title: Highly brominated anthracenes as precursors for the convenient synthesis of 2,9,10-trisubstituted anthracene derivatives.
abstract: When 9,10-dibromoanthracene was treated with bromine in CCl(4) 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.
authors.affiliation: Gaziosmanpasa University, Faculty of Art and Science, Department of Chemistry, TR-60240, Tokat, Turkey. ocakmak@gop.edu.tr
authors.forename: Osman
authors.initials: O
authors.lastname: Cakmak
authors.forename: Leyla
authors.initials: L
authors.lastname: Aydogan
authors.forename: Kiymet
authors.initials: K
authors.lastname: Berkil
authors.forename: Ilhami
authors.initials: I
authors.lastname: Gulcin
authors.forename: Orhan
authors.initials: O
authors.lastname: Buyukgungor