This paper describes a convenient preparation of tetrathia-[7]-helicene (TH[7]), the generation of the α-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-dibenzodithiophene-ethene, 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 α-anion of TH[7], which is easily generated on the α-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.

A convenient procedure for the synthesis of tetrathia-[7]-helicene and the selective α-functionalization of its terminal thiophene ring / S. Maiorana, A. Papagni, E. Licandro, R. Annunziata, P. Paravidino, D. Perdicchia, C. Giannini, M. Bencini, K. Clays, A. Persoons. - In: TETRAHEDRON. - ISSN 0040-4020. - 59:34(2003), pp. 6481-6488.

A convenient procedure for the synthesis of tetrathia-[7]-helicene and the selective α-functionalization of its terminal thiophene ring

S. Maiorana
Primo
;
E. Licandro;R. Annunziata;D. Perdicchia;C. Giannini;
2003

Abstract

This paper describes a convenient preparation of tetrathia-[7]-helicene (TH[7]), the generation of the α-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-dibenzodithiophene-ethene, 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 α-anion of TH[7], which is easily generated on the α-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.
Heterohelicenes; Large-scale preparation; McMurry reaction; NLO properties; Oxidative photocyclisation
Settore CHIM/06 - Chimica Organica
2003
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/187668
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 79
  • ???jsp.display-item.citation.isi??? 78
social impact