Synthesis of Corannulene

Structure of Corannulene

C20H10

Principal investigatorRichard G. Lawton
Publication year1971
Synthesis typeTotal
Number of steps 12 (linear)
References
J. Am. Chem. Soc. 1971, 93, 1730.
Part 1 of 1
intermediate structure
NBS
CCl4
Reflux, 12 h, 92%
See the Wohl-Ziegler Reaction
"The starting material is obtained in 5 steps from acenaphthene, see: Chem. Ber. 1963, 96, 1098."
intermediate structure + intermediate structure
KOt-Bu
PhH, t-BuOH
45-55 °C, 60 min
intermediate structure
KOH
MeOH
Reflux, 6.5 h, 97% (2 steps)
intermediate structure
PPA
85 °C, 60 min, 73%
See the Friedel-Crafts Acylation
intermediate structure
HClO4, Pd/C, H2
3 atm
AcOH, H2O
RT, 22 h, 54%
intermediate structure
CH2N2
Et2O
RT, 3 h, 93%
intermediate structure
Na
Et2O, MeOH, NH3
-78 °C, 15 min, 48%
See the Acyloin Condensation
intermediate structure
NaBH4
n-PrOH
RT, 90 min
intermediate structure
HCl
AcOH, H2O
Reflux, 5 min
See the Pinacol Rearrangement
intermediate structure
Vacuum
100 °C, 10.5 h, 92% (2 steps)
intermediate structure
NaBH4
EtOH, PhH
RT, 30 min, 94%
intermediate structure
Pd/C
100 to 275 °C, 2 h, 16%
intermediate structure
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