction is from the synthesis of Morphine by Marshall D. Gates. Show me the full synthesis.

Reactant structure
1,3-Butadiene
Reaction arrow head
Dioxane
85-87 °C, 72 h
66 %
Product structure

This reaction is from the synthesis of Mesembrine by Maurice Shamma. Show me the full synthesis.

Reactant structure
1,3-Butadiene
Reaction arrow head
PhMe
Product structure

This reaction is from the synthesis of Caribenol A by Zhen Yang. Show me the full synthesis.

Reactant structure
BHT
Reaction arrow head
PhMe
120 °C, 24 h
92 %
Product structure

This reaction is from the synthesis of Oseltamivir by Elias J. Corey. Show me the full synthesis.

Reactant structure + Reactant structure
Reagent structure
Reaction arrow head
RT, 30 h
97 %
Product structure

This reaction is from the synthesis of Oseltamivir by Tohru Fukuyama. Show me the full synthesis.

Reactant structure
Reagent structureAcrolein
Reaction arrow head
MeCN, H2O
RT, 14 h
Product structure

This reaction is from the synthesis of Morphine by Gilbert Stork. Show me the full synthesis.

Reactant structure
Et3N
Reaction arrow head
Decalin
235-240 °C, 24 h
55 %
Product structure

This reaction is from the synthesis of Strychnine by Albert Padwa. Show me the full synthesis.

Reactant structure
MgI2
µW
Reaction arrow head
PhMe
150 °C, 3 h
95 %
Product structure

This reaction is from the synthesis of Strychnine by Viresh H. Rawal. Show me the full synthesis.

Reactant structure
Sealed tube
Reaction arrow head
PhH
185-200 °C, 4 h
99 %
Product structure

This reaction is from the synthesis of Strychnine by Graham J. Bodwell. Show me the full synthesis.

Reactant structure
Reaction arrow head
PhNEt2
Reflux, 60 min
100 %
Product structure

This reaction is from the synthesis of Strychnine by Christopher D. Vanderwal. Show me the full synthesis.

Reactant structure
KOt-Bu
Sealed tube
Reaction arrow head
THF
80 °C, 3.5 h
64 %
Product structure

This reaction is from the synthesis of Daphnilactone A by Clayton H. Heathcock. Show me the full synthesis.

Reactant structure
NH3
Reaction arrow head
CH2Cl2
0 °C to RT, 60 min
47 % (2 steps)
Product structure

This reaction is from the synthesis of Maritimol by Pierre Deslongchamps. Show me the full synthesis.

Reactant structure
H2O
Reaction arrow head
DMSO
155 °C, 3.5 h
86 %
Product structure

This reaction is from the synthesis of Epibatidine by Andrew C. Regan. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
80-85 °C, 24 h
36 %
Product structure

This reaction is from the synthesis of Strychnine by Stephen F. Martin. Show me the full synthesis.

Reactant structure
Sealed tube
Reaction arrow head
Mesitylene
160 °C, 72 h
85 %
Product structure

This reaction is from the synthesis of Nupharamine by Chihiro Kibayashi. Show me the full synthesis.

Reactant structure
n-Pr4N+ IO4-
Reaction arrow head
CHCl3
0 °C
57 %
Product structure

This reaction is from the synthesis of Nupharamine by José Barluenga. Show me the full synthesis.

Reactant structure + Reactant structure
ZnCl2
Reaction arrow head
THF
-80 °C to RT, 16 h
51 %
Product structure

This reaction is from the synthesis of Cubane by John Tsanaktsidis. Show me the full synthesis.

Reactant structure
NaOH
Reaction arrow head
MeOH
Reflux, 2 h
60 % (2 steps)
Product structure

This reaction is from the synthesis of Hirsutene by Goverdhan Mehta. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
PhH
Reflux, 2 h
90 %
Product structure

This reaction is from the synthesis of Hirsutene by R. Daniel Little. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
Et2O
0 °C, 60 min
100 %
Product structure

This reaction is from the synthesis of Azadirachtin by Steven V. Ley. Show me the full synthesis.

Reactant structure
Hydroquinone, i-Pr2NEt
Reaction arrow head
PhMe
85 °C, 4 h
21 % (2 steps)
Product structure

This reaction is from the synthesis of Epibatidine by David A. Evans. Show me the full synthesis.

Reactant structure + Reactant structure
Me2AlCl
Reaction arrow head
CH2Cl2
-78 °C, 15 min
79 %
Product structure

This reaction is from the synthesis of Centrohexaindane by Dietmar Kuck. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
PhMe
120 °C, 24 h
91 %
Product structure

This reaction is from the synthesis of Hirsutene by Daniel D. Sternbach. Show me the full synthesis.

Reactant structure
Reaction arrow head
Mesitylene
Reflux, 24 h
70 %
Product structure

This reaction is from the synthesis of Corannulene by Jay S. Siegel. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
Ac2O
125 °C, 30 h
74 %
Product structure

This reaction is from the synthesis of Streptonigrone by Dale L. Boger. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
PhH
RT, 3 h
Product structure

This reaction is from the synthesis of Alkaloid GB 13 by Lewis N. Mander. Show me the full synthesis.

Reactant structure + Reactant structure
Reagent structure
Reaction arrow head
110 °C, 3 d
87 %
Product structure
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