CUBANE SYNTHESIS

CubaneCubane (C8H8) is a synthetic hydrocarbon molecule that consists of eight carbon atoms arranged at the corners of a cube, with one hydrogen atom attached to each carbon atom. A solid crystalline substance, cubane is one of the Platonic hydrocarbons. It was first synthesized in 1964 by Philip Eaton, a professor of chemistry at the University of Chicago. Before Eaton and Cole’s work, researchers believed that cubic carbon-based molecules could not exist, because the unusually sharp 90-degree bonding angle of the carbon atoms were expected to be too highly strained, and hence unstable. Once formed, cubane is quite kinetically stable, due to a lack of readily available decomposition paths

References :

Pentane, CH₂Cl₂
0 to 10 °C

Et₂O
-20 °C, 40 % (3 steps)

Diels alder rxn

PhH
Reflux

H₂O
85 % (2 steps)

MeOH
95 %

H₂O
Reflux, 95 %

Favorskii rxn

Et₂O
95 % (2 steps)

Cumene
152 °C, 55 %

H₂O
95 %

H₂O
Reflux, 55 %

Favorskii rxn

Et₂O
98 % (2 steps)