Easy access to 3,8-Diaryldifurano[2,3-a:2',3'-f]naphthalenes. A new extended aromatic system.
3,8-Diaryldifurano[2,3-a:2',3'-f]naphthalenes were prepared in two simple steps. First, 1,5-dihydroxynaphthalene and 1-aryl-2-bromodecan-1-ones were condensed to the corresponding naphthalene 1,5-diethers. Second, these intermediates were cyclized using methanesulfonic acid in methylene chloride. Seven examples are given, three of which are doubly substituted with octyl chains to enhance the solubility. This increased solubility allowed further modification of the 3,8-aryl groups to attach electron-withdrawing groups (formyl, nitrile, dicyanovinyl, and benzoyl).
Jørgensen
M
M
Condensed Matter Physics and Chemistry Department, Riso National Laboratory, DK-4000 Roskilde, Denmark. mikkel.joergensen@risoe.dk
Krebs
F C
FC
Bechgaard
K
K