Highly brominated anthracenes as precursors for the convenient synthesis of 2,9,10-trisubstituted anthracene derivatives

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Cakmak O., AYDOĞAN L., BERKİL AKAR K., GÜLÇİN İ., Buyukgungor O.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol.4, 2008 (SCI-Expanded, Scopus) identifier identifier

  • Publication Type: Article / Article
  • Volume: 4
  • Publication Date: 2008
  • Doi Number: 10.3762/bjoc.4.50
  • Journal Name: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Keywords: anthracene derivative, bromination, bromoanthracene, cyanoanthracene, methoxyanthracene, BLUE ELECTROLUMINESCENCE, FLUORESCENCE PROBES, COLOR PURITY, PROPERTY
  • Open Archive Collection: AVESIS Open Access Collection
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

When 9,10-dibromoanthracene was treated with bromine in CCl4 without a catalyst, 1,2,3,4,9,10-hexabromo-1,2,3,4-tetrahydroanthracene (3) was obtained in 95% yield in the absence of other stereoisomers or rearomatization products. We investigated the base-induced elimination reaction of hexabromide 3 under various conditions. Pyridine-induced elimination of hexabromide 3 afforded 2,9,10-tribromoanthracene (12) in 75% yield, and tribromide 12 was transformed to trimethoxy compound 13 and trinitrile 14 by copper-assisted nucleophilic substitution reactions.