posted on 2013-08-02, 00:00authored byChristian Ruzié, Jolanta Karpinska, Alan R. Kennedy, Yves H. Geerts
The synthesis of 1,6-, 2,7-, 3,8-,
and 4,9-isomers of dibromo-
and didodecyl[1]benzothieno[3,2-b][1]benzothiophenes,
via the stilbene pathway, is described. Starting from the synthesis
of bromo-2-(methylthio)benzaldehydes, a series of functionalization,
McMurry coupling, and finalising cyclization reactions were explored.
The stereochemistry of the cyclization mechanism was investigated.
Using this methodology didodecyl[1]benzothieno[3,2-b][1]benzothiophenes were formed in overall yields of 5–32%.