Synthesis of Centrohexaindane

Structure of Centrohexaindane

C41H24

Principal investigator	Dietmar Kuck
Publication year	1995
Synthesis type	Total
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

intermediate structure

BnBr, Celite, KF

MeCN

75 °C, 18 h, 89%

intermediate structure

PPA

120 °C, 12-60 h, 91%

See the Friedel-Crafts Alkylation

intermediate structure

Br2

hν

CCl4

Reflux, 30 min, 93%

See the Wohl-Ziegler Reaction

intermediate structure

KH2PO4, Na2HPO4, NaBr

DMSO

80-100 °C, 8 h, 79%

See the Kornblum Oxidation

intermediate structure

PhLi

Et2O, PhH

40 °C, 6 h

intermediate structure

H3PO4

Soxhlet (4 Å MS)

Xylene(s)

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

See the Friedel-Crafts Alkylation

intermediate structure

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