Functionalization of naphthalene: a novel synthetic route to brominated naphthoquinones    
Yazarlar (3)
Osman Çakmak
İstanbul Rumeli Üniversitesi, Türkiye
Doç. Dr. Kıymet BERKİL AKAR Tokat Gaziosmanpaşa Üniversitesi, Türkiye
Nuri Kaplan
Makale Türü Özgün Makale
Makale Alt Türü SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale
Dergi Adı Arkivoc
Dergi ISSN 1551-7012 Wos Dergi Scopus Dergi
Dergi Tarandığı Indeksler SCI-Expanded
Dergi Grubu Q4
Makale Dili İngilizce
Basım Tarihi 05-2012
Cilt No 2012
Sayı 7
Sayfalar 274 / 281
DOI Numarası 10.3998/ark.5550190.0013.718
Makale Linki http://dx.doi.org/10.3998/ark.5550190.0013.718
Özet
An efficient procedure is described for synthesis of 2, 5, 8-tribromonaphthoquinone (12) from naphthalene in four reaction steps. Silver-promoted solvolysis of hexabromide 3 produces the specific diastereostereoisomer 10. Dehydrobromination of 10 using sodium methoxide gives tribromodihydronaphthalene-1, 4-diol 11 in high yield. PCC oxidation of either 10 or 11 results in the formation of 2, 5, 8-tribromonaphthalene-1, 4-dione (12).
Anahtar Kelimeler
Bromonaphthalene | bromination | silver-induced substitution | 1,4-naphthoquinone | PCC oxidation