Facile Syntheses of 1,8-Bis(diphenylphosphino)anthracene and 1,8-Bis(dimethylamino)anthracene by Nucleophilic Substitution of 1,8-Difluoroanthracene

Authors:
  • MHMatthias W. Haenel
    Matthias W. Haenel
  • SOStephan Oevers
    Stephan Oevers
  • JBJoachim Bruckmann
    Joachim Bruckmann
  • JKJörg Kuhnigk
    Jörg Kuhnigk
  • CKCarl Krüger
    Carl Krüger
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Abstract
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.