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Cubane

Chemical structure of Cubane
C8H8
Author Philip E. Eaton
Publication year 1964
Synthesis type Total synthesis
Number of steps 15 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
NBS
Arrow head
CCl4


See the Wohl-Ziegler Reaction
Chemical structure
Br2
Arrow head
Pentane, CH2Cl2
0 to 10 °C
Chemical structure
Et2NH
Arrow head
Et2O
-20 °C, 40 % (3 steps)

See the Diels-Alder Reaction
Chemical structure
(CH2OH)2, TsOH
Arrow head
PhH
Reflux
Chemical structure
HCl
Arrow head
H2O
85 % (2 steps)
Chemical structure
hν
Arrow head
MeOH
95 %
Chemical structure
KOH
Arrow head
H2O
Reflux, 95 %

See the Favorskii Rearrangement
Chemical structure
SOCl2
Arrow head
Chemical structure
t-BuOOH, Pyr
Arrow head
Et2O
95 % (2 steps)
Chemical structure
Arrow head
Cumene
152 °C, 55 %
Chemical structure
H2SO4
Arrow head
H2O
95 %
Chemical structure
KOH
Arrow head
H2O
Reflux, 55 %

See the Favorskii Rearrangement
Chemical structure
SOCl2
Arrow head
Chemical structure
t-BuOOH
Arrow head
Et2O
98 % (2 steps)
Chemical structure
Arrow head
Diisopropylbenzene
150 °C, 30 %
Chemical structure

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