Synthesis of Cubane

Structure of Cubane

C8H8

Principal investigatorPhilip E. Eaton
Publication year1964
Synthesis typeTotal
Number of steps 15 (linear)
References
Part 1 of 1
intermediate structure
NBS
CCl4
intermediate structure
Br2
CH2Cl2, Pentane
0 to 10 °C
intermediate structure
Et2NH
Et2O
-20 °C, , 40% (3 steps)
intermediate structure
(CH2OH)2, TsOH
PhH
Reflux
intermediate structure
HCl
H2O
85% (2 steps)
intermediate structure
MeOH
95%
intermediate structure
KOH
H2O
Reflux, , 95%
intermediate structure
SOCl2
intermediate structure
Pyr, t-BuOOH
Et2O
95% (2 steps)
intermediate structure
Cumene
152 °C, , 55%
intermediate structure
H2SO4
H2O
95%
intermediate structure
KOH
H2O
Reflux, , 55%
intermediate structure
SOCl2
intermediate structure
t-BuOOH
Et2O
98% (2 steps)
intermediate structure
Diisopropylbenzene
150 °C, , 30%
intermediate structure