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

C. Ruzié, J. Karpinska, A.R. Kennedy, Y.H. Geerts

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22 Citations (Scopus)

Abstract

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%.
Original languageEnglish
Pages (from-to)7741-7748
Number of pages8
JournalJournal of Organic Chemistry
Volume78
Issue number15
DOIs
Publication statusPublished - 2 Aug 2013

Keywords

  • stilbene pathway
  • McMurry coupling
  • cyclization reactions

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