Synthesis of Cubane

Structure of Cubane

C8H8

Principal investigator	Philip E. Eaton
Publication year	1964
Synthesis type	Total
Number of steps	15 (linear)
References	J. Am. Chem. Soc. 1964, 86, 962. J. Am. Chem. Soc. 1964, 86, 3157.

Part 1 of 1

intermediate structure

NBS

CCl4

See the Wohl-Ziegler Reaction

intermediate structure

Br2

CH2Cl2, Pentane

0 to 10 °C

intermediate structure

Et2NH

Et2O

-20 °C, 40% (3 steps)

See the Diels-Alder Reaction

intermediate structure

TsOH, (CH2OH)2

PhH

Reflux

intermediate structure

HCl

H2O

85% (2 steps)

intermediate structure

hν

MeOH

95%

intermediate structure

KOH

H2O

Reflux, 95%

See the Favorskii Rearrangement

intermediate structure

SOCl2

intermediate structure

t-BuOOH, Pyr

Et2O

95% (2 steps)

intermediate structure

Cumene

152 °C, 55%

intermediate structure

H2SO4

H2O

95%

intermediate structure

KOH

H2O

Reflux, 55%

See the Favorskii Rearrangement

intermediate structure

SOCl2

intermediate structure

t-BuOOH

Et2O

98% (2 steps)

intermediate structure

Diisopropylbenzene

150 °C, 30%

intermediate structure

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