Synthesis of Circulene

Structure of Circulene

C28H14

Principal investigator	Koji Yamamoto
Publication year	1993
Synthesis type	Total
Number of steps	14 (linear)
References	J. Am. Chem. Soc. 1988, 110, 3578. Pure & Appl. Chem. 1993, 65, 157.

Part 1 of 1

intermediate structure

H2O, HCl, Sn

PhMe

Reflux, 5 h, 70%

intermediate structure

NaNO2 , H2SO4
HgBr2 , KBr

H2O

0 °C

intermediate structure

110-120 °C, 2 h, 60% (2 steps)

See the Sandmeyer Reaction

intermediate structure

NBS, Bz2O2

CCl4

Reflux, 3 h, 87%

See the Wohl-Ziegler Reaction

intermediate structure

Thiourea

EtOH

Reflux, 13 h

intermediate structure

NaOH

H2O

Reflux, 8 h, 55% (2 steps)

intermediate structure

Special reagent

Cs2CO3

DMF

50 °C to Reflux, 8 h, 56%

intermediate structure

(MeO)2CHBF4

CH2Cl2

-15 °C to RT, 24 h, 98%

intermediate structure

NaH

THF

50 - 55 °C, 2 d, 67%

See the Stevens Rearrangement

intermediate structure

mCPBA

CHCl3

0 °C to RT, 12 h, 100%

intermediate structure

300 °C, 63%

intermediate structure

I2

hv

Cyclohexane

2 h, 42%

intermediate structure

n-BuLi
DMF

THF

-78 °C to RT, 2 h, 54%

intermediate structure

LiAlH4, TiCl3

CH2Cl2, DME

RT to Reflux, 4.5 h, 35%

See the McMurry Reaction

intermediate structure

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