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

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)

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%.

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• Item metadata

  Item type:	Article
  ID code:	46006
  Dates:	Date Event 2 August 2013 Published
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	20 Nov 2013 10:03
  Last modified:	08 Apr 2024 20:56
  Related URLs:	Scopus publication
  URI:	https://strathprints.strath.ac.uk/id/eprint/46006