Highly brominated anthracenes as precursors for the convenient synthesis of 2,9,10-trisubstituted anthracene derivatives.
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.
Cakmak
Osman
O
Gaziosmanpasa University, Faculty of Art and Science, Department of Chemistry, TR-60240, Tokat, Turkey. ocakmak@gop.edu.tr
Aydogan
Leyla
L
Berkil
Kiymet
K
Gulcin
Ilhami
I
Buyukgungor
Orhan
O