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Polybrominated anthracenes: selective synthesis of tetrabromoanthracenes as precursors for the corresponding tetracyanoanthracenes

Akar, Kiymet Berkil; Cakmak, Osman


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{
  "DOI": "10.1016/j.tetlet.2012.11.048", 
  "abstract": "Selective and efficient methods for the preparation of both 2,7,9,10-tetrabromoanthracene 11 and 2,6,9,10-tetrabromoanthracene 12 are described. Photobromination of 2,9,10-tribromoanthracene 8 resulted in the formation of only one stereoisomeric heptabromide 10. Whilst thermal aromatization of the trans,cis,trans-1,2,3,4,6,9,10-heptabromo-1,2,3,4-tetrahydroanthracene 10 gave mainly 2,6,9, 10-tetrabromoanthracene 12, the pyridine-induced elimination yielded 2,7,9,10-tetrabromoanthracene 11 as the only final product. Tetrabromide 11 was transformed into 2,7,9,10-tetracyanoanthracene 14, by copper-assisted nucleophilic substitution reaction, as a potential photoconductive product. (C) 2012 Elsevier Ltd. All rights reserved.", 
  "author": [
    {
      "family": "Akar", 
      "given": " Kiymet Berkil"
    }, 
    {
      "family": "Cakmak", 
      "given": " Osman"
    }
  ], 
  "container_title": "TETRAHEDRON LETTERS", 
  "id": "15107", 
  "issue": "4", 
  "issued": {
    "date-parts": [
      [
        2013, 
        1, 
        1
      ]
    ]
  }, 
  "page": "312-314", 
  "title": "Polybrominated anthracenes: selective synthesis of tetrabromoanthracenes as precursors for the corresponding tetracyanoanthracenes", 
  "type": "article-journal", 
  "volume": "54"
}
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