Journal of Organic Chemistry 2013-08-02

Synthesis of 1,6-, 2,7-, 3,8-, and 4,9-isomers of didodecyl[1]benzothieno[3,2-b][1]benzothiophenes.

Christian Ruzié, Jolanta Karpinska, Alan R Kennedy, Yves H Geerts

文献索引：J. Org. Chem. 78(15) , 7741-8, (2013)

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摘要

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%.