Synthesis of Dodecahedrane

Structure of Dodecahedrane

C20H20

Principal investigatorHorst Prinzbach
Publication year1987
Synthesis typeTotal
Number of steps 16 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
CCl4
Reflux, 2 h, 100%
intermediate structure
Li
t-BuOH, THF
Reflux, 15 h, 93%
intermediate structure + intermediate structure
PhMe
Reflux, 60 min, 92%
intermediate structure
Na
Et2O, t-BuOH
Reflux, 16 h, 87%
intermediate structure + intermediate structure
Pd/C
250 °C, 30 min, 61-80%
intermediate structure
2,2,4-Trimethylpentane
RT, 16 h, 26%
"The yield was 99 % brsm."
intermediate structure
Maleic anhydride
PhH
80 °C, 12 h, 98%
intermediate structure
Cu2O, 2,2'-Bipyridine
H2O, Quinoline
Reflux, 40 h, 78%
intermediate structure
  1. BH3.THF
  2. H2O
  3. H2O2
  4. NaOH
THF
0 °C to RT, 4.5 h, 96%
intermediate structure + intermediate structure
CrO3, H2SO4
Acetone, H2O
RT, 2.5 h, 97%
See the Jones Oxidation
intermediate structure + intermediate structure
NaH, HCO2Me
MeOH, THF
RT to 40 °C, 20 h, 100%
intermediate structure + intermediate structure
Et3N, TsN3
THF
RT, 8 h, 90%
intermediate structure + intermediate structure
NaHCO3
H2O, THF
RT, 2 h, 90%
intermediate structure
I2, Pb(OAc)4
CCl4
Reflux, , 80%
See the Kochi Reaction
intermediate structure
Na-K
t-BuOH, THF
RT, ON, 100%
intermediate structure
H2, Pt/Al2O3
315 °C, , 8%
intermediate structure