Synthesis of Dodecahedrane

Structure of Dodecahedrane

C20H20

Principal investigator	Horst Prinzbach
Publication year	1987
Synthesis type	Total
Number of steps	16 (linear)
References	Angew. Chem. Int. Ed. 1987, 26, 452. J. Am. Chem. Soc. 1987, 109, 4626.

Part 1 of 1

intermediate structure

+

intermediate structure

CCl4

Reflux, 2 h, 100%

See the Diels-Alder Reaction

intermediate structure

Li

t-BuOH, THF

Reflux, 15 h, 93%

intermediate structure

+

intermediate structure

PhMe

Reflux, 60 min, 92%

See the Diels-Alder Reaction

intermediate structure

Na

Et2O, t-BuOH

Reflux, 16 h, 87%

intermediate structure

+

intermediate structure

Pd/C

250 °C, 30 min, 61-80%

intermediate structure

hν

2,2,4-Trimethylpentane

RT, 16 h, 26%

"The yield was 99 % brsm."

intermediate structure

Maleic anhydride

PhH

80 °C, 12 h, 98%

See the Diels-Alder Reaction

intermediate structure

Cu2O, 2,2'-Bipyridine

H2O, Quinoline

Reflux, 40 h, 78%

intermediate structure

BH3.THF
H2O , H2O2 , NaOH

THF

0 °C to RT, 4.5 h, 96%

intermediate structure

+

intermediate structure

H2SO4, CrO3

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%

See the Claisen Condensation

intermediate structure

+

intermediate structure

Et3N, TsN3

THF

RT, 8 h, 90%

intermediate structure

+

intermediate structure

NaHCO3

hν

H2O, THF

RT, 2 h, 90%

See the Wolff Rearrangement

intermediate structure

I2, Pb(OAc)4

hν

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

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