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

Cakmak O., Aydogan L., Berkil K., GÜLÇİN İ., Buyukgungor O.

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

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 4
  • Basım Tarihi: 2008
  • Doi Numarası: 10.3762/bjoc.4.50
  • Dergi Adı: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Anahtar Kelimeler: anthracene derivative, bromination, bromoanthracene, cyanoanthracene, methoxyanthracene, BLUE ELECTROLUMINESCENCE, FLUORESCENCE PROBES, COLOR PURITY, PROPERTY
  • Atatürk Üniversitesi Adresli: Evet

Özet

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.