Polybrominated anthracenes: selective synthesis of tetrabromoanthracenes as precursors for the corresponding tetracyanoanthracenes
   
Yazarlar (2)
Doç. Dr. Kıymet BERKİL AKAR Tokat Gaziosmanpaşa Üniversitesi, Türkiye
Osman Çakmak Tokat Gaziosmanpaşa Üniversitesi, Türkiye
Makale Türü Özgün Makale (SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale)
Dergi Adı Tetrahedron Letters (Q4)
Dergi ISSN 0040-4039 Wos Dergi Scopus Dergi
Dergi Tarandığı Indeksler SCI-Expanded
Makale Dili İngilizce Basım Tarihi 01-2013
Cilt / Sayı / Sayfa 54 / 4 / 312–314 DOI 10.1016/j.tetlet.2012.11.048
Makale Linki http://dx.doi.org/10.1016/j.tetlet.2012.11.048
Özet
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.
Anahtar Kelimeler
Anthracene derivative | Bromination | Bromoanthracene | Cyanoanthracene | Organic photoconductor