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
UR - http://www.scopus.com/inward/record.url?scp=84881245485&partnerID=8YFLogxK
U2 - 10.1021/jo401134c
DO - 10.1021/jo401134c
M3 - Article
AN - SCOPUS:84881245485
SN - 0022-3263
VL - 78
SP - 7741
EP - 7748
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 15
ER -