Novel Syntheses of Decacyclene by Deoxygenating Cyclotrimerisation of Acenaphthenequinone with Zero-valent Titanium or Phosphorus Pentasulfide

Klaus Zimmermann; Matthias W. Haenel

doi:10.1055/s-1997-3209

Synlett 1997; 1997(5): 609-611
DOI: 10.1055/s-1997-3209

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Novel Syntheses of Decacyclene by Deoxygenating Cyclotrimerisation of Acenaphthenequinone with Zero-valent Titanium or Phosphorus Pentasulfide

Klaus Zimmermann, Matthias W. Haenel^*

^*Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany, Fax +49-208-306-2980; E-mail Haenel@mpi-muelheim.mpg.de

Abstract

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Decacylene (2) was obtained in 15-21% yield by reaction of acenaphthenequinone (6) with bis(η⁶-biphenyl)titanium(0) (9) in toluene or diglyme at 110°C and in 18% yield by reaction of 6 with phosphorus pentasulfide in boiling toluene. The new reactions are used to attempt the conversion of 3,8-dibromoacenaphthenequinone (7) to 3,4,9,10,15,16-hexabromodecacyclene (3) which is considered to serve as a suitable precursor for the bowl-shaped polycyclic aromatic hydrocarbon C₃₆H₁₂ (1).

decacyclene - acenaphthenequinone - deoxygenating cyclotrimerisation - zero-valent titanium - phosphorus pentasulfide

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