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Synlett 1998; 1998(3): 301-303
DOI: 10.1055/s-1998-1627
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Facile Syntheses of 1,8-Bis(diphenylphosphino)anthracene and 1,8-Bis(dimethylamino)anthracene by Nucleophilic Substitution of 1,8-Difluoroanthracene

Matthias W. Haenel* , Stephan Oevers, Joachim Bruckmann, Jörg Kuhnigk, Carl Krüger
  • *Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany; Fax +49-2 08-3 06-29 80; E-mail: Haenel@mpi-muelheim.mpg.de
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Publication History

Publication Date:
31 December 2000 (online)

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1,8-Bis(diphenylphosphino)anthracene (1) was prepared in a three-step synthesis in 51% overall yield starting from 1,8-dichloro-9,10-anthraquinone (8). Compound 8 was converted by chlorine-fluorine exchange and reduction with zinc into 1,8-difluoroanthracene (7) from which 1 was obtained by reaction with potassium 1,8-bis(dimethylamino)anthracene (10) clearly showed that in the case of 7 direct nucleophilic displacement (addition-elimination mechanism) dominates over aryne formation (elimination-addition mechanism). Single crystal X-ray structure analyses are reported for 1 and 10.

anthracene - phosphine - amine - fluoro compound - aromatic nucleophilic substitution