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

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Ruzié, C. and Karpinska, J. and Kennedy, A.R. and Geerts, Y.H. (2013) Synthesis of 1,6-, 2,7-, 3,8-, and 4,9-isomers of didodecyl[1] benzothieno[3,2-b][1]benzothiophenes. Journal of Organic Chemistry, 78 (15). pp. 7741-7748. ISSN 0022-3263 (https://doi.org/10.1021/jo401134c)

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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%.

ORCID iDs

Ruzié, C., Karpinska, J., Kennedy, A.R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015 and Geerts, Y.H.;
CORE (COnnecting REpositories)