Title: A convenient procedure for the synthesis of tetrathia-[7]-helicene and the selective alpha-functionalisation of terminal thiophene ring
Authors: Maiorana, S ×
Papagni, A
Licandro, E
Annunziata, R
Paravidino, P
Perdicchia, D
Giannini, C
Bencini, M
Clays, Koen
Persoons, Andre #
Issue Date: Jan-2003
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:59 issue:34 pages:6481-6488
Abstract: This paper describes a convenient preparation of tetrathia-[7]-helicene (TH[7]), the generation of the alpha-anion on the terminal thiophene ring, and the synthesis of the 2-formyl-tetrathia-[7]-helicene (2-CHO-TH[7]). The key intermediate trans-1,2-dibenzodithiopheneethene, prepared in 97% yield by McMurry coupling of the 2-formyl-benzo[1,2-b;4,3-b']dithiophene, was transformed into TH[7] using a known procedure. The described method affords TH[7] in 46% overall yield, which is more than four times the yield previously reported in the literature. The alpha-anion of TH[7], which is easily generated on the alpha-position of one of the terminal thiophene rings, reacts with electrophilic reagents such as D2O and DMF. The latter reaction proved to be the best way to prepare 2-CHO-TH[7], a key intermediate for the preparation of new substituted heterohelicenes. (C) 2003 Elsevier Ltd. All rights reserved.
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Imaging and Photonics
× corresponding author
# (joint) last author

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