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
Makale Alt Türü SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale
Dergi Adı Tetrahedron Letters
Dergi ISSN 0040-4039 Wos Dergi Scopus Dergi
Dergi Tarandığı Indeksler SCI-Expanded
Dergi Grubu Q4
Makale Dili İngilizce
Basım Tarihi 01-2013
Cilt No 54
Sayı 4
Sayfalar 312 / 314
DOI Numarası 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 | Bromoanthracene | Bromination | Cyanoanthracene | Organic photoconductor