Centrohexaindane

The Propelane Route to Centrohexaindane.

Author	Dietmar Kuck
Publication year	1995
Synthesis type	Total synthesis
Number of steps	6 (linear)
References	J. Chem. Soc., Perkin Trans. 1 1995, 721. J. Org. Chem. 1991, 56, 4753. Chem. Ber. 1994, 127, 409.

Part 1 of 1

BnBr, KF, Celite ®

MeCN
75 °C, 18 h, 89 %

PPA
120 °C, 12-60 h, 91 %

See the Friedel-Crafts Alkylation

Br₂
hν

CCl₄
Reflux, 30 min, 93 %

See the Wohl-Ziegler Reaction

Na₂HPO₄, KH₂PO₄, NaBr

DMSO
80-100 °C, 8 h, 79 %

See the Kornblum Oxidation

PhLi

PhH, Et₂O
40 °C, 6 h

H₃PO₄
Soxhlet (4 Å MS)

Xylene(s)
Reflux, 25-30 h, 40 % (2 steps)

See the Friedel-Crafts Alkylation