Synthesis of Centrohexaindane

Structure of Centrohexaindane

C41H24

Principal investigator	Dietmar Kuck
Publication year	1988
Synthesis type	Total
Number of steps	11 (linear)
References	Angew. Chem. Int. Ed. 1988, 26, 1192. J. Am. Chem. Soc. 1986, 108, 8107. Chem. Ber. 1994, 127, 409.

Part 1 of 1

intermediate structure

+

intermediate structure

AcOH

100 °C, 60 min, 63%

See the Michael Addition

intermediate structure

LiAlH4

THF

Reflux, 8 h, 88%

intermediate structure

H3PO4

Dean-Stark

Xylene(s)

Reflux, 2 h, 91%

See the Friedel-Crafts Alkylation

intermediate structure

H2SO4, CrO3

Acetone, H2O

RT, 12 h, 94%

See the Jones Oxidation

intermediate structure

Br2

AcOH

RT, ON, 85%

intermediate structure

KOH

THF

RT to Reflux, 17 h, 70-85%

See the Favorskii Rearrangement

intermediate structure

Cu

Quinoline

200 °C, 10 h, 33-38%

intermediate structure

+

intermediate structure

PhMe

120 °C, 24 h, 91%

See the Diels-Alder Reaction

intermediate structure

Na

t-BuOH, THF

Reflux, 16 h, 82%

intermediate structure

Br2

hν

CCl4

RT, 20 min, 63%

See the Wohl-Ziegler Reaction

intermediate structure

AlBr3

PhH

40 °C to Reflux, 42 h, 80%

See the Friedel-Crafts Alkylation

intermediate structure

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