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

Research output: Contribution to journalArticle

20 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%.
LanguageEnglish
Pages7741-7748
Number of pages8
JournalJournal of Organic Chemistry
Volume78
Issue number15
DOIs
Publication statusPublished - 2 Aug 2013

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Cyclization
Isomers
Benzaldehydes
Stilbenes
Stereochemistry
benzothiophene

Keywords

  • stilbene pathway
  • McMurry coupling
  • cyclization reactions

Cite this

@article{23c15639b22344219278ed645eef4494,
title = "Synthesis of 1,6-, 2,7-, 3,8-, and 4,9-isomers of didodecyl[1] benzothieno[3,2-b][1]benzothiophenes",
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{\%}.",
keywords = "stilbene pathway, McMurry coupling, cyclization reactions",
author = "C. Ruzi{\'e} and J. Karpinska and A.R. Kennedy and Y.H. Geerts",
year = "2013",
month = "8",
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doi = "10.1021/jo401134c",
language = "English",
volume = "78",
pages = "7741--7748",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
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}

Synthesis of 1,6-, 2,7-, 3,8-, and 4,9-isomers of didodecyl[1] benzothieno[3,2-b][1]benzothiophenes. / Ruzié, C.; Karpinska, J.; Kennedy, A.R.; Geerts, Y.H.

In: Journal of Organic Chemistry, Vol. 78, No. 15, 02.08.2013, p. 7741-7748.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of 1,6-, 2,7-, 3,8-, and 4,9-isomers of didodecyl[1] benzothieno[3,2-b][1]benzothiophenes

AU - Ruzié, C.

AU - Karpinska, J.

AU - Kennedy, A.R.

AU - Geerts, Y.H.

PY - 2013/8/2

Y1 - 2013/8/2

N2 - 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%.

AB - 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%.

KW - stilbene pathway

KW - McMurry coupling

KW - cyclization reactions

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U2 - 10.1021/jo401134c

DO - 10.1021/jo401134c

M3 - Article

VL - 78

SP - 7741

EP - 7748

JO - Journal of Organic Chemistry

T2 - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 15

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