Cyclotrimerization of benzobarrelene: Synthesis of new isomeric barrelene architectures

Dastan A., Fabris F., De Lucchi O., Guney M., Balci M.

HELVETICA CHIMICA ACTA, vol.86, no.10, pp.3411-3416, 2003 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 86 Issue: 10
  • Publication Date: 2003
  • Doi Number: 10.1002/hlca.200390285
  • Journal Name: HELVETICA CHIMICA ACTA
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.3411-3416
  • Middle East Technical University Affiliated: Yes

Abstract

The cyclotrimerization reaction of benzobarrelene derivatives was investigated. Dibromobenzobarrelene 10 was converted to the bromostannyl derivative 11, which was used as the substrate of the cyclotrimerization reaction. Thus. reaction of 11, with copper(I) thiophene-2-carboxylate (CuTC) gave a mixture of the isomeric cyclotrimers 5 and 6 and the dimers 12 and 13, in addition to a trace of protodestannylated bromoalkene 14 (Scheme 2).