Diels-Alder Reaction

Mechanism of the Diels-Alder Reaction

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Reviews |
Sample reactions

2-Chloroacrylonitrile, Cu(BF4)2
0 °C


Et2NH
Et2O
-20 °C, , 40% (3 steps)



THF
-78 °C to RT, , 23%



PhH
Reflux, 60 min, 100%
"Mixture of isomers."



PhH
Reflux, 10 h, 8%
""[This method was not] investigated extensively with a view to determining optimum conditions.""


Methyl acrylate, AlCl3
CH2Cl2
-78 °C, 7 h, 98%


DBAD



CH2Cl2
RT, 36 h



1,3-Butadiene
PhH
100 °C, 96 h, 86%


NaOAc, PdCl2
H2O, MeOH
38 °C to RT, 3 h, 46%


2-Chloroacrylonitrile
Sealed tube
PhH
130 °C, 72 h, 85%



Neopentyl glycol, PhB(OH)2
Dean-Stark
PhH
RT to Reflux, 48.5 h, 61%


O2, Tetraphenylporphyrin
hν
CH2Cl2
RT, 7 h



CH2Cl2
RT, 20 h, 47% (2 steps)
"95 % yield based on the alkene."



Sealed tube
PhH
90 °C, 5 h, 55%



BF3.OEt2
PhMe
-78 °C, 85 min, 59%
"The product was separated from the resulting three diastereoisomers."



SnCl4
PhH
RT, , 73%
"The enantiomers were resolved with (+)- and (-)-phenylethylamine."



PhH
RT, 2-3 weeks, 93%



PhMe
90 °C, 24 h, 88%



CCl4
Reflux, 2 h, 100%



PhMe
Reflux, 60 min, 92%


Maleic anhydride
PhH
80 °C, 12 h, 98%



SnCl4
MeCN
RT, 24 h



i-Pr2NLi
THF
-78 to 0 °C, 3 h, 88%


µW
PhMe
2.5 h, 97%


DEAD, I2
THF
4.4%


Pyrrolidine
MeOH
60 °C, 4.5 h, 78%



98-105 °C, 120 h, 61%


PhMe
300 °C, 8 h, 23%
"The yield was 76 % brsm."



PhMe
250 °C, 22 h, 44%
"Also isolate was the C14-epimer (24 % yield)."


1,3-Butadiene
Dioxane
85-87 °C, 72 h, 66%


1,3-Butadiene
PhMe
"No yield given."


BHT
PhMe
120 °C, 24 h, 92%



RT, 30 h, 97%


Acrolein
H2O, MeCN
RT, 14 h


Et3N
Decalin
235-240 °C, 24 h, 55%
"The yield was 70 % brsm. Also isolated was the C2-epimer (14 % yield)."


MgI2
µW
PhMe
150 °C, 3 h, 95%


Sealed tube
PhH
185-200 °C, 4 h, 99%


PhNEt2
Reflux, 60 min, 100%


KOt-Bu
Sealed tube
THF
80 °C, 3.5 h, 64%


NH3
CH2Cl2
0 °C to RT, 60 min, 47% (2 steps)


H2O
DMSO
155 °C, 3.5 h, 86%



80-85 °C, 24 h, 36%


Sealed tube
Mesitylene
160 °C, 72 h, 85%


n-Pr4N+ IO4-
CHCl3
0 °C, , 57%
"Also isolated was the C-4a epimer (31 %)"



ZnCl2
THF
-80 °C to RT, 16 h, 51%


NaOH
MeOH
Reflux, 2 h, 60% (2 steps)



PhH
Reflux, 2 h, 90%



Et2O
0 °C, 60 min, 100%


i-Pr2NEt, Hydroquinone
PhMe
85 °C, 4 h, 21% (2 steps)
"The yield was 27 % brsm."



Me2AlCl
CH2Cl2
-78 °C, 15 min, 79%



PhMe
120 °C, 24 h, 91%


Mesitylene
Reflux, 24 h, 70%



Ac2O
125 °C, 30 h, 74%



PhH
RT, 3 h



110 °C, 3 d, 87%



Reflux, 48 h, 82%


PhMe
100 °C, , 30% (2 steps)


Decane
Reflux, 20 h, 71% (2 steps)


1,2,4-Trichlorobenzene
200 °C, 5 h, 67%



SiO2
THF
-78 °C to RT, 8 h


i-Pr2NEt, LiCl
MeCN
RT, 12 h, 55%
"Also produced were 2 other diastereomers (20% yield)"


Et2AlCl, 1,3-Butadiene
CH2Cl2
-78 to -7 °C, 16 h, 56%
